Document:

Form of Warrant

 Exhibit 10.3 
 THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE BEEN ACQUIRED FOR INVESTMENT AND HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR ANY STATE SECURITIES LAW. SUCH SECURITIES MAY NOT BE
SOLD OR TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR UNLESS SUCH SALE OR TRANSFER IS EXEMPT FROM THE REGISTRATION AND PROSPECTUS DELIVERY REQUIREMENTS OF THE ACT OR THE ISSUER HAS RECEIVED AN OPINION OF COUNSEL IN FORM AND SUBSTANCE REASONABLY
ACCEPTABLE TO THE ISSUER THAT REGISTRATION IS NOT REQUIRED UNDER THE ACT OR APPLICABLE STATE SECURITIES LAWS. THESE SECURITIES AND THE SECURITIES ISSUABLE UPON EXERCISE OF THESE SECURITIES MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN
ACCOUNT SECURED BY SUCH SECURITIES. 
 eDiets.com, Inc. 
 Warrant for the Purchase of Shares of 
 Common Stock

  

			
	No. 2	  	 178,218 Shares
 Original Issue Date: August 1, 2006

 FOR VALUE RECEIVED, eDiets.com, Inc., a Delaware corporation (the “Company”),
hereby certifies that Prides Capital Fund I, L.P., is entitled to purchase from the Company, at any time or from time to time commencing on the six (6) month anniversary of the Original Issue Date (the “Initial Exercise Date”)
and expiring at 5:00 P.M., New York City time, on the five (5) year anniversary of the Original Issue Date (the “Expiration Date”) ONE HUNDRED SEVENTY EIGHT THOUSAND TWO HUNDRED EIGHTEEN (178,218) fully paid and
non-assessable shares of Common Stock, par value $.001 per share, of the Company (the “Warrant Shares”) for a per share exercise price of $6.00 (the “Per Share Warrant Price”). The Per Share Warrant Price is subject
to adjustment as hereinafter provided. Capitalized terms used and not otherwise defined in this Warrant shall have the meanings specified in Section 8, unless the context otherwise requires. 
 1. Exercise of Warrant. 
 (a) This
Warrant may be exercised, in whole at any time or in part from time to time, commencing on the Initial Exercise Date and expiring at 5:00 P.M., New York City time, on the Expiration Date (with the Exercise Notice at the end of this Warrant duly
executed) at the address set forth in Section 10 hereof, together with payment of the Per Share Warrant Price multiplied by the number of Warrant Shares to which such exercise relates made by delivery to the Company of one or more types of
Permitted Consideration. 
 (b) If this Warrant is exercised in part, the Company will deliver to the Holder within three Trading Days of
the date such Holder delivers to the 

 
Company this Warrant and an Exercise Notice, together with the payment of the aggregate Per Share Warrant Price for such exercise, a new Warrant covering the
Warrant Shares that have not been exercised. By the expiration of the third Trading Day following the Holder’s delivery of a Warrant, together with an Exercise Notice and the payment of the aggregate Per Share Warrant Price for such exercise,
the Company will (i) issue a certificate or certificates in the name of the Holder for the largest number of whole shares of the Common Stock to which the Holder shall be entitled and, if this Warrant is exercised in whole, in lieu of any
fractional share of the Common Stock to which the Holder shall be entitled, pay to the Holder cash in an amount equal to the fair value of such fractional share (determined by reference to the closing sales price of the Common Stock on the date of
the Exercise Notice), and (ii) deliver the other securities and properties receivable upon the exercise of this Warrant, or the proportionate part thereof if this Warrant is exercised in part, pursuant to the provisions of this Warrant.

 (c) If, by the third Trading Day after the date that the Holder delivers an Exercise Notice, together with the payment of the aggregate
Per Share Warrant Price for such exercise, the Company fails to deliver the required number of Warrant Shares in the manner required pursuant to Section 1(b), then the Holder will have the right to rescind such exercise. 
 (d) If, by the third Trading Day after the date that the Holder delivers an Exercise Notice, together with the payment of the aggregate Per Share
Warrant Price for such exercise, the Company fails to deliver the required number of Warrant Shares in the manner required pursuant to Section 1(b), and if after such third Trading Day and prior to the receipt of such Warrant Shares, the Holder
purchases (in an open market transaction or otherwise) shares of Common Stock to deliver in satisfaction of a sale by the Holder of the Warrant Shares which the Holder anticipated receiving upon such exercise (a “Buy-In”), then the
Company shall (1) pay in cash to the Holder the amount by which (x) the Holder’s total purchase price (including brokerage commissions, if any) for the shares of Common Stock so purchased exceeds (y) the amount obtained by
multiplying (A) the number of Warrant Shares that the Company was required to deliver to the Holder in connection with the exercise at issue by (B) the closing bid price of the Common Stock at the time of the obligation giving rise to such
purchase obligation and (2) at the option of the Holder, either reinstate the portion of the Warrant and equivalent number of Warrant Shares for which such exercise was not honored or deliver to the Holder the number of shares of Common Stock
that would have been issued had the Company timely complied with its exercise and delivery obligations hereunder. The Holder shall provide the Company written notice indicating the amounts payable to the Holder in respect of the Buy-In. 

(e) If, after the Effectiveness Date (as defined in the Registration Rights Agreement) the Warrant Shares to be issued are not registered and
available for resale by the Holder pursuant to a registration statement in accordance with the Registration Rights Agreement, then notwithstanding anything contained herein to the contrary, the Holder may, at its election exercised in its sole
discretion, exercise a portion of this Warrant with respect to an aggregate total of twenty-five percent (25%) of the total Warrant Shares and, in lieu of making a cash payment of Permitted Consideration, elect instead to receive upon such
exercise the “Net Number” of shares of Common Stock determined according to the following formula: 
  

					
	Net Number =	 	 (A x B) – (A x C)
	  	
		 	B	  	

  

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 For purposes of the foregoing formula: 
 A=the total number of Warrant Shares with respect 
 to which this Warrant is then being exercised. 
 B=the average of the closing sales prices for the
five 
 Trading Days immediately prior to (but not including) 
 the day that the Holder delivers the Exercise Notice at issue. 
 C=the Per Share Warrant Price.

 2. Company’s Option to Change Expiration Date. 
 Notwithstanding anything herein to the contrary, in the event that (i) the closing sales price per share of Common Stock is in excess of 200% of the Per Share Warrant Price (as may be adjusted pursuant to
Section 3) for sixty (60) consecutive Trading Days, (ii) the Warrant Shares are either registered for resale pursuant to an effective registration statement naming the Holder as a selling stockholder thereunder (and the prospectus
thereunder is available for use by the Holder as to all then available Warrant Shares) or freely transferable without volume restrictions pursuant to Rule 144(k) promulgated under the Securities Act, as determined by counsel to the Company pursuant
to a written opinion letter addressed and in form and substance reasonably acceptable to the Holder and the transfer agent for the Common Stock, during the entire sixty (60) Trading Day period referenced in (i) above through the expiration
of the Call Date as set forth in the Company’s notice pursuant to this Section (the “Call Condition Period”), and (iii) the Company shall have complied in all material respects with its obligations under this Warrant and
under the Purchase Agreement and the Common Stock shall at all times be listed on the AMEX, New York Stock Exchange, the Nasdaq National Market, the Nasdaq Capital Market or the OTC Bulletin Board, then, subject to the conditions set forth in this
Section, the Company may, in its sole discretion, elect to change the Expiration Date for the respective Warrant to 5:00 P.M., New York City time on the date that is thirty (30) days after written notice thereof (a “Call
Notice”) is received by the Holder (the “Call Date”) at the address last shown on the records of the Company for the Holder or given by the Holder to the Company for the purpose of notice; provided, that the conditions to
giving such notice must be in effect at all times during the Call Condition Period or any such notice shall be null and void. Notwithstanding anything herein to the contrary, if the Company changes the Expiration Date pursuant to this
Section 2, the Holder may, at its election exercised in its sole discretion, exercise a portion of this Warrant with respect to an aggregate total (including any exercises made under Section 1(e)) of twenty-five percent (25%) of the
total Warrant Shares and, in lieu of making a cash payment of Permitted Consideration, elect instead to receive upon such exercise the “Net Number” of shares of Common Stock determined according to the formula set forth in
Section 1(e). 
 3. Certain Adjustments. The Per Share Warrant Price and number of Warrant Shares issuable upon exercise of this
Warrant are subject to adjustment from time to time as set forth in this Section 3. 
 (a) If the Company, at any time while this
Warrant is outstanding, (i) pays a stock dividend on its Common Stock or otherwise makes a distribution on any class of capital stock that is payable in shares of Common Stock, (ii) subdivides outstanding shares of Common Stock into a
larger number of shares, or (iii) combines outstanding shares of Common Stock into a smaller number of shares, then in each such case the Per Share Warrant Price shall be multiplied by a fraction of which the numerator shall be the number of
shares of Common Stock outstanding immediately before such event and of which the denominator shall be the number of shares of Common Stock 

  

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outstanding immediately after such event. Any adjustment made pursuant to clause (i) of this paragraph shall become effective immediately after the
record date for the determination of shareholders entitled to receive such dividend or distribution, and any adjustment pursuant to clause (ii) or (iii) of this paragraph shall become effective immediately after the effective date of such
subdivision or combination. 
 (b) If, at any time while this Warrant is outstanding, (1) the Company effects any merger or
consolidation of the Company with or into another person, (2) the Company effects any sale of all or substantially all of its assets in one or a series of related transactions, (3) any tender offer or exchange offer (whether by the Company
or another Person) is completed pursuant to which holders of Common Stock are permitted to tender or exchange their shares for other securities, cash or property, or (4) the Company effects any reclassification of the Common Stock or any
compulsory share exchange pursuant to which the Common Stock is effectively converted into or exchanged for other securities, cash or property (in any such case, a “Fundamental Transaction”), then thereafter this Warrant shall
represent the right to receive, upon exercise of this Warrant, the same amount and kind of securities, cash or property as it would have been entitled to receive upon the occurrence of such Fundamental Transaction if it had been, immediately prior
to such Fundamental Transaction, the holder of the number of Warrant Shares then issuable upon exercise in full of this Warrant (the “Alternate Consideration”). For purposes of any such exercise, the determination of the Per Share
Warrant Price shall be appropriately adjusted to apply to such Alternate Consideration based on the amount of Alternate Consideration issuable in respect of one share of Common Stock in such Fundamental Transaction, and the Company shall apportion
the Per Share Warrant Price among the Alternate Consideration in a reasonable manner reflecting the relative value of any different components of the Alternate Consideration. If holders of Common Stock are given any choice as to the securities, cash
or property to be received in a Fundamental Transaction, then the Holder shall be given the same choice as to the Alternate Consideration it receives upon any exercise of this Warrant following such Fundamental Transaction. At the Holder’s
option and request, any successor to the Company or surviving entity (and, if an entity different from the successor or surviving entity, the entity whose capital stock or assets the Holders of Common Stock are entitled to receive as a result of
such Fundamental Transaction) in such Fundamental Transaction shall, either (1) issue to the Holder a new warrant substantially in the form of this Warrant and consistent with the foregoing provisions and evidencing the Holder’s right to
purchase the Alternate Consideration for the aggregate Per Share Warrant Price upon exercise thereof, or (2) purchase the Warrant from the Holder for a purchase price, payable in cash within five trading days after such request (or, if later,
on the effective date of the Fundamental Transaction), equal to the Black Scholes value of the remaining unexercised portion of this Warrant on the date of such request. The terms of any agreement pursuant to which a Fundamental Transaction is
effected shall include terms requiring any such successor or surviving entity (and, if an entity different from the successor or surviving entity, the entity whose capital stock or assets the Holders of Common Stock are entitled to receive as a
result of such Fundamental Transaction) to comply with the provisions of this paragraph (b) and insuring that the Warrant (or any such replacement security) will be similarly adjusted upon any subsequent transaction analogous to a Fundamental
Transaction. 
 (c) All calculations under this Section 3 shall be made to the nearest cent or the nearest 1/100th of a share, as applicable. The number of shares of Common Stock outstanding at any given time shall not include shares owned
or held by or for the account of the Company. 
  

