Document:

EX-10.33

Exhibit 10.33

EMPLOYMENT AGREEMENT

(As amended and restated effective as of July 31, 2009)

     This Amended and Restated Employment Agreement (the “Agreement”) is effective as of
July 31, 2009 (the Effective Date”) by and between ODYSSEY RE HOLDINGS CORP. (“Employer”), a
holding company, incorporated in the State of Delaware, that owns all of the shares of the entities
comprising the group of reinsurance and insurance companies constituted by Odyssey America
Reinsurance Corporation and its subsidiaries, and Richard Scott Donovan (“Executive”).

WITNESSETH

     WHEREAS, Executive is the Chief Financial Officer of the Employer;

     WHEREAS, Executive entered into the Agreement effective as of August 15, 2006; and

     WHEREAS, the parties desire to amend and restate the Agreement as of the date hereof so as to
contain the terms and conditions set forth below and to govern the employment of Executive in the
capacity described in the first recital above.

NOW THEREFORE, IT IS AGREED AS FOLLOWS:

 

 

ARTICLE I

EMPLOYMENT AND DUTIES; COMPENSATION

Section 1:   Duties.

     During the term of this Agreement, Executive shall be employed by and shall serve Employer in
the capacity of Executive Vice President and Chief Financial Officer, and shall be employed by
and/or shall serve such subsidiaries of Employer in such capacities as Employer shall from time to
time designate and as are consistent with Executive’s position as Executive Vice President and
Chief Financial Officer of Employer. Executive shall devote substantially all of his business time
to the business and affairs of Employer and shall use his best efforts, skills, and energy to
promote Employer’s interests, provided that it shall not be a violation of the foregoing for
Executive to act or serve as a director, trustee or committee member of any civic or charitable
organization, as long as such activities are disclosed to Employer and Employer, in the exercise of
its reasonable judgment, agrees that such activities do not present any conflict of interest with
the Employer.

Section 2:   Term of Employment.

     The term of employment, hereunder, of Executive by Employer commenced as of August 15, 2006
(the “Commencement Date”) and shall continue until August 15, 2012 (the “Term”). At any time prior
to the expiration of the Term, Employer and Executive may, by mutual written agreement, extend
Executive’s employment under the terms of this Agreement for such additional periods as they may
agree.

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Section 3:   Salary, Benefits and Additional Compensation.

     As compensation and consideration for the performance by Executive of his duties and
responsibilities pursuant to this Agreement, Employer agrees to pay, and/or to cause one or more of
its subsidiaries to pay Executive, and Executive agrees to accept the following amounts and
benefits (all Dollar amounts referred to herein are in United States Dollars):

(a)   Base Salary:

     During the term hereof, Executive shall receive an annual base salary (“Base Salary”) of Six
Hundred Thousand Dollars ($600,000), as it may be increased from time to time at the discretion of
the Employer’s Board of Directors (the “Board of Directors”), upon advice and consent of the
Compensation Committee of the Board of Directors (the “Compensation Committee”), pro rated for any
calendar year within the Term for which employment does not extend for the entire calendar year.
The Base Salary shall be paid to Executive in equal bi-weekly installments.

(b)   Bonus Pool:

     Executive shall participate in the bonus pool (the “Bonus Pool”) created with respect to each
accident underwriting year, consisting of that portion of the underwriting profit for such year
designated by the Board of Directors, and the Board of Directors shall establish performance
criteria upon which Executive’s bonus shall be determined. During Executive’s employment under
this Agreement, Executive shall be eligible to receive a target bonus of 100% of Base Salary,
although it is agreed that actual bonus awards may exceed, match or be less than the target bonus,
as Executive’s performance or Employer’s performance warrant. The form of payment and other terms
and

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conditions of such bonus shall be determined by Employer, upon advice and consent of the
Compensation Committee. Notwithstanding the foregoing, to the extent Executive is a “covered
employee” within the meaning of Section 162(m) of the Internal Revenue Code of 1986, as amended
(the “Code”), the annual bonus may be implemented and administered in a manner intended to insure
the treatment of such bonus as “performance-based compensation” within the meaning of Section
162(m) of the Code (including, without limitation, by having the relevant performance goals
established by the Compensation Committee of the Board of Directors and having the Compensation
Committee certify the achievement of such goals before the annual bonus is paid).