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 (d) Upon the occurrence of each adjustment pursuant to this Section 3, the Company at its expense
will promptly compute such adjustment in accordance with the terms of this Warrant and prepare a certificate setting forth such adjustment, including a statement of the adjusted Per Share Warrant Price and adjusted number or type of Warrant Shares
or other securities issuable upon exercise of this Warrant (as applicable), describing the transactions giving rise to such adjustments and showing in detail the facts upon which such adjustment is based. The Company will promptly deliver a copy of
each such certificate to the Holder and to the Company’s transfer agent. 
 4. Fully Paid Stock; Taxes. 
 The Company agrees that the shares of Common Stock represented by each and every certificate for Warrant Shares delivered on the exercise of this Warrant
shall at the time of such delivery, be duly authorized, validly issued and outstanding, fully paid and nonassessable, and not subject to preemptive rights or rights of first refusal, and the Company will take all such actions as may be necessary to
assure that the par value or stated value, if any, per share of the Common Stock is at all times equal to or less than the then Per Share Warrant Price. The Company further covenants and agrees that it will pay, when due and payable, any and all
Federal and state stamp, original issue or similar taxes which may be payable in respect of the issue of any Warrant Share or any certificate thereof to the extent required because of the issuance by the Company of such security. 
 5. Registration Under Securities Act. 
 (a) The Holder shall, with respect to the Warrant Shares, have the registration rights set forth in the Registration Rights Agreement. By acceptance of this Warrant, the Holder agrees to comply with the provisions of the Registration Rights
Agreement. 
 (b) Until the later of (i) such time as the Holder shall be eligible to resell all of its Warrant Shares without volume
restrictions pursuant to Rule 144(k) promulgated under the Securities Act (assuming Holder is not an “affiliate” of the Company, as defined in Rule 144), as evidenced by a legal opinion to such effect delivered by the Company’s
counsel and acceptable to each of the Company’s transfer agent and the Holder, or (ii) the date on which all Warrant Shares have been sold under a Registration Statement or pursuant to Rule 144 (“Rule 144”) as promulgated
under the Securities Act, the Company shall use its reasonable best efforts to file with the Securities and Exchange Commission all current reports and the information as may be necessary to enable the Holder to effect sales of the Warrant Shares in
reliance upon Rule 144 promulgated under the Securities Act. 
 6. Investment Intent; Restrictions on Transferability.  
 (a) The Holder represents, by accepting this Warrant that it understands that this Warrant and any securities obtainable upon exercise of this Warrant
have not been registered for sale under Federal or state securities laws and are being offered and sold to the Holder pursuant to one or more exemptions from the registration requirements of such securities laws. Certificates representing Warrant
Shares may, for so long as required in accordance with the Purchase Agreement, bear the restrictive legend set forth on the first page hereof. The Holder understands that the Holder must bear the economic risk of such Holder’s investment in
this Warrant and any Warrant Shares or other securities obtainable upon exercise of this Warrant for an indefinite period of time, as this Warrant and such Warrant shares or other securities have not been registered under Federal or state securities
laws and therefore cannot be sold unless subsequently registered under such laws, or an exemption from such registration is available. 
  

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 (b) The Holder, by such Holder’s acceptance of this Warrant, represents to the Company that such
Holder is acquiring this Warrant and will acquire any Warrant Shares or other securities obtainable upon exercise of this Warrant for such Holder’s own account for investment and not with a view to, or for sale in connection with, any
distribution thereof in violation of the Securities Act. The Holder agrees that this Warrant and any such Warrant Shares or other securities will not be sold or otherwise transferred unless (i) a registration statement with respect to such
transfer is effective under the Securities Act or (ii) such sale or transfer is made pursuant to one or more exemptions from the Securities Act. 
 7. Loss, Theft, Destruction or Mutilation of Warrant. 
 Upon receipt of evidence satisfactory to the
Company of the loss, theft, destruction or mutilation of this Warrant, and of indemnity reasonably satisfactory to the Company, if lost, stolen or destroyed, and upon surrender and cancellation of this Warrant, if mutilated, the Company shall
execute and deliver to the Holder, a new Warrant of like date, tenor and denomination. 
 8. Warrant Holder Not Stockholder.

 This Warrant does not confer upon the Holder any right to vote or to consent to or receive notice as a stockholder of the Company, as such,
in respect of any matters whatsoever, or any other rights or liabilities as a stockholder, prior to the exercise hereof; this Warrant does, however, require certain notices to Holders as set forth herein. 
 9. Definitions. 
 In addition to the
terms defined elsewhere in this Warrant, the following terms have the following meanings: 
 “Closing Date” shall have the
meaning given such term in the Securities Purchase Agreement. 
 “Common Stock” shall mean the Common Stock, par value $.001
per share, of the Company, for which the Warrant is exercisable and any securities into which such common stock may hereafter be classified. 
 “Exchange Act” means the Securities Exchange Act of 1934, as amended. 
 “Holder” shall mean the
holder of this Warrant and “Holders” shall mean the holder of this Warrant and the holders of all other Warrants. 
 “Majority of the Holders” shall mean Holders of Warrants representing more than fifty percent (50%) of the shares of Common Stock obtainable upon exercise of the Warrants then outstanding. 
 “Permitted Consideration” shall mean (a) cash or other funds immediately available to the Company. 
  

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 “Securities Purchase Agreement” shall mean that certain Securities Purchase Agreement,
dated as of May 15, 2006 by and between the Company and the Investor named therein, pursuant to which, among other things, the initial Holder purchased this Warrant. 
 “Registration Rights Agreement” shall mean that certain Registration Rights Agreement, dated as of May 15, 2006, by and between the Company and the Investor party thereto. 
 “Securities Act” means the Securities Act of 1933, as amended. 
 “Trading Day” means (i) a day on which the Common Stock is traded on a Trading Market (other than the OTC Bulletin Board), or
(ii) if the Common Stock is not listed on a Trading Market, a day on which the Common Stock is traded in the over the counter market, as reported by the OTC Bulletin Board, or (iii) if the Common Stock is not quoted on the OTC Bulletin
Board, a day on which the Common Stock is quoted in the over the counter market as reported by the National Quotation Bureau Incorporated (or any similar organization or agency succeeding to its functions of reporting prices); provided, that in the
event that the Common Stock is not listed or quoted as set forth in (i), (ii) and (iii) hereof, then Trading Day shall mean a Business Day. 
 “Warrants” shall mean this Warrant, all similar Warrants issued on the date hereof and all warrants hereafter issued in exchange or substitution for this Warrant or such similar Warrants. 

10. Communication. 
 All notices
and communications hereunder shall be in writing and shall be deemed to be duly given if sent by registered or certified mail, return receipt requested, via a national recognized overnight mail delivery service, or by facsimile (provided the sender
receives a machine-generated confirmation of successful transmission), if to the Company, to: 
 eDiets.com, Inc. 
 3801 W. Hillsboro Blvd. 
 Deerfield Beach,
Florida 33442 
 Attn: General Counsel 
 Fax: (954) 360-9022 
 With a copy to (except in the case of Exercise Notices, Assignments and Partial Assignments):

 Edwards Angell Palmer & Dodge LLP 
 350 E. Las Olas Boulevard 
 Suite 1150 
 Fort Lauderdale, Florida 33301-4215 
 Attn:
Leslie J. Croland, P.A. 
 Fax: (904) 727-2601 
 If to the Holder of this Warrant, to such Holder at the address listed on the records of the Company. 
  

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 11. Reservation of Warrant Shares; Listing. 
 The Company shall at all times prior to the Expiration Date (a) have authorized and in reserve, and shall keep available, solely for issuance and
delivery upon the exercise of this Warrant, the shares of the Common Stock and other securities and properties as from time to time shall be receivable upon the exercise of this Warrant, free and clear of all restrictions on sale or transfer, other
than under Federal or state securities laws, and free and clear of all preemptive rights and rights of first refusal; and (b) use its reasonable best efforts to keep the Warrant Shares authorized for listing on any national securities exchange,
the Nasdaq National Market, the Nasdaq Capital Market or the OTC Bulletin Board. 
 12. Headings; Severability. 
 The headings of this Warrant have been inserted as a matter of convenience and shall not affect the construction hereof. In case any one or more of the
provisions of this Warrant shall be invalid or unenforceable in any respect, the validity and enforceability of the remaining terms and provisions of this Warrant shall not in any way be affected or impaired thereby and the parties will attempt in
good faith to agree upon a valid and enforceable provision which shall be a commercially reasonable substitute therefor, and upon so agreeing, shall incorporate such substitute provision in this Warrant. 
 13. Applicable Law. 
 This Warrant
shall be governed by and construed in accordance with the law of the State of Delaware without giving effect to the principles of conflicts of law thereof. 
 14. Specific Performance. The Company agrees that the remedies at law of the Holder of this Warrant in the event of any default or threatened default by the Company in the performance of or compliance with any
of the terms of this Warrant are not and will not be adequate and that, to the fullest extent permitted by law, such terms maybe specifically enforced by a decree for the specific performance of any obligation contained herein or by an injunction
against a violation of any of the terms hereof or otherwise. 
 15. Amendment, Waiver, etc. 
 Except as expressly provided herein, neither this Warrant nor any term hereof may be amended, waived, discharged or terminated other than by a written
instrument signed by the party against whom enforcement of any such amendment, waiver, discharge or termination is sought. 
 [Signature
Page Follows] 
  

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 IN WITNESS WHEREOF, the Company has caused this Warrant to be duly signed by its undersigned duly
authorized officer as of the Original Issue Date first above referenced. 
  

			
	eDiets.com, Inc.
		
	By:	 	 /s/ Robert T. Hamilton

	Name:	 	Robert T. Hamilton
	Title:	 	Chief Financial Officer

 ATTEST: 
  

	
	 /s/ James Epstein

	Secretary
	[Corporate Seal]

  

 - 9 - 

 ASSIGNMENT 
 FOR VALUE RECEIVED                      hereby sells, assigns and transfers unto
                     the foregoing Warrant and all rights evidenced thereby, and does irrevocably constitute and appoint
                    , attorney, to transfer said Warrant on the books of eDiets.com, Inc. 
  

					
	Dated:                     	 		 	Signature:
                                       
 
			
		 		 	Address:
                                       
 

 PARTIAL ASSIGNMENT 
 FOR VALUE RECEIVED                      hereby
assigns and transfers unto                      the right to purchase
                     shares of the Common Stock, par value $.001 per share, of eDiets.com, Inc. covered by the foregoing Warrant, and a
proportionate part of said Warrant and the rights evidenced thereby, and does irrevocably constitute and appoint                     ,
attorney, to transfer that part of said Warrant on the books of eDiets.com, Inc. 
  

					
	Dated:                     	 		 	Signature:
                                       
 
			
		 		 	Address:
                                       
 

  

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 EXERCISE NOTICE 
 The undersigned hereby elects to purchase                      shares of Common Stock of eDiets.com, Inc.
pursuant to the attached Warrant, and, if such Holder is not utilizing the cashless (or net) exercise provisions set forth in the Warrant, encloses herewith
$                     in cash, certified or official bank check or checks or other immediately available funds, which sum represents the
aggregate Per Share Warrant Price for the number of shares of Common Stock to which this Exercise Notice relates, together with any applicable taxes payable by the undersigned pursuant to the Warrant. 
 By its delivery of this Exercise Notice, the undersigned represents and warrants to the Company that it is an “accredited investor” as defined in Rule 501(a)
under the Securities Act of 1933. 
 The undersigned requests that certificates for the shares of Common Stock issuable upon this exercise be issued in the
name of:
                                        .

  

					
	Date:                     	 	  

		 	Signature
		 	Name:	 	  

		 	Address:	 	  

		 		 	  

		
		 	Social Security or Tax I.D. Number:
			
		 		 	  

  

 - 11 -Underwriting Agreement

 Exhibit 10.1 
 CNA Financial Corporation 
 7,000,000 Shares 
 Common Stock 
 ($2.50 par value per share) 
 Underwriting Agreement 
  

					
	 	 	 	 	New York, New York
		 		 	August 1, 2006

 To the Representatives 
 named in Schedule I hereto 
 of the several Underwriters named 
 in Schedule II hereto 
 Ladies and Gentlemen: 
 CNA
Financial Corporation, a Delaware corporation (the “Company”), proposes to sell to the several underwriters named in Schedule II hereto (the “Underwriters”), for whom you (the “Representatives”) are acting as
representatives, 7,000,000 shares of its Common Stock, $2.50 par value per share (“Common Stock”) (said shares to be issued and sold by the Company being hereinafter called the “Securities”). To the extent there are no additional
Underwriters listed on Schedule II other than you, the term Representatives as used herein shall mean you, as Underwriters, and the terms Representatives and Underwriters shall mean either the singular or plural as the context requires. Any
reference herein to the Registration Statement, the Basic Prospectus, any Preliminary Final Prospectus or the Final Prospectus shall be deemed to refer to and include the documents incorporated by reference therein pursuant to Item 12 of Form
S-3 which were filed under the Exchange Act on or before the Effective Date of the Registration Statement or the issue date of the Basic Prospectus, any Preliminary Final Prospectus or the Final Prospectus, as the case may be; and any reference
herein to the terms “amend”, “amendment” or “supplement” with respect to the Registration Statement, the Basic Prospectus, any Preliminary Final Prospectus or the Final Prospectus shall be deemed to refer to and include
the filing of any document under the Exchange Act after the Effective Date of the Registration Statement, or the issue date of the Basic Prospectus, any Preliminary Final Prospectus or the Final Prospectus, as the case may be, deemed to be
incorporated therein by reference. Certain terms used herein are defined in Section 20 hereof. 
 1. Representations and Warranties. The Company
represents and warrants to, and agrees with, each Underwriter that: 
 (a) The Company meets the requirements for use of Form
S-3 under the Act and has prepared and filed with the Commission a registration statement (the file number of which is set forth in Schedule I hereto) on Form S-3, including a related basic prospectus, for registration under the Act of the offering
and sale of the Securities. Such Registration Statement, including any amendments thereto filed prior to the Execution Time, have been declared effective by the Commission. The Company may have filed with the Commission, as part of an amendment to
the Registration Statement or pursuant to Rule 424(b), one or more Preliminary Final Prospectuses, each of which has previously been furnished to you. The Company will file with the Commission a final prospectus supplement relating to the Securities
in accordance with Rule 424(b). As filed, such final prospectus supplement shall contain all information required by the Act and the rules thereunder, and, except to the extent the Representatives shall agree in writing to a modification, shall be
in all substantive respects in the form furnished to you prior to the Execution Time or, to the extent not completed at the Execution Time, shall contain only such specific additional information and other changes (beyond that contained in the Basic
Prospectus and any Preliminary Final Prospectus) as the Company has advised you, prior to the Execution Time, will be included or made therein. The Registration Statement, at the Execution Time, meets the requirements set forth in Rule 415(a)(1)(x).

 (b) On the Effective Date, the Registration Statement did or will, and when the Final
Prospectus is first filed (if required) in accordance with Rule 424(b) and on the Closing Date (as defined herein), the Final Prospectus (and any supplement thereto) will, comply in all material respects with the applicable requirements of the
Act and the Exchange Act and the respective rules thereunder; on the Effective Date and at the Execution Time, the Registration Statement did not contain any untrue statement of a material fact or omit to state any material fact required to be
stated therein or necessary in order to make the statements therein not misleading; and as of its date and on the Closing Date and any settlement date, the Final Prospectus (together with any supplement thereto) will not, include any untrue
statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading; provided, however, that the Company makes no
representations or warranties as to the information contained in or omitted from the Registration Statement or the Final Prospectus (or any supplement thereto) in reliance upon and in conformity with information furnished in writing to the Company
by or on behalf of any Underwriter through the Representatives specifically for inclusion in the Registration Statement or the Final Prospectus (or any supplement thereto), it being understood and agreed that the only such information furnished by
or on behalf of any Underwriters consists of the information described as such in Section 8(b) hereof. 
 (c) As of the
Applicable Time, the Disclosure Package, when taken together as a whole, does not contain any untrue statement of a material fact or omit to state any material fact necessary in order to make the statements therein, in the light of the circumstances
under which they were made, not misleading. The preceding sentence does not apply to statements in or omissions from the Disclosure Package based upon and in conformity with written information furnished to the Company by any Underwriter through the
Representatives specifically for use therein, it being understood and agreed that the only such information furnished by or on behalf of any Underwriter consists of the information described as such in Section 8(b) hereof. 
 (d) The Company agrees, unless previously paid, to pay the fees required by the Commission relating to the Securities. 
 (e) At the earliest time after the filing of the Registration Statement that the Company or another offering participant made a bona
fide offer (within the meaning of Rule 164(h)(2)) relating to the Securities, the Company was not and is not an Ineligible Issuer (as defined in Rule 405), without taking account of any determination by the Commission pursuant to Rule 405 that
it is not necessary that the Company be considered an Ineligible Issuer. 
 (f) As of the time of its first use, each Issuer
Free Writing Prospectus does not or will not include any information that conflicts with the information contained in the Registration Statement, including any document incorporated therein and any prospectus supplement deemed to be a part thereof
that has not been superseded or modified. The foregoing sentence does not apply to statements in or omissions from the Disclosure Package based upon and in conformity with written information furnished to the Company by any Underwriter through the
Representatives specifically for use therein, it being understood and agreed that the only such information furnished by or on behalf of any Underwriter consists of the information described as such in Section 8(b) hereof. 
 (g) The Company has been duly incorporated and is validly existing as a corporation in good standing under the laws of the State of
Delaware with full corporate power and authority to own or lease, as the case may be, and to operate its properties and conduct its business as described in the Disclosure Package and the Final Prospectus, and other than as could not, individually
or in the aggregate, reasonably be expected to have a Material Adverse Effect, is duly qualified to do business as a foreign corporation and is in good standing under the laws of each jurisdiction which requires such qualification. 
 (h) Each of the Material Subsidiaries is validly existing as an insurance company (other than The Continental Corporation, which is
validly existing as a New York business corporation, and CNA 
  

 2 

 Surety Corporation, which is in good standing as a Delaware corporation) and is authorized to transact
its appropriate business under the insurance code of its domiciliary state, with full corporate power and authority to own is properties and conduct its business as described in the Disclosure Package and the Final Prospectus, and is duly licensed
to do business as a foreign insurer and is authorized to transact its appropriate business under the laws of each jurisdiction which requires such licensure wherein it owns or leases material properties or conducts material business where the
failure to be so licensed could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. 
 (i) All the outstanding shares of capital stock of each Material Subsidiary have been duly and validly authorized and issued and are fully paid and nonassessable, and, except as otherwise set forth in the Disclosure Package and the Final
Prospectus, all outstanding shares of capital stock of the Material Subsidiaries are owned by the Company either directly or through wholly owned subsidiaries (except for CNA Surety Corporation, of which the Company owns approximately 63%) free and
clear of any security interests, claims, liens or encumbrances, except where the existence of any such security interest, claim, lien or encumbrance, could not, individually or in the aggregate, reasonably be expected to have a Material Adverse
Effect. 
 (j) The Company’s authorized equity capitalization is as set forth in the Disclosure Package and the Final
Prospectus; the capital stock of the Company conforms in all material respects to the description thereof contained in the Disclosure Package and the Final Prospectus; the Securities have been duly and validly authorized and when issued and
delivered and paid for by the Underwriters pursuant to this Agreement will be fully paid and nonassessable; the Securities have been authorized for listing upon notice of issuance on the New York Stock Exchange; the certificates for the Securities
are in valid and sufficient form; the holders of outstanding shares of capital stock of the Company are not entitled to preemptive or other rights to subscribe for the Securities; and, except as set forth in the Disclosure Package and the Final
Prospectus, no options, warrants or other rights to purchase, agreements or other obligations to issue, or rights to convert any obligations into or exchange any securities for, shares of capital stock of or ownership interests in the Company are
outstanding. 
 (k) There is no franchise, contract or other document of a character required to be described in the
Registration Statement, the Disclosure Package or the Final Prospectus, or to be filed as an exhibit thereto, which is not described or filed as required. 
 (l) This Agreement has been duly authorized, executed and delivered by the Company and constitutes a valid and binding obligation of the Company enforceable in accordance with its terms (except as rights to
indemnification and contribution hereunder may be limited by applicable law and subject, as to the enforcement of remedies, to applicable bankruptcy, reorganization, insolvency, moratorium or other laws affecting creditors’ rights generally
from time to time in effect and to general principles of equity, including, without limitation, concepts of materiality, reasonableness, good faith and fair dealing, regardless of whether considered in a proceeding in equity or at law). 

(m) The Company is not and, after giving effect to the offering and sale of the Securities and the application of the proceeds thereof
as described in the Final Prospectus will not be, an “investment company” as defined in the Investment Company Act of 1940, as amended. 
 (n) No consent, approval, authorization, filing with or order of any court or governmental agency or body is required to be obtained by the Company in connection with the transactions contemplated herein, except such
as have been or will be obtained under the Act and the Exchange Act and such as may be required under the blue sky laws of any jurisdiction in connection with the purchase and distribution of the Securities by the Underwriters in the manner
contemplated herein and in the Disclosure Package and the Final Prospectus. 
 (o) Neither the issue and sale of the
Securities (including the application of the proceeds therefrom as described in the Final Prospectus) nor the consummation of any other of the transactions herein contemplated nor the fulfillment of the terms hereof will conflict with, result in a
breach or violation or imposition of any lien, charge or encumbrance upon any property or assets of the Company or any of its 
  

 3 

 Material Subsidiaries pursuant to, (i) the charter or by-laws of the Company or any of its Material
Subsidiaries, (ii) the terms of any indenture, contract, lease, mortgage, deed of trust, note agreement, loan agreement or other agreement, obligation, condition, covenant or instrument to which the Company or any of its Material Subsidiaries
is a party or bound or to which its or their property is subject, or (iii) any statute, law, rule, regulation, judgment, order or decree applicable to the Company or any of its Material Subsidiaries of any court, regulatory body, administrative
agency, governmental body, arbitrator or other authority having jurisdiction over the Company or any of its Material Subsidiaries or any of its or their properties, except, with respect to clauses (ii) and (iii) above, for such conflicts,
breaches, violations or impositions that could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. 
 (p) No holders of securities of the Company have rights to the registration of such securities under the Registration Statement. 
 (q) The consolidated historical financial statements of the Company and its consolidated subsidiaries included or incorporated by
reference in the Final Prospectus, the Disclosure Package and the Registration Statement present fairly in all material respects the financial condition, results of operations and cash flows of the Company as of the dates and for the periods
indicated, comply as to form with the applicable accounting requirements of the Act and the Exchange Act and have been prepared in conformity with generally accepted accounting principles applied on a consistent basis throughout the periods involved
(except as otherwise noted therein). The selected financial data set forth under the caption “Selected Financial Data” in the Company’s Annual Report on Form 10-K for the year ended December 31, 2005 (the “Annual
Report”) fairly present in all material respects, on the basis stated in the Annual Report, the information included therein. 
 (r) No action, suit or proceeding by or before any court or governmental agency, authority or body or any arbitrator involving the Company or any of its subsidiaries or its or their property is pending or, to the knowledge of the Company,
threatened that (i) could reasonably be expected to have a material adverse effect on the performance of this Agreement or the consummation of any of the transactions contemplated hereby or (ii) could reasonably be expected to have a
Material Adverse Effect except, in the case of (i) and (ii), as set forth in or contemplated in the Disclosure Package and the Final Prospectus (exclusive of any supplement thereto). 
 (s) Except as could not reasonably be expected to have a Material Adverse Effect, each of the Company and each of its Material
Subsidiaries owns or leases all such properties as are necessary to the conduct of its operations as presently conducted. 
 (t) Neither the Company nor any subsidiary is in violation or default of (i) any provision of its charter or bylaws, (ii) the terms of any indenture, contract, lease, mortgage, deed of trust, note agreement, loan agreement or
other agreement, obligation, condition, covenant or instrument to which it is a party or bound or to which its property is subject (except in any case in which such violation or default could not reasonably be expected to have a Material Adverse
Effect, and except as set forth in or contemplated in the Disclosure Package and the Final Prospectus (exclusive of any supplement thereto)), or (iii) any statute, law, rule, regulation, judgment, order or decree of any court, regulatory body,
administrative agency, governmental body, arbitrator or other authority having jurisdiction over the Company or such subsidiary or any of its properties, as applicable (except in any case in which such violation or default could not reasonably be
expected to have a Material Adverse Effect, and except as set forth in or contemplated in the Disclosure Package and the Final Prospectus (exclusive of any supplement thereto)). 
 (u) Deloitte & Touche LLP, who have certified certain financial statements of the Company and its consolidated subsidiaries and
delivered their reports with respect to the audited consolidated financial statements and schedules included or incorporated by reference in the Disclosure Package and the Final Prospectus, are independent registered public accountants with respect
to the Company within the meaning of the Act and the applicable published rules and regulations thereunder. 
  