     Bonuses will be paid on or about March 15 of the year following the related accident
underwriting year (and in no event later than April 15 of the year following the related accident
underwriting year).

(c)   Restricted Stock Grant:

     (i)   As consideration for entering into this Agreement, Executive shall receive an award of
that number of restricted shares (the “Restricted Shares”) of Employer, consisting of its Common
Stock, par value $.01 per share, which when multiplied by the simple average of the closing prices
of such common stock on the New York Stock Exchange on the twenty (20) business days next preceding
July 31, 2009, yields the aggregate sum of One Million Dollars ($1,000,000), and, subject to
subparagraphs (ii) and (iii) below, the foregoing grant shall be subject to the terms of Employer’s
Restricted Share Plan (the “Restricted Share Plan”). Executive shall become vested in the shares
granted pursuant to the foregoing sentence, and all restrictions shall lapse, on August 15, 2012.

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     (ii)   An award document evidencing the foregoing Restricted Share grant (the “Award
Document”) shall be provided to Executive by Employer within 30 days of the date of execution
hereof. The Award Document shall provide that (a) upon Executive’s Termination of Employment as a
result of death, disability, reaching retirement age, Change in Control (as defined in Article II,
Section 7 below), termination by Executive as a result of a Constructive Termination (as defined in
Article II, Section 4 below), or termination by Employer for reasons other than For Cause (as
defined in Article II, Section 3 below) the restricted period applicable to any Restricted Shares
granted to Executive thereunder (an “Award”) shall terminate and Executive shall become fully
vested in such Award; and (b) if the stock of Employer at any time during the restricted period
ceases to be publicly traded, then Executive shall have the option to receive a cash payment,
payable by Employer within ten (10) days following written notice from Executive no later than
thirty (30) days following the delisting of Employer stock from the exchange, equal to the number
of shares of Restricted Stock of Employer granted under the Award Document and held by Executive as
of the delisting of the stock times the greater of (i) the share price of Employer stock as of the
close of business forty-five (45) trading days prior to its delisting and (ii) the average share
price of Employer stock (based on end of business day values) over the forty-five (45) trading day
period prior to delisting. To the extent the cash payment exceeds the fair market value of the
stock at the time of payment and Executive is a “specified employee” as defined in Section 409A of
the Code, the excess amount shall be paid the earlier of (A) six (6) months following termination
of employment, or (B) death. The foregoing subparagraph (b) shall not apply if the stock of
Employer ceases to be publicly traded as a result of Employer having made

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a general assignment for the benefit of creditors, been adjudicated as bankrupt or insolvent, or
having filed a voluntary petition in bankruptcy, a petition or answer seeking an arrangement with
creditors or to take advantage of any insolvency law or having filed an answer admitting the
material allegations of a petition filed against Employer in bankruptcy.

     (iii)   Employer will take whatever action necessary, including, without limitation, amendment
of the Restricted Share Plan, to ensure that the issuance of Restricted Shares by Employer to
Executive pursuant to the Award Document does not exceed the maximum number of shares available for
such purpose.

(d)   Previously Awarded Restricted Stock:

     As consideration for entering Executive’s employment with Employer, effective as of August 15,
2006, Executive was granted 36,621 Restricted Shares (the “2006 Award”) of Employer’s common stock
pursuant to Employer’s Restricted Share Plan. Pursuant to the terms of the grant, the 2006 Award
was originally scheduled to vest with respect to twenty percent (20%) of the Restricted Shares on
August 15, 2007, and on each anniversary thereafter with respect to an additional twenty percent
(20%), such that on August 15, 2011, all restrictions would have lapsed on the 36,621 Restricted
Shares comprising the 2006 Award. Upon the execution of this Agreement, the remaining 21,972
outstanding and unvested Employer Restricted Shares granted to Executive under the 2006 Award shall
fully vest and all restrictions shall lapse.