 4 

 (v) There are no transfer taxes or other similar fees or charges under Federal law or the
laws of any state, or any political subdivision thereof, required to be paid by the Company in connection with the execution and delivery of this Agreement or the issuance or sale by the Company of the Securities. 
 (w) Except as could not reasonably be expected to have a Material Adverse Effect, and except as set forth in or contemplated in the
Disclosure Package and the Final Prospectus (exclusive of any supplement thereto), no labor problem or dispute with the employees of the Company or any of its Material Subsidiaries exists or, to the Company’s knowledge, is threatened or
imminent, and the Company is not aware of any existing or imminent labor disturbance by the employees of any of its or its Material Subsidiaries’ principal suppliers, contractors or customers. 
 (x) The Company and its Material Subsidiaries possess all licenses, certificates, permits and other authorizations issued by the
appropriate federal, state or foreign regulatory authorities necessary to conduct their respective businesses, except where the failure to possess such a license, certificate, permit and other authorization could not, individually or in the
aggregate, reasonably be expected to have a Material Adverse Effect, and neither the Company nor any such subsidiary has received any notice of proceedings relating to the revocation or modification of any such certificate, authorization or permit
which, singly or in the aggregate, if the subject of an unfavorable decision, ruling or finding, could reasonably be expected to have a Material Adverse Effect, except as set forth in or contemplated in the Disclosure Package and the Final
Prospectus (exclusive of any supplement thereto). 
 (y) Except as disclosed in the Disclosure Package and the Final
Prospectus, the Company has not taken, directly or indirectly, any action designed to or that would constitute or that might reasonably be expected to cause or result in, under the Exchange Act or otherwise, stabilization or manipulation of the
price of any security of the Company to facilitate the sale or resale of the Securities. 
 (z) The Company and its Material
Subsidiaries own, possess, license or have other rights to use, on reasonable terms, all material patents, patent rights, licenses, inventions, copyrights, know how (including trade secrets and other unpatented and/or unpatentable proprietary or
confidential information, systems or procedures), trademarks, service marks and trade names (collectively, the “Intellectual Property”) currently employed by them in connection with the businesses of the Company and its Material
Subsidiaries as now conducted or as proposed in the Disclosure Package and the Final Prospectus to be conducted, except where the failure to so own, possess, license or otherwise use on reasonable terms could not, singly or in the aggregate,
reasonably be expected to have a Material Adverse Effect on the Company and its subsidiaries, taken as a whole. Except as could not reasonably be expected to have a Material Adverse Effect, to the Company’s knowledge: (a) there are no
rights of third parties to any such Intellectual Property; (b) there is no material infringement by third parties of any such Intellectual Property; (c) there is no pending or, to the Company’s knowledge, threatened action, suit,
proceeding or claim by others challenging the rights of the Company or any of its Material Subsidiaries in or to any such Intellectual Property, and the Company and each of its Material Subsidiaries is unaware of any facts which would form a
reasonable basis for any such claim; (d) there is no pending or threatened action, suit, proceeding or claim by others challenging the validity or scope of any such Intellectual Property, and the Company and each of its Material Subsidiaries is
unaware of any facts which would form a reasonable basis for any such claim; and (e) there is no pending or, to the Company’s knowledge, threatened action, suit, proceeding or claim by others that the Company or any of its Material
Subsidiaries infringes or otherwise violates any patent, trademark, copyright, trade secret or other proprietary rights of others, and the Company and each of its Material Subsidiaries is unaware of any other fact which would form a reasonable basis
for any such claim. 
 (aa) There has been no failure in any material respect on the part of the Company and, to the
Company’s knowledge, any of the Company’s directors or officers, in their capacities as such, to comply with any provision of the Sarbanes Oxley Act of 2002 and the rules and regulations promulgated in connection therewith (the
“Sarbanes Oxley Act”). 
 (bb) Except as disclosed in the Registration Statement, the Disclosure Package and the
Final Prospectus, the Company maintains disclosure controls and procedures (as such term is defined in Rule 13a-15 under the Exchange Act) that are effective in all material respects in providing reasonable assurance 
  

 5 

 that information required to be disclosed by the Company in the reports that it files or submits under
the Exchange Act is recorded, processed, summarized and reported, within the time periods specified in the rules and forms of the Commission, including, without limitation, controls and procedures designed to ensure that information required to be
disclosed by the Company in the reports that it files or submits under the Exchange Act is accumulated and communicated to the Company’s management, including its principal executive officer or officers and its principal financial officer or
officers, as appropriate to allow timely decisions regarding required disclosure. Except as disclosed in the Registration Statement, the Disclosure Package and the Final Prospectus, the Company maintains a system of internal control over financial
reporting sufficient to provide reasonable assurance that (i) transactions are executed in accordance with management’s general or specific authorization; (ii) transactions are recorded as necessary to permit preparation of financial
statements in conformity with US GAAP and to maintain accountability for assets; (iii) access to assets is permitted only in accordance with management’s general or specific authorization; and (iv) the recorded accountability for
assets is compared with existing assets at reasonable intervals and appropriate action is taken with respect to any differences. 
 (cc) Each Material Subsidiary of the Company that is engaged in the business of insurance or reinsurance (each an “Insurance Subsidiary”, collectively the “Insurance Subsidiaries”) is licensed or authorized to conduct an
insurance or reinsurance business, as the case may be, under the insurance statutes of each jurisdiction in which the conduct of its business requires such licensing or authorization, except for such jurisdictions in which the failure of the
Insurance Subsidiary to be so licensed or authorized could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. The Company and the Insurance Subsidiaries have made all required filings under applicable
insurance statutes in each jurisdiction where such filings are required, except for such filings the failure of which to make could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. Each of the
Insurance Subsidiaries has all other necessary authorizations, approvals, orders, consents, certificates, permits, registrations and qualifications (“Authorizations”), of and from all insurance regulatory authorities necessary to conduct
their respective existing businesses as described in the Disclosure Package and the Final Prospectus, except where the failure to have such Authorizations could not, individually or in the aggregate, reasonably be expected to have a Material Adverse
Effect, and no Insurance Subsidiary has received any notification from any insurance regulatory authority to the effect that any additional Authorizations are needed to be obtained by any Insurance Subsidiary in any case where it could reasonably be
expected that the failure to obtain such additional Authorizations or the limiting of the writing of such business, individually or in the aggregate, would have a Material Adverse Effect, and, except as described in the Disclosure Package and the
Final Prospectus, no insurance regulatory authority having jurisdiction over any Insurance Subsidiary has issued any order or decree impairing, restricting or prohibiting (i) the payment of dividends by any Insurance Subsidiary to its parent,
other than those restrictions applicable to insurance or reinsurance companies under such jurisdiction generally, or (ii) the continuation of the business of the Company or any of the Insurance Subsidiaries in all material respects as presently
conducted, in each case except where such orders or decrees could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. 
 (dd) Except as described in the Disclosure Package and the Final Prospectus, (i) all ceded reinsurance and retrocessional treaties,
contracts, agreements and arrangements (“Reinsurance Contracts”) to which the Company or any Insurance Subsidiary is a party and as to which any of them reported recoverables, premiums due or other amounts in its most recent statutory
financial statements are in full force and effect, except where the failure of such Reinsurance Contracts to be in full force and effect could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect, and
(ii) neither the Company nor any Reinsurance Subsidiary has received any notice from any other party to any Reinsurance Contract that such other party intends not to perform such Reinsurance Contract in any material respect, and the Company has
no knowledge that any of the other parties to such Reinsurance Contracts will be unable to perform their respective obligations thereunder in any material respect, except where (A) the Company or the Insurance Subsidiary has established
reserves in its financial statements which it deems adequate for potential uncollectible reinsurance or (B) such nonperformance could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect. 

 

 6 

 (ee) Except as described in the Disclosure Package and the Final Prospectus, the Company
has no knowledge of any threatened or pending downgrading of the Company’s or any of its subsidiaries’ claims-paying ability rating or financial strength rating by A.M. Best Company, Inc., Standard & Poor’s Rating Group,
Moody’s Investor Service, Inc., Fitch Ratings, Ltd. or any other “nationally recognized statistical rating organizations,” as such term is defined for purposes of Rule 436(g)(2) under the Securities Act, which currently has publicly
released a rating of the claims-paying ability or financial strength of the Company or any subsidiary. 
 (ff) The repurchase
by the Company of its Series H Cumulative Preferred Stock, no par value, will not violate any insurance or other law, rule, regulation or other order applicable to the Company or any of its Material Subsidiaries, except for any such violations that
could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect.. 
 (gg) Except as
disclosed in the Registration Statement, the Disclosure Package and the Final Prospectus, the Company does not intend to use any of the proceeds from the sale of the Securities hereunder to repay any outstanding debt (other than publicly traded debt
securities of the Company) owed to any affiliate of any of the Underwriters. 
 Any certificate signed by any officer of the Company and
delivered to the Representatives or counsel for the Underwriters in connection with the offering of the Securities shall be deemed a representation and warranty by the Company, as to matters covered thereby, to each Underwriter. 
 2. Purchase and Sale. Subject to the terms and conditions and in reliance upon the representations and warranties herein set forth, the Company agrees to sell to
each Underwriter, and each Underwriter agrees, severally and not jointly, to purchase from the Company, at the purchase price set forth in Schedule I hereto, the number of Securities set forth opposite such Underwriter’s name in Schedule II
hereto. 
 3. Delivery and Payment. Delivery of and payment for the Securities shall be made on the date and at the time specified in Schedule I
hereto, or at such time on such later date not more than three Business Days after the foregoing date as the Representatives shall designate, which date and time may be postponed by agreement between the Representatives and the Company or as
provided in Section 9 hereof (such date and time of delivery and payment for the Securities being herein called the “Closing Date”). Delivery of the Securities shall be made to the Representatives for the respective accounts of the
several Underwriters against payment by the several Underwriters through the Representatives of the purchase price thereof to or upon the order of the Company by wire transfer payable in same-day funds to an account specified by the Company.
Delivery of the Securities shall be made through the facilities of The Depository Trust Company unless the Representatives shall otherwise instruct. 
 4.
Offering by Underwriters. It is understood that the several Underwriters propose to offer the Securities for sale to the public as set forth in the Final Prospectus. 
 5. Agreements. The Company agrees with the several Underwriters that: 
 (a) Prior to the termination
of the offering of the Securities, the Company will not file any amendment of the Registration Statement or supplement (including the Final Prospectus or any Preliminary Final Prospectus) to the Basic Prospectus unless the Company has furnished you
a copy for your review prior to filing and will not file any such proposed amendment or supplement to which you reasonably object in writing. The Company will cause the Final Prospectus, properly completed, and any supplement thereto to be filed in
a form approved by the Representatives (which approval shall not be unreasonably withheld) with the Commission pursuant to the applicable paragraph of Rule 424(b) (without reliance on Rule 424(b)(8)) within the time period therein prescribed and
will provide evidence satisfactory to the Representatives of such timely filing. The Company will promptly advise the Representatives (1) when the Final Prospectus, and any supplement thereto, shall have been filed (if required) with the
Commission pursuant to Rule 424(b), (2) when, prior to termination of the offering of the Securities, any amendment to the Registration Statement shall have been filed or become effective, (3) of any request by the Commission or its staff
for any amendment of the Registration Statement, or for any supplement to the Final Prospectus or for any additional information, (4) of the issuance by the Commission of any stop order suspending the 
  

 7 

 effectiveness of the Registration Statement or of any notice pursuant to Rule 401(g)(2) of the Act that
would prevent its use or the institution or threatening of any proceeding for that purpose and (5) of the receipt by the Company of any notification with respect to the suspension of the qualification of the Securities for sale in any
jurisdiction or the institution or threatening of any proceeding for such purpose. The Company will use its reasonable best efforts to prevent the issuance of any such stop order or the occurrence of any such suspension or prevention and, upon such
issuance, occurrence or prevention, to obtain as soon as possible the withdrawal of such stop order or relief from such occurrence or prevention, including, if necessary, by filing an amendment to the Registration Statement or a new registration
statement and using its reasonable best efforts to have such amendment or new registration statement declared effective as soon as practicable. 
 (b) If there occurs an event or development as a result of which the Disclosure Package would include an untrue statement of a material fact or would omit to state a material fact necessary in order to make the statements therein, in the
light of the circumstances then prevailing, not misleading, the Company will notify promptly the Representatives so that any use of the Disclosure Package may cease until it is amended or supplemented. 
 (c) If, at any time when a prospectus relating to the Securities is required to be delivered under the Act (including in circumstances where such
requirement may be satisfied pursuant to Rule 172), any event occurs as a result of which the Final Prospectus as then supplemented would include any untrue statement of a material fact or omit to state any material fact necessary to make the
statements therein in the light of the circumstances under which they were made not misleading, or if it shall be necessary to amend the Registration Statement, file a new registration statement or supplement the Final Prospectus to comply with the
Act or the Exchange Act or the respective rules thereunder, including in connection with use or delivery of the Final Prospectus, the Company promptly will (1) notify the Representatives of such event, (2) prepare and file with the
Commission, subject to the second sentence of paragraph (a) of this Section 5, an amendment or supplement or new registration statement which will correct such statement or omission or effect such compliance, (3) use its reasonable
best efforts to have any amendment to the Registration Statement or new registration statement declared effective as soon as practicable in order to avoid any disruption in use of the Final Prospectus and (4) supply any supplemented Final
Prospectus to you in such quantities as you may reasonably request. 
 (d) As soon as practicable, the Company will make generally available
to its security holders and to the Representatives an earnings statement or statements of the Company and its subsidiaries which will satisfy the provisions of Section 11(a) of the Act and Rule 158. 
 (e) The Company will furnish to the Representatives and counsel for the Underwriters, without charge, conformed copies of the Registration Statement
(including exhibits thereto) and to each other Underwriter a copy of the Registration Statement (without exhibits thereto) and, so long as delivery of a prospectus by an Underwriter or dealer may be required by the Act (including in circumstances
where such requirement may be satisfied pursuant to Rule 172), as many copies of each Preliminary Final Prospectus, the Final Prospectus and each Issuer Free Writing Prospectus and any supplement thereto as the Representatives may reasonably
request. 
 (f) The Company will use its reasonable best efforts to arrange, if necessary, for the qualification of the Securities for sale
under the laws of such jurisdictions as the Representatives may designate and will maintain such qualifications in effect so long as required for the distribution of the Securities; provided that in no event shall the Company be obligated to qualify
to do business in any jurisdiction where it is not now so qualified or to take any action that would subject it to service of process in suits, other than those arising out of the offering or sale of the Securities, in any jurisdiction where it is
not now so subject or take any action which would subject the Company to taxation in any jurisdiction where it is not already subject to taxation. 
 (g) The Company agrees that, unless it obtains the prior written consent of the Representatives, and each Underwriter, severally and not jointly, agrees with the Company that, unless it obtains the prior written consent of the Company, it
has not made and will not make any offer relating to the Securities that 
  

 8 

 would constitute an Issuer Free Writing Prospectus or that would otherwise constitute a “free
writing prospectus” (as defined in Rule 405) required to be filed by the Company with the Commission or retained by the Company under Rule 433; provided that the prior written consent of the parties hereto shall be deemed to have been given in
respect of the Free Writing Prospectuses including the information contained in Schedule III hereto. Any such free writing prospectus consented to by the Representatives or the Company is hereinafter referred to as a “Permitted Free Writing
Prospectus.” The Company agrees that (x) it has treated and will treat, as the case may be, each Permitted Free Writing Prospectus as an Issuer Free Writing Prospectus and (y) it has complied and will comply, as the case may be, with
the requirements of Rules 164 and 433 applicable to any Permitted Free Writing Prospectus, including in respect of timely filing with the Commission, legending and record keeping. 
 (h) The Company will not, without the prior written consent of the Representatives, offer, sell, contract to sell, pledge, or otherwise dispose of (or
enter into any transaction which is designed to, or might reasonably be expected to, result in the disposition (whether by actual disposition or effective economic disposition due to cash settlement or otherwise) by the Company or any affiliate of
the Company or any person in privity with the Company or any affiliate of the Company) directly or indirectly, including the filing (or participation in the filing) of a registration statement with the Commission in respect of, or establish or
increase a put equivalent position or liquidate or decrease a call equivalent position within the meaning of Section 16 of the Exchange Act, any other shares of Common Stock or any securities convertible into, or exercisable, or exchangeable for,
shares of Common Stock; or publicly announce an intention to effect any such transaction, for a period of 90 days after the date of the Underwriting Agreement, provided, however, that (i) the Company may issue and/or sell shares of Common Stock to
Loews Corporation and (ii) the Company may issue options, grant stock appreciation rights and sell Common Stock pursuant to any employee stock option plan, stock ownership plan, incentive compensation plan or dividend reinvestment plan of the
Company in effect at the Execution Time or as described in the Disclosure Package and the Final Prospectus. 
 (i) Except as disclosed in the
Disclosure Package and the Final Prospectus, the Company will not take, directly or indirectly, any action designed to or that would constitute or that might reasonably be expected to cause or result in, under the Exchange Act or otherwise,
stabilization or manipulation of the price of any security of the Company to facilitate the sale or resale of the Securities. 
 (j) The
Company agrees to pay the costs and expenses relating to the following matters: (i) the preparation, printing or reproduction and filing with the Commission of the Registration Statement (including financial statements and exhibits thereto), the
Basic Prospectus, each Preliminary Final Prospectus, the Final Prospectus and each Issuer Free Writing Prospectus, and each amendment or supplement to any of them; (ii) the printing (or reproduction) and delivery (including postage, air freight
charges and charges for counting and packaging) of such copies of the Registration Statement, the Basic Prospectus, each Preliminary Final Prospectus, the Final Prospectus and each Issuer Free Writing Prospectus, and all amendments or supplements to
any of them, as may, in each case, be reasonably requested for use in connection with the offering and sale of the Securities; (iii) the preparation, printing, authentication, issuance and delivery of certificates for the Securities, including any
stamp or transfer taxes in connection with the original issuance and sale of the Securities; (iv) the printing (or reproduction) and delivery of this Agreement, any blue sky memorandum and all other agreements or documents printed (or reproduced)
and delivered in connection with the offering of the Securities; (v) the listing of the Securities on the New York Stock Exchange; (vi) any registration or qualification of the Securities for offer and sale under the securities or blue sky laws of
the several states (including filing fees and the reasonable fees and expenses of counsel, up to $5,000, for the Underwriters relating to such registration and qualification); (vii) any filings required to be made with the National Association of
Securities Dealers, Inc. (including filing fees and the reasonable fees and expenses of counsel to the Underwriters related to such filings; (viii) the fees and expenses of the Company’s accountants and the fees and expenses of counsel
(including local and special counsel) for the Company; and (ix) all other costs and expenses incident to the performance by the Company of its obligations hereunder. 
 6. Conditions to the Obligations of the Underwriters. The obligations of the Underwriters to purchase the Securities shall be subject to the accuracy of the representations and warranties on the part of the
Company 
  

 9 

 contained herein as of the Execution Time and the Closing Date, to the accuracy of the statements of the Company made in
any certificates pursuant to the provisions hereof, to the performance by the Company of its obligations hereunder and to the following additional conditions: 
 (a) The Final Prospectus, and any supplement thereto, have been filed in the manner and within the time period required by Rule 424(b) (without reliance on Rule 424(b)(8)); any other material required to be filed by
the Company pursuant to Rule 433(d) under the Act, shall have been filed with the Commission within the applicable time periods prescribed for such filings by Rule 433; and no stop order suspending the effectiveness of the Registration Statement or
any notice pursuant to Rule 401(g)(2) of the Act that would prevent its use shall have been issued and no proceedings for that purpose shall have been instituted or, to the Company’s knowledge, threatened. 
 (b) The Company shall have requested and caused Mayer, Brown, Rowe & Maw LLP, counsel for the Company, to have furnished to the Representatives
their opinion and letter, in each case dated the Closing Date and addressed to the Representatives, in the form of Exhibit A. 
 In
rendering such opinion, such counsel may rely (A) as to matters involving the application of laws of any jurisdiction other than the State of New York, the General Corporation Law of Delaware or the Federal laws of the United States, to the
extent they deem proper and specified in such opinion, upon the opinion of other counsel of good standing whom they believe to be reliable and who are satisfactory to counsel for the Underwriters; and (B) as to matters of fact, to the extent
they deem proper, on certificates of responsible officers of the Company and public officials. Such opinion may contain customary assumptions, exceptions, limitations, qualifications and comments. 
 (c) The Company shall have requested and caused Jonathan D. Kanter, Executive Vice President, General Counsel and Secretary for CNA Financial Corporation,
to have furnished his opinion, dated the Closing Date and addressed to the Representatives in the form of Exhibit B. 
 In rendering such
opinion, such counsel may rely (A) as to matters involving the application of laws of any jurisdiction other than the States of New York and Illinois, the General Corporation Law of Delaware or the Federal laws of the United States, to the
extent he deems proper and specified in such opinion, upon the opinion of other counsel of good standing whom he believes to be reliable and who are satisfactory to counsel for the Underwriters; and (B) as to matters of fact, to the extent he
deems proper, on certificates of responsible officers of the Company and public officials. Such opinion may contain customary assumptions, exceptions, limitations, qualifications and comments. 
 (d) The Representatives shall have received from Cravath, Swaine & Moore LLP, counsel for the Underwriters, such opinion or opinions, dated the
Closing Date and addressed to the Representatives, with respect to the issuance and sale of the Securities, the Registration Statement, the Disclosure Package, the Final Prospectus (together with any supplement thereto) and other related matters as
the Representatives may reasonably require, and the Company shall have furnished to such counsel such documents as they reasonably request for the purpose of enabling them to pass upon such matters. 
 (e) The Company shall have furnished to the Representatives a certificate of the Company, signed by the Chairman of the Board or the Chief Executive
Officer and the principal financial or accounting officer of the Company, dated the Closing Date, to the effect that the signers of such certificate have carefully examined the Registration Statement, the Final Prospectus, the Disclosure Package and
any supplements or amendments thereto and this Agreement and that: 
 (i) the representations and warranties of the Company in this Agreement
are true and correct in all material respects on and as of the Closing Date with the same effect as if made on the Closing Date, provided, however, that if any such representation or warranty is already qualified by materiality, such
representation or warranty as so qualified is true and correct in all respects on and as of the Closing Date, and the Company has complied with all the agreements and satisfied all the conditions on its part to be performed or satisfied at or prior
to the Closing Date; 
  

 10 

 (ii) no stop order suspending the effectiveness of the Registration Statement has been issued and no
proceedings for that purpose have been instituted or, to the Company’s knowledge, threatened; and 
 (iii) since the date of the most
recent financial statements included or incorporated by reference in the Final Prospectus (exclusive of any supplement thereto), there has been no Material Adverse Effect, except as set forth in or contemplated in the Disclosure Package and the
Final Prospectus (exclusive of any supplement thereto). 
 (f) The Company shall have requested and caused Deloitte & Touche LLP to
have furnished to the Representatives, at the Execution Time and at the Closing Date, letters, dated respectively as of the Execution Time and as of the Closing Date, in form and substance satisfactory to the Representatives, confirming that they
are independent registered public accountants with respect to the Company within the meaning of the Act and the Exchange Act and the respective applicable rules and regulations adopted by the Commission thereunder, and stating in effect that:

 (i) in their opinion the audited financial statements and financial statement schedules included or incorporated by reference in the
Registration Statement, the Disclosure Package and the Final Prospectus and reported on by them comply as to form in all material respects with the applicable accounting requirements of the Act and the Exchange Act and the related rules and
regulations adopted by the Commission; 
 (ii) on the basis of a reading of the latest unaudited financial statements made available by the
Company and its subsidiaries; their limited review, in accordance with standards established under Statement on Auditing Standards No. 100, of the unaudited interim financial information for the six-month period ended June 30, 2006 and as
at June 30, 2006 carrying out certain specified procedures (but not an examination in accordance with generally accepted auditing standards) which would not necessarily reveal matters of significance with respect to the comments set forth in
such letter; a reading of the minutes of the meetings of the shareholders, directors and executive and audit committees of the Company and its significant subsidiaries; and inquiries of certain officials of the Company who have responsibility for
financial and accounting matters of the Company and its subsidiaries as to transactions and events subsequent to December 31, 2005, nothing came to their attention which caused them to believe that: 
 (1) any unaudited financial statements included or incorporated by reference in the Registration Statement and the Final Prospectus do not comply as to
form in all material respects with applicable accounting requirements of the Act and with the related rules and regulations adopted by the Commission with respect to financial statements included or incorporated by reference in quarterly reports on
Form 10-Q under the Exchange Act; and said unaudited financial statements are not in conformity with generally accepted accounting principles applied on a basis substantially consistent with that of the audited financial statements included or
incorporated by reference in the Registration Statement and the Final Prospectus; 
 (2) with respect to the period subsequent to
June 30, 2006, there were any changes, at a specified date not more than five days prior to the date of the letter, in the long-term debt of the Company and its subsidiaries or capital stock of the Company or decreases in the stockholders’
equity of the Company as compared with the corresponding amounts shown on the June 30, 2006 balance sheets included or incorporated by reference in the Registration Statement and the Final Prospectus, or for the period from July 1, 2006 to
such specified date there were any decreases, as compared with the corresponding period in the preceding year in net income of the Company and its subsidiaries or in operating income of the Company and its subsidiaries, in each case, on either a
total or per share basis, except in all instances for changes or decreases set forth in such letter, in which case the letter shall be accompanied by an explanation by the Company as to the significance thereof unless said explanation is not deemed
necessary by the 
  

 11 

 Representatives (except that, for any periods subsequent to June 30, 2006 for which there are
currently no consolidated financial statements of the Company, the statement shall instead be that nothing has come to their attention which caused them to believe that there have been any increases in the long-term debt of the Company and its
subsidiaries or capital stock of the Company since the Company’s last consolidated financial statement); 
 (3) the information included
or incorporated by reference in the Registration Statement and Final Prospectus in response to Regulation S-K, Item 301 (Selected Financial Data), Item 302 (Supplementary Financial Information) and Item 402 (Executive Compensation) is
not in conformity with the applicable disclosure requirements of Regulation S-K; 
 (iii) they have performed certain other specified
procedures as a result of which they determined that certain information of an accounting, financial or statistical nature (which is limited to accounting, financial or statistical information derived from the general accounting records of the
Company and its subsidiaries) set forth or incorporated by reference in the Registration Statement and the Final Prospectus and in Exhibit 12 to the Registration Statement agrees with the accounting records of the Company and its subsidiaries,
excluding any questions of legal interpretation. 
 References to the Final Prospectus in this paragraph (f) include any supplement
thereto at the date of the letter. 
 (g) Subsequent to the Execution Time or, if earlier, the dates as of which information is given in the
Registration Statement (exclusive of any amendment thereof) and the Final Prospectus (exclusive of any supplement thereto), there shall not have been (i) any change or decrease specified in the letter or letters referred to in paragraph
(f) of this Section 6 or (ii) any change, or any development involving a prospective change, in or affecting the financial condition, earnings, business or properties of the Company and its subsidiaries, taken as a whole, whether or
not arising from transactions in the ordinary course of business, except as set forth in or contemplated in the Disclosure Package the effect of which, in any case referred to in clause (i) or (ii) above, is, in the sole judgment of the
Representatives, so material and adverse as to make it impractical or inadvisable to proceed with the offering or delivery of the Securities as contemplated by the Registration Statement (exclusive of any amendment thereof) and the Disclosure
Package. 
 (h) Prior to the Closing Date, the Company shall have furnished to the Representatives such further information, certificates and
documents as the Representatives may reasonably request. 
 (i) Subsequent to the Execution Time, there shall not have been any decrease in
the rating of any of the Company’s debt securities by any “nationally recognized statistical rating organization” (as defined for purposes of Rule 436(g) under the Act) or any notice given of any intended or potential decrease in any
such rating or of a possible change in any such rating that does not indicate the direction of the possible change. 
 (j) Subject to official
notice of issuance, the Securities shall have been listed and admitted and authorized for trading on the New York Stock Exchange, and satisfactory evidence of such actions shall have been provided to the Representatives. 
 (k) At the Execution Time, the Company shall have furnished to the Representatives a letter substantially in the form of Exhibit C hereto from Loews
Corporation and each executive officer and director of the Company addressed to the Representatives. 
 If any of the conditions specified in
this Section 6 shall not have been fulfilled in all material respects when and as provided in this Agreement, or if any of the opinions and certificates mentioned above or elsewhere in this Agreement shall not be in all material respects
reasonably satisfactory in form and substance to the 
  

 12 

 Representatives and counsel for the Underwriters, this Agreement and all obligations of the Underwriters
hereunder may be canceled at, or at any time prior to, the Closing Date by the Representatives. Notice of such cancellation shall be given to the Company in writing or by telephone or facsimile confirmed in writing. 
 The documents required to be delivered by this Section 6 shall be delivered at the offices of Mayer, Brown, Rowe & Maw LLP, counsel for the
Company, at 71 South Wacker Drive, Chicago, Illinois 60606, on the Closing Date. 
 7. Reimbursement of Underwriters’ Expenses. If the sale of
the Securities provided for herein is not consummated because any condition to the obligations of the Underwriters set forth in Section 6 hereof is not satisfied, because of any termination pursuant to Section 10(i) hereof or because of
any refusal, inability or failure on the part of the Company to perform any agreement herein or comply with any provision hereof other than by reason of a default by any of the Underwriters, the Company will reimburse the Underwriters severally
through the Representatives on demand for all reasonable out-of-pocket expenses (including reasonable fees and disbursements of counsel) that shall have been incurred by them solely and directly in connection with the proposed purchase and sale of
the Securities. 
 8. Indemnification and Contribution. (a) The Company agrees to indemnify and hold harmless each Underwriter, the
directors, officers, employees and agents of each Underwriter and each person who controls any Underwriter within the meaning of either the Act or the Exchange Act against any and all losses, claims, damages or liabilities, joint or several, to
which they or any of them may become subject under the Act, the Exchange Act or other Federal or state statutory law or regulation, at common law or otherwise, insofar as such losses, claims, damages or liabilities (or actions in respect thereof)
arise out of or are based upon any untrue statement or alleged untrue statement of a material fact contained in the registration statement for the registration of the Securities as originally filed or in any amendment thereof, or in the Basic
Prospectus, any Preliminary Final Prospectus, the Final Prospectus, any Issuer Free Writing Prospectus, the Disclosure Package or in any amendment thereof or supplement thereto, or arise out of or are based upon the omission or alleged omission to
state therein a material fact required to be stated therein or necessary to make the statements therein not misleading, and agrees to reimburse each such indemnified party, as incurred, for any legal or other expenses reasonably incurred by them in
connection with investigating or defending any such loss, claim, damage, liability or action; provided, however, that the Company will not be liable in any such case to the extent that any such loss, claim, damage or liability arises
out of or is based upon any such untrue statement or alleged untrue statement or omission or alleged omission made therein in reliance upon and in conformity with written information furnished to the Company by or on behalf of any Underwriter
through the Representatives specifically for inclusion therein. This indemnity agreement will be in addition to any liability which the Company may otherwise have. 
 (b) Each Underwriter severally and not jointly agrees to indemnify and hold harmless the Company, each of its directors, each of its officers who signs the Registration Statement, and each person who controls the
Company within the meaning of either the Act or the Exchange Act, to the same extent as the foregoing indemnity from the Company to each Underwriter, but only with reference to written information relating to such Underwriter furnished to the
Company by or on behalf of such Underwriter through the Representatives specifically for inclusion in the documents referred to in the foregoing indemnity. This indemnity agreement will be in addition to any liability which any Underwriter may
otherwise have. The Company acknowledges that the statements set forth on Schedule I hereto under the caption “Information provided for purposes of Section 8(b)” constitute the only information furnished in writing by or on behalf of
the several Underwriters for inclusion in any Preliminary Final Prospectus, the Final Prospectus, any Issuer Free Writing Prospectus or the Disclosure Package. 
 (c) Promptly after receipt by an indemnified party under this Section 8 of notice of the commencement of any action, such indemnified party will, if a claim in respect thereof is to be made against the
indemnifying party under this Section 8, notify the indemnifying party in writing of the commencement thereof; but the failure so to notify the indemnifying party (i) will not relieve it from liability under paragraph (a) or
(b) above unless and to the extent it did not otherwise learn of such action and such failure results in the forfeiture by the indemnifying party of substantial rights and defenses and (ii)
  

 13 

 will not, in any event, relieve the indemnifying party from any obligations to any indemnified party
other than the indemnification obligation provided in paragraph (a) or (b) above. The indemnifying party shall be entitled to appoint counsel of the indemnifying party’s choice at the indemnifying party’s expense to represent the
indemnified party in any action for which indemnification is sought (in which case the indemnifying party shall not thereafter be responsible for the fees and expenses of any separate counsel retained by the indemnified party or parties except as
set forth below); provided, however, that such counsel shall be reasonably satisfactory to the indemnified party. Notwithstanding the indemnifying party’s election to appoint counsel to represent the indemnified party in an
action, the indemnified party shall have the right to employ separate counsel (including local counsel), and the indemnifying party shall bear the reasonable fees, costs and expenses of such separate counsel if (i) the use of counsel chosen by
the indemnifying party to represent the indemnified party would present such counsel with a conflict of interest, (ii) the actual or potential defendants in, or targets of, any such action include both the indemnified party and the indemnifying
party and the indemnified party shall have reasonably concluded that there may be legal defenses available to it and/or other indemnified parties which are different from or additional to those available to the indemnifying party, (iii) the
indemnifying party shall not have employed counsel reasonably satisfactory to the indemnified party to represent the indemnified party within a reasonable time after notice of the institution of such action or (iv) the indemnifying party shall
authorize the indemnified party to employ separate counsel at the expense of the indemnifying party. An indemnifying party will not, without the prior written consent of the indemnified parties, settle or compromise or consent to the entry of any
judgment with respect to any pending or threatened claim, action, suit or proceeding in respect of which indemnification or contribution may be sought hereunder (whether or not the indemnified parties are actual or potential parties to such claim or
action) unless such settlement, compromise or consent includes an unconditional release of each indemnified party from all liability arising out of such claim, action, suit or proceeding. 
 (d) In the event that the indemnity provided in paragraph (a) or (b) of this Section 8 is unavailable to or insufficient to hold harmless
an indemnified party for any reason, the Company and the Underwriters severally agree to contribute to the aggregate losses, claims, damages and liabilities (including legal or other expenses reasonably incurred in connection with investigating or
defending same) (collectively “Losses”) to which the Company and one or more of the Underwriters may be subject in such proportion as is appropriate to reflect the relative benefits received by the Company on the one hand and by the
Underwriters on the other from the offering of the Securities; provided, however, that in no case shall any Underwriter (except as may be provided in any agreement among underwriters relating to the offering of the Securities) be
responsible for any amount in excess of the underwriting discount or commission applicable to the Securities purchased by such Underwriter hereunder. If the allocation provided by the immediately preceding sentence is unavailable for any reason, the
Company and the Underwriters severally shall contribute in such proportion as is appropriate to reflect not only such relative benefits but also the relative fault of the Company on the one hand and of the Underwriters on the other in connection
with the statements or omissions which resulted in such Losses as well as any other relevant equitable considerations. Benefits received by the Company shall be deemed to be equal to the total net proceeds from the offering (before deducting
expenses) received by the Company, and benefits received by the Underwriters shall be deemed to be equal to the total underwriting discounts and commissions, in each case as set forth on the cover page of the Final Prospectus. Relative fault shall
be determined by reference to, among other things, whether any untrue or any alleged untrue statement of a material fact or the omission or alleged omission to state a material fact relates to information provided by the Company on the one hand or
the Underwriters on the other, the intent of the parties and their relative knowledge, access to information and opportunity to correct or prevent such untrue statement or omission. The Company and the Underwriters agree that it would not be just
and equitable if contribution were determined by pro rata allocation or any other method of allocation which does not take account of the equitable considerations referred to above. Notwithstanding the provisions of this paragraph (d), no person
guilty of fraudulent misrepresentation (within the meaning of Section 11(f) of the Act) shall be entitled to contribution from any person who was not guilty of such fraudulent misrepresentation. For purposes of this Section 8, each person
who controls an Underwriter within the meaning of either the Act or the Exchange Act and each director, officer, employee and agent of an Underwriter shall have the same rights to contribution as such Underwriter, and each person who controls the
Company within the meaning of either the Act or the Exchange Act, each officer of the Company who shall have signed the Registration Statement and each director of the Company shall have the same rights to contribution as the Company, subject in
each case to the applicable terms and conditions of this paragraph (d). 
  

 14 

 9. Default by an Underwriter. If any one or more Underwriters shall fail to purchase and pay for any of the
Securities agreed to be purchased by such Underwriter or Underwriters hereunder and such failure to purchase shall constitute a default in the performance of its or their obligations under this Agreement, the remaining Underwriters shall be
obligated severally to take up and pay for (in the respective proportions which the amount of Securities set forth opposite their names in Schedule II hereto bears to the aggregate amount of Securities set forth opposite the names of all the
remaining Underwriters) the Securities which the defaulting Underwriter or Underwriters agreed but failed to purchase; provided, however, that in the event that the aggregate amount of Securities which the defaulting Underwriter or
Underwriters agreed but failed to purchase shall exceed 10% of the aggregate amount of Securities set forth in Schedule II hereto, the remaining Underwriters shall have the right to purchase all, but shall not be under any obligation to purchase
any, of the Securities, and if such nondefaulting Underwriters do not purchase all the Securities, this Agreement will terminate without liability to any nondefaulting Underwriter or the Company. In the event of a default by any Underwriter as set
forth in this Section 9, the Closing Date shall be postponed for such period, not exceeding five Business Days, as the Representatives shall determine in order that the required changes in the Registration Statement and the Final Prospectus or
in any other documents or arrangements may be effected. Nothing contained in this Agreement shall relieve any defaulting Underwriter of its liability, if any, to the Company and any nondefaulting Underwriter for damages occasioned by its default
hereunder. 
 10. Termination. This Agreement shall be subject to termination in the absolute discretion of the Representatives, by notice given to
the Company prior to delivery of and payment for the Securities, if at any time after the execution of this Agreement and prior to such time (i) trading in any securities of the Company shall have been suspended by the Commission or the New
York Stock Exchange (other than a suspension covered by clause (ii)), (ii) trading in securities generally on the New York Stock Exchange or the Nasdaq National Market shall have been suspended or limited or minimum prices shall have been
established on such Exchange or the Nasdaq National Market, (iii) a banking moratorium shall have been declared either by Federal or New York State authorities or (iv) there shall have occurred any outbreak or escalation of hostilities,
declaration by the United States of a national emergency or war, or other calamity or crisis the effect of which on financial markets is such as to make it, in the sole judgment of the Representatives, impractical or inadvisable to proceed with the
offering or delivery of the Securities as contemplated by the Final Prospectus (exclusive of any supplement thereto). 
 11. Representations and
Indemnities to Survive. The respective agreements, representations, warranties, indemnities and other statements of the Company or its officers and of the Underwriters set forth in or made pursuant to this Agreement will remain in full force and
effect, regardless of any investigation made by or on behalf of any Underwriter or the Company or any of the officers, directors, employees, agents or controlling persons referred to in Section 8 hereof, and will survive delivery of and payment
for the Securities. The provisions of Sections 7 and 8 hereof shall survive the termination or cancellation of this Agreement. 
 12. Notices. All
communications hereunder will be in writing and effective only on receipt, and, if sent to the Representatives, will be mailed, delivered or telefaxed to the Representatives at the address set forth in Schedule I hereto; or, if sent to the Company,
will be mailed, delivered or telefaxed to the General Counsel, CNA Financial Corporation (fax no.: (312) 822-1297) and confirmed to it in writing at CNA Financial Corporation, 333 South Wabash Avenue, Chicago, Illinois 60604, Attention: General
Counsel. 
 13. Successors. This Agreement will inure to the benefit of and be binding upon the parties hereto and their respective successors and the
officers, directors, employees, agents and controlling persons referred to in Section 8 hereof, and no other person will have any right or obligation hereunder. 
 14. Applicable Law. This Agreement will be governed by and construed in accordance with the laws of the State of New York applicable to contracts made and to be performed within the State of New York.

 15. Counterparts. This Agreement may be signed in one or more counterparts, each of which shall constitute an original and all of which together
shall constitute one and the same agreement. 
  

 15 

 16. Headings. The section headings used herein are for convenience only and shall not affect the construction
hereof. 
 17. Arms-length Transaction. The Company and the Underwriters acknowledge and agree that (i) the purchase and sale of the Securities
pursuant to this Agreement is an arm’s-length commercial transaction between the Company, on the one hand, and the Underwriters, on the other, (ii) in connection therewith and with the process leading to such transaction each Underwriter
is acting solely as a principal and not the agent or fiduciary of the Company, (iii) no Underwriter has assumed an advisory or fiduciary responsibility in favor of the Company with respect to the offering contemplated hereby or the process
leading thereto (irrespective of whether such Underwriter has advised or is currently advising the Company on other matters) or any other obligation to the Company except the obligations expressly set forth in this Agreement and (iv) each of
the Company and the Underwriters has consulted its own legal and financial advisors to the extent it deemed appropriate. The Company agrees that it will not claim that the Underwriters, or any of them, has rendered advisory services of any nature or
respect, or owes a fiduciary or similar duty to them, in connection with such transaction or the process leading thereto. 
 18. Integration. This
Agreement supersedes all prior agreements and understandings (whether written or oral) between the Company and the Underwriters, or any of them, with respect to the subject matter hereof. 
 19. Waiver of Jury Trial. The Company and each of the Underwriters hereby irrevocably waives, to the fullest extent permitted by applicable law, any and all right
to trial by jury in any legal proceeding arising out of or relating to this Agreement or the transactions contemplated hereby. 
  

	20.	Definitions. The terms which follow, when used in this Agreement, shall have the meanings indicated. 

 “Act” shall mean the Securities Act of 1933, as amended, and the rules and regulations of the Commission promulgated thereunder. 
 “Applicable Time” shall mean 5:51 pm (Eastern time) on the date of this Agreement. 
 “Basic Prospectus” shall mean the prospectus referred to in paragraph 1(a) above contained in the Registration Statement at the Effective Date,
including any documents incorporated by reference therein. 
 “Business Day” shall mean any day other than a Saturday, a Sunday or a
legal holiday or a day on which banking institutions or trust companies are authorized or obligated by law to close in New York City. 
 “Commission” shall mean the Securities and Exchange Commission. 
 “Disclosure Package” shall mean (i) the
Basic Prospectus, as amended and supplemented to the Applicable Time, (ii) the other information, if any, identified in Schedule IV hereto, (iii) Issuer Free Writing Prospectuses, if any, identified in Schedule III hereto, and
(iv) any other Free Writing Prospectus that the parties hereto shall hereafter expressly agree in writing to treat as part of the Disclosure Package. 
 “Effective Date” shall mean each date and time that the Registration Statement, any post-effective amendment or amendments thereto became or become effective. 
 “Exchange Act” shall mean the Securities Exchange Act of 1934, as amended, and the rules and regulations of the Commission promulgated
thereunder. 
 “Execution Time” shall mean the date and time that this Agreement is executed and delivered by the parties hereto.

 “Final Prospectus” shall mean the prospectus supplement relating to the Securities that was first filed pursuant to Rule 424(b)
after the Execution Time, together with the Basic Prospectus. 
 “Free Writing Prospectus” shall mean a free writing prospectus, as
defined in Rule 405. 
  

 16 

 “Issuer Free Writing Prospectus” shall mean an issuer free writing prospectus, as defined in
Rule 433. 
 “Material Adverse Effect” shall mean a material adverse effect on the financial condition, earnings, business or
properties of the Company and its subsidiaries, taken as a whole, whether or not arising from transactions in the ordinary course of business. 
 “Material Subsidiaries” shall mean CNA Surety Corporation, Continental Assurance Company, Continental Casualty Company, Firemen’s Insurance Company of Newark, New Jersey, The Buckeye Union Insurance Company, The Continental
Insurance Company, The Glens Falls Insurance Company and The Continental Corporation. 
 “Preliminary Final Prospectus” shall mean
any preliminary prospectus supplement to the Basic Prospectus which describes the Securities and the offering thereof and is used prior to filing of the Final Prospectus, including any documents incorporated by reference therein, together with the
Basic Prospectus. 
 “Registration Statement” shall mean the registration statement referred to in paragraph 1(a) above, including
exhibits, financial statements and any documents incorporated by reference therein and any prospectus supplement relating to the Securities that is filed with the Commission pursuant to Rule 424(b) and deemed part of such registration statement
pursuant to Rule 430B, as amended at the Execution Time and, in the event any post-effective amendment thereto becomes effective prior to the Closing Date, shall also mean such registration statement as so amended. 
 “Rule 158”, “Rule 163”, “Rule 164”, “Rule 172”, “Rule 405”, “Rule 415”,
“Rule 424”, “Rule 430B”, and “Rule 433” refer to such rules under the Act. 
  

 17 

 If the foregoing is in accordance with your understanding of our agreement, please sign and return to us
the enclosed duplicate hereof, whereupon this letter and your acceptance shall represent a binding agreement among the Company and the several Underwriters. 
  

			
	CNA Financial Corporation
		
	By:	 	 /s/ D. Craig Mense

	Name:	 	D. Craig Mense
	Title:	 	 Executive Vice President
 and Chief Financial
Officer

 The foregoing Agreement is hereby 
 confirmed and accepted as of the 
 date first above written. 
  

			
	By:	 	Citigroup Global Markets Inc.
		
	By:	 	 /s/ Jack D. McSpadden, Jr.

	Name:	 	Jack D. McSpadden, Jr.
	Title:	 	Managing Director

 For themselves and the other 
 several Underwriters named in 
 Schedule II to the foregoing 
 Agreement. 
 [Signature Page to the Underwriting Agreement] 
  

 18 

 EXHIBIT A 
 Opinion of Mayer, Brown, Rowe & Maw LLP 
 August 4, 2006 
 Citigroup 
 [Underwriter name and address]

 Re: Public Offering of CNA Financial Corporation common stock, par value $2.50 per share 
 Ladies and Gentlemen: 
 This opinion is furnished to the
several underwriters named in Schedule II to the Underwriting Agreement (as defined below) (the “Underwriters”), at the request of the CNA Financial Corporation, a Delaware corporation (the “Company”), in connection with the
Underwriting Agreement, dated August 1, 2006 (the “Underwriting Agreement”), between the Underwriters and the Company, pursuant to which the Underwriters have agreed to purchase for public offering an aggregate of 7,000,000 shares of
common stock, par value $2.50 per share, of the Company (the “Securities”). Capitalized terms used herein which are not defined in this opinion shall have the meanings ascribed to them in the Underwriting Agreement. 
 We have acted as special counsel to the Company in connection with the purchase by the Underwriters for public offering of the Securities. In that
connection we have examined such documents, certificates, corporate records, opinions and other instruments and have made such examinations of law as we have deemed necessary or appropriate for the purpose of this opinion. In making such
examination, we have assumed the genuineness of all signatures, the authenticity of all documents submitted to us as originals, and the conformity to authentic, original documents of all documents submitted to us as certified, conformed or
photostatic copies. As to questions of fact (but not as to matters of law) material to such opinions, we have, when relevant facts were not independently established by us, relied upon representations, warranties and covenants contained in the
Underwriting Agreement, statements made in the Final Prospectus and upon statements made in the documents, records, certificates and resolutions referred to above. We have assumed the due execution and delivery by you, pursuant to due authorization,
of the Underwriting Agreement. We have also participated on behalf of the Company in the preparation of the Registration Statement and the Final Prospectus. 
 On the basis of the foregoing and subject to the qualifications set forth below, it is our opinion that: 
 1. The Company is validly existing in good standing under the laws of the State of Delaware. The Company has the corporate power and corporate authority to carry on its business and to own, lease and operate its properties, in each
case as described in the Disclosure Package and the Final Prospectus. 
 2. The Company has an authorized capitalization as set forth in
the Disclosure Package and the Final Prospectus, and the authorized capital stock of the Company conforms as to legal matters to the description thereof contained in the Disclosure Package and the Final Prospectus. 
 3. The Securities have been duly authorized by the Company and, when delivered to and paid for by you in accordance with the terms of the Underwriting
Agreement, will be validly issued, fully paid and nonassessable. 
  

 19 

 4. The Securities have been authorized for listing on the NYSE, subject to official notice of issuance.

 5. The Specimen Certificate complies in all material respects with the applicable requirements of the Certificate of Incorporation
and By-laws, the DGCL and the New York Stock Exchange. 
 6. The holders of outstanding shares of capital stock of the Company do not
have any preemptive rights or any similar rights arising under the Certificate of Incorporation, the By-laws or the DGCL to subscribe for the Securities as a result of the transactions contemplated by the Underwriting Agreement. 
 7. The statements in the Base Prospectus under the headings “Description of Common Stock,” insofar as such statements purport to summarize
certain provisions of the Certificate of Incorporation, the By-laws and the DGCL, fairly summarize such provisions in all material respects. 
 8. The Underwriting Agreement has been duly authorized, executed and delivered by the Company. 
 9. The Company is
not, and after giving effect to the offering and sale of the Securities and the application of the proceeds thereof as described in the Final Prospectus, will not be subject to registration and regulation as an “investment company” as such
term is defined in the Investment Company Act of 1940, as amended.
 10. The Registration Statement and any amendments
thereto have become effective under the Securities Act; to our knowledge, no stop order suspending the effectiveness of the Registration Statement, as amended, has been issued, no proceedings for that purpose have been instituted or threatened, and
the Registration Statement, the Final Prospectus and each amendment thereof or supplement thereto as of their respective effective or issue dates (other than the financial statements and other financial information contained therein, as to which we
express no opinion) complied as to form in all material respects with the applicable requirements of the Securities Act and the Exchange Act and the respective rules and regulations thereunder.
 11. The Registration Statement and the Final Prospectus (except for the financial statements and financial schedules and other financial data
included therein, as to which we do not express any opinion) appear on their face to be appropriately responsive in all material respects with the requirements of the Securities Act and the applicable rules and regulations of the Commission
thereunder. 
 Our opinion set forth in paragraph 1 above with respect to the valid existence and good standing of the Company is based
solely upon a certificate of the Secretary of State of the State of Delaware delivered to you in connection with the closing of the transactions contemplated by the Underwriting Agreement. 
 We are admitted to practice law in the States of Illinois and New York and our opinions expressed herein are limited solely to the federal laws of the
United States of America and the laws of the States of New York and the Delaware General Corporation Law, and we express no opinion herein concerning the laws of any other jurisdiction. 
 We are not passing upon and assume no responsibility for the accuracy, completeness or fairness of the statements contained in the Registration Statement
or any amendments thereto, the Final Prospectus or the Disclosure Package nor, except as set forth in paragraphs 2 and 7 above, are we making any representation that we have independently verified or checked the accuracy, completeness or fairness of
such statements. Also, we are expressing no view as to the financial statements and related schedules or the other financial data included or incorporated by reference in the Registration Statement, the Final Prospectus or the Disclosure Package or
omitted therefrom. However, as indicated above, we examined various documents and records and participated in conferences with your representatives, representatives of the Company, the Company’s counsel and the Company’s auditors, at which
time the contents of the Registration Statement, the Final Prospectus, the Disclosure Package and related matters were discussed. Subject to the foregoing, we advise you that no facts have come to our attention as a result of the foregoing which
have caused us to believe that (i) at the Effective Date immediately preceding the Execution Time, the Registration Statement contained any untrue statement of a material fact or omitted to state any 
  

 20 

 material fact required to be stated therein or necessary to make the statements therein not misleading, (ii) the
Disclosure Package, as of the Applicable Time, included any untrue statement of a material fact or omitted to state a material fact necessary to make the statements therein, in the light of the circumstances under which they were made, not
misleading or (iii) the Final Prospectus as of its date and as of the Closing Date includes any untrue statement of a material fact or omits to state a material fact necessary to make the statements therein, in the light of the circumstances
under which they were made, not misleading. 
 The opinions and statements expressed herein are as of the date hereof. We assume no
obligation to update or supplement this opinion letter to reflect any facts or circumstances that may hereafter come to our attention or any changes in applicable law that may hereafter occur. 
 This letter is furnished by us pursuant to Section 6(b) of the Underwriting Agreement and is solely for your benefit and may not be relied upon by
any other party (including any person purchasing Securities through an Underwriter) without our express written consent. 
 Very truly yours,

  

 21 

 EXHIBIT B 
 [Letterhead of CNA Financial Corp] 
 August 4, 2006 
 Citigroup 
 [Underwriter name and address] 
 Re: Public Offering of CNA Financial Corporation common stock, par value $2.50 per share

 Ladies and Gentlemen: 
 I am providing this
opinion as Executive Vice President, General Counsel and Secretary of CNA Financial Corporation, a Delaware corporation (the “Company”), in connection with the issuance and sale by the Company to the several underwriters named in Schedule
II of the hereinafter defined Underwriting Agreement (the “Underwriters”), of 7,000,000 shares of common stock (the “Securities”), par value $2.50 per share of the Company (the “Common Stock”), pursuant to the
Underwriting Agreement, dated as of August 1,2006, between the Company and the Underwriters (the “Underwriting Agreement”). Capitalized terms used but not defined herein are used as defined in the Underwriting Agreement. 

In that connection, I, or attorneys under my supervision, have reviewed and examined: (i) the Registration Statement; (ii) the Disclosure
Package, (iii) the Basic Prospectus; (iv) the Final Prospectus; (v) the Certificate of Incorporation of the Company, as amended through the date hereof; (vi) the By-laws of the Company, as amended through the date hereof;
(vii) a specimen certificate representing the Securities; and (viii) the resolutions of the Board of Directors of the Company relating to the issuance of the Securities. In addition, I have reviewed such other documents and
instruments, investigated such matters of law, and as to matters of fact, to the extent I have deemed proper, relied on certificates of responsible officers of the Company and certificates or other written statements of officials of jurisdictions
having custody of documents with respect to the corporate existence or good standing of the Company, conferred with such officers and directors of the Company and the Material Subsidiaries, and ascertained or verified to my satisfaction such
additional facts with respect to the Company which I have deemed necessary or appropriate for the purposes of this opinion. I have with your consent also assumed the legal capacity of all natural persons, the genuineness of all signatures, the
authenticity of all documents submitted to me as originals and the conformity to original documents of all documents submitted to me as copies. 
 I am a member of the Bar of the State of New York and of Illinois and do not express any opinion as to any matters governed by any laws other than the laws of New York and Illinois, the General Corporation Law of the State of Delaware and
the federal laws of the United States. 
 (i) the Company is validly existing as a corporation in good standing under the laws the State of Delaware,
with full corporate power and authority to own or lease, as the case may be, and to operate its properties and conduct its business as described in the Disclosure Package and the Final Prospectus, and is duly qualified to do business as a foreign
corporation and is in good standing under the laws of each jurisdiction which requires such qualification, except where the failure to be so qualified could not, individually or in the aggregate, reasonably be expected to have a Material Adverse
Effect; 
 (ii) each of the Material Subsidiaries is validly existing as an insurance company (other than The Continental Corporation, which is validly
existing as a New York business corporation, and CNA Surety Corporation, which is validly existing as a Delaware corporation) and is authorized to transact its appropriate business under the insurance code of its domiciliary state, with full
corporate power and authority to own is properties and conduct its business as described in the Disclosure Package and the Final Prospectus, and is duly licensed to do business as a foreign insurer 
  

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 and is authorized to transact its appropriate business under the laws of each jurisdiction which requires such licensure
wherein it owns or leases material properties or conducts material business where the failure to be so licensed could not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect; 
 (iii) all the outstanding shares of capital stock of each Material Subsidiary have been duly and validly authorized and issued and are fully paid and nonassessable,
and, except to the extent otherwise set forth in the Disclosure Package and the Final Prospectus, all outstanding shares of capital stock of the Material Subsidiaries are owned by the Company either directly or through wholly owned subsidiaries
(except for CNA Surety Corporation, of which the Company owns approximately 63%) free and clear of any perfected security interest and, to my knowledge, after due inquiry, any other security interest, claim, lien or encumbrance; 
 (iv) except as set forth in the Disclosure Package and the Final Prospectus, to my knowledge, no options, warrants, preemptive rights or other rights to purchase
from the Company, agreements or other obligations of the Company to issue, or rights to require the Company to convert any obligations into or exchange any securities for, shares of the Common Stock are outstanding; 
 (v) to my knowledge, there is no pending or threatened action, suit or proceeding by or before any court or governmental agency, authority or body or any arbitrator
involving the Company or any of its subsidiaries or its or their property of a character required to be disclosed in the Registration Statement which is not adequately disclosed in the Disclosure Package and the Final Prospectus, and there is no
franchise, contract or other document of a character required to be described in the Registration Statement or Final Prospectus, or to be filed as an exhibit thereto, which is not described or filed as required. 
 (vi) neither the issue and sale of the Securities, nor the consummation of any other of the transactions contemplated by the Underwriting Agreement, nor the
fulfillment of the terms of the Underwriting Agreement will conflict with, result in a breach or violation of, or the imposition of any lien, charge or encumbrance upon any property or assets of the Company or its Material Subsidiaries pursuant to,
(i) the charter or by-laws of the Company or of its Material Subsidiaries that are corporations or the certificate of formation or operating agreement of any Material Subsidiary that is a limited partnership, (ii) the terms of any
indenture, contract, lease, mortgage, deed of trust, note agreement, loan agreement or other agreement, obligation, condition, covenant or instrument to which the Company or any of its Material Subsidiaries is a party or bound or to which its or
their property is subject, or (iii) any statute, law, rule, regulation, judgment, order or decree applicable to the Company or its Material Subsidiaries of any court, regulatory body, administrative agency, governmental body, arbitrator or
other authority having jurisdiction over the Company or its Material Subsidiaries or any of its or their properties, except, with respect to clauses (ii) and (iii) above, for such conflicts, breaches, violations or impositions that could
not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect; 
 (vii) to my knowledge, no holders of securities of
the Company have rights to the registration of such securities under the Registration Statement; and 
 (ix) no consent, approval, authorization, filing
with or order of any court or governmental agency or body is required in connection with the performance by the Company of its obligations under the Underwriting Agreement, except such as have been obtained under the Act and such as may be required
to be obtained by the Company under the blue sky laws of any jurisdiction in connection with the purchase from the Company and distribution of the Shares by the Underwriter in the manner contemplated in the Underwriting Agreement and in the Final
Prospectus and such other approvals as have been obtained. 
 I am not passing upon and assume no responsibility for the accuracy,
completeness or fairness of the statements contained in the Registration Statement or any amendments thereto, the Final Prospectus or the Disclosure Package nor am I making any representation that I have independently verified or checked the
accuracy, completeness or fairness of such statements. Also, I am not expressing any view as to the financial statements and related schedules or the other financial data included or incorporated by reference in the Registration Statement, the Final
Prospectus or the Disclosure Package or omitted therefrom. However, as indicated above, I or attorneys under my supervision have examined various documents and records and participated in conferences with your 
  

 23 

 representatives, representatives of the Company, the Company’s counsel and the Company’s auditors, at which
time the contents of the Registration Statement, the Final Prospectus, the Disclosure Package and related matters were discussed. Subject to the foregoing, I advise you that no facts have come to my attention as a result of the foregoing which have
caused me to believe that (i) at the Effective Date immediately preceding the Execution Time, the Registration Statement contained any untrue statement of a material fact or omitted to state any material fact required to be stated therein or
necessary to make the statements therein not misleading, (ii) the Disclosure Package, as of the Applicable Time, included any untrue statement of a material fact or omitted to state a material fact necessary to make the statements therein, in
the light of the circumstances under which they were made, not misleading or (iii) the Final Prospectus as of its date and as of the Closing Date includes any untrue statement of a material fact or omits to state a material fact necessary to
make the statements therein, in the light of the circumstances under which they were made, not misleading. 
 I do not purport herein to
cover the application of state blue sky or securities laws to the sale of the Common Stock. 
 The opinions and statements expressed herein
are as of the date hereof. I assume no obligation to update or supplement this opinion letter to reflect any facts or circumstances that may hereafter come to my attention or any changes in applicable law that may hereafter occur. 
 This opinion is rendered only to you and solely for your benefit in connection with the above transaction. This opinion may not be relied upon by you for
any other purpose, or relied upon by any other person, entity, firm or corporation (including purchases of Common Stock through the Underwriters) for any purpose without my prior written consent. The opinions contained herein are limited to the
matters expressly stated herein, and no opinion may be inferred or implied beyond the matters expressly stated herein. 
  

	
	Yours truly,
	
	Jonathan D. Kantor
	Executive Vice President, General Counsel and Secretary

  

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 EXHIBIT C 
 Form of Lock-up Agreement 
 [Letterhead of Loews Corporation 
 or officer or director of CNA Financial Corporation] 
 CNA Financial Corporation 
 Public Offering of Common Stock 
 August 1, 2006 
 To the Representatives named in Schedule I 
 to the Underwriting Agreement referenced 
 below (the “Representatives”), as 
 Representatives of the several Underwriters

 Ladies and Gentlemen: 
 This letter is being delivered to you
in connection with the proposed Underwriting Agreement (the “Underwriting Agreement”), between CNA Financial Corporation, a Delaware corporation (the “Company”), and each of you as representatives of a group of Underwriters named
therein, relating to an underwritten public offering of common stock, $2.50 par value per share (“Common Stock”), of the Company. 
 In order to
induce you and the other Underwriters to enter into the Underwriting Agreement, the undersigned will not, without the prior written consent of Representatives, offer, sell, contract to sell, pledge or otherwise dispose of (or enter into any
transaction which is designed to, or might reasonably be expected to, result in the disposition (whether by actual disposition or effective economic disposition due to cash settlement or otherwise) by the undersigned or any affiliate of the
undersigned or any person in privity with the undersigned or any affiliate of the undersigned), directly or indirectly, including the filing (or participation in the filing) of a registration statement with the Securities and Exchange Commission in
respect of, or establish or increase a put equivalent position or liquidate or decrease a call equivalent position within the meaning of Section 16 of the Securities Exchange Act of 1934, as amended, and the rules and regulations of the
Securities and Exchange Commission promulgated thereunder with respect to, any shares of Common Stock or any securities convertible into or exercisable or exchangeable for Common Stock, or publicly announce an intention to effect any such
transaction, for a period of 90 days after the date of the Underwriting Agreement, other than shares of Common Stock disposed of as bona fide gifts. 
 If
for any reason the Underwriting Agreement shall be terminated prior to the Closing Date (as defined in the Underwriting Agreement), the agreement set forth above shall likewise be terminated. 
 Yours very truly, 
  

 25 

 SCHEDULE I 
 Underwriting Agreement dated August 1, 2006. 
 Registration Statement No. 333-127544. 
 Representative(s): Citigroup Global Markets Inc. 
 Title, Purchase Price and
Description of Securities: 
 Title: CNA Financial Common Stock 
 Number of Securities to be sold by CNA: 7,000,000 
 Price per Share to the Underwriters - total: $33.64 
 Other provisions: 
 Closing Date, Time and Location: August 4, 2006 at 10:00 a.m. at the offices of Mayer, Brown, Rowe & Maw LLP, 71 South Wacker Drive, Chicago, Illinois 60606. 
 Information provided for purposes of Section 8(b): 
 (i) the last paragraph on the cover page of the Final Prospectus regarding sales by the Underwriters of the Securities and (ii) in the Final Prospectus under the heading “Underwriting,” (a) the
language in the first paragraph regarding the Underwriters and their respective participation in the sale of the Securities; (b) the third paragraph regarding sales by the Underwriters of the Securities; and (c) the seventh and eighth
paragraphs related to stabilization and syndicate covering transactions. 
 Address for notices pursuant to Section 12:

 Citigroup Global Markets Inc. 
 388 Greenwich Street

 New York, New York 10013 
 fax no.: (212) 816-7912

 Attention: General Counsel 
  

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 SCHEDULE II 
  

			
	 Underwriters
	  	 Number of
 Securities to be Purchased

	 Citigroup Global Markets Inc.
	  	7,000,000
		  	 
	 Total
	  	7,000,000
		  	 

  

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 SCHEDULE III 
 Schedule of Free Writing Prospectuses included in the Disclosure Package 
 None. 
  

 28 

 SCHEDULE IV 
 Schedule of other information included in the Disclosure Package 
  

			
	Issuer:	 	CNA Financial Corporation
		
	Underwriters:	 	Citigroup Global Markets Inc.
		
	Number of shares to be sold to the Underwriters:	 	7,000,000
		
	Price per share to the Underwriters:	 	$33.64
		
	Number of shares to be sold to Loews Corporation:	 	7,863,258

 Shares are subject to variable price reoffer by the Underwriters 
  

 29

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