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(e)   Living Allowance:

     (i)   During the term of this Agreement, for such time as Executive’s principal residence is in
the State of Texas, Executive shall be entitled to a bi-weekly living allowance (“Living
Allowance”) of $3,000. Each bi-weekly payment of the Living Allowance shall be “grossed up” such
that after all federal, state, local and other withholdings and similar taxes and payments required
by applicable law have been deducted, Executive will receive the amount stated in the previous
sentence. This Section 3(e)(i) shall no longer apply upon Executive’s relocation as described in
Section 3(e)(ii) below.

     (ii)   In the event that Executive relocates his principal residence to the New York
Metropolitan Area, Executive shall be eligible to participate in such benefits and perquisites as
are now generally available to executive officers of Employer that transfer from an affiliate
company, including, without limitation, the prompt payment, or reimbursement to Executive upon
presentation of appropriate substantiation, the following relocation expenses: (a) packing, moving,
storage and travel expenses reasonably incurred by Executive in connection with moving Executive,
Executive’s immediate family, and their possessions; (b) home sale and purchase closing costs,
including loan origination fees, brokers’ fees and commissions, home appraisal and inspection fees,
title costs, attorney and escrow office fees, recording fees, and state and local recording,
transfer and real property gains taxes, etc., reasonably incurred by Executive in connection with
Executive and Executive’s family moving from their residence; and (c) such other expenses
reasonably related to Executive’s move.

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(f)   Additional Benefits:

     During the term of this Agreement, Executive shall be entitled to the following fringe
benefits:

     (i)   Executive Benefits: Executive shall be eligible to participate in such benefits and
perquisites as are now generally available or later made generally available to executive officers
of Employer or its subsidiaries.

     (ii)   Vacation: Executive shall be entitled to vacation time consistent with his position as
Executive Vice President and Chief Financial Officer of Employer.

     (iii)   Life Insurance: Executive shall be eligible to participate in any life insurance program
available to executive officers of Employer or its subsidiaries on terms at least as favorable as
those generally made available to such executive officers.

     (iv)   Disability Insurance: Executive shall be eligible to participate in any disability
insurance program available to executive officers of Employer or its subsidiaries on terms at least
as favorable as those generally made available to such executive officers.

     (v)   Reimbursement for Expenses: Employer shall reimburse Executive for reasonable and properly
documented out-of-pocket business and/or entertainment expenses incurred by Executive in connection
with his duties under this Agreement, consistent with Employer’s Travel and Entertainment Policy.

     (vi)   Reimbursement of Attorney’s Fees: Employer shall pay all reasonable attorney’s fees and
disbursements incurred by Executive in drafting and negotiating this Agreement; payment shall be
made either to Executive upon submission of paid invoices for such legal work or directly to the
Attorney chosen by Executive.

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     (vii)   Retirement Plans and Related Arrangements: Executive shall continue to participate
in all retirement plans and arrangements made available to Employer’s executives, and for purposes
of all such plans and arrangements, Employer shall credit Executive’s vesting service with Employer
and any of its affiliates, including its majority stockholder, Fairfax Financial Holdings Limited
(“Fairfax”) and its subsidiaries, since April 15, 1999.

ARTICLE II

TERMINATION OF EMPLOYMENT

     Subject to Section 8 of this Article II, Employer shall provide Executive with the following
payments and benefits upon termination of employment:

Section 1:   Termination Due to Death.

     The employment of Executive under this Agreement shall terminate upon Executive’s death. In
the event of Executive’s death during Executive’s employment hereunder, the estate or other legal
representative of Executive shall be entitled to receive the following:

(a)   Base Salary:

     Employer shall pay to Executive’s estate or other legal representative of Executive,
Executive’s Base Salary and Living Allowance, if then applicable, for the period ending one year
following the month in which Executive dies. Such an amount and all other amounts payable under
this Section 1 of Article II shall be paid by Employer in a lump sum within thirty (30) days of the
date of death, provided, however, that the
amounts due with respect to the Bonus Pool shall be paid when such amounts would ordinarily be
paid.

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(b)   Payment from Bonus Pool:

     Employer shall pay to the estate or other legal representative of Executive, (i) all amounts
accrued in the Bonus Pool by Executive with respect to years preceding the year in which the death
of Executive occurs and (ii) the pro-rated bonus payable with respect to the year in which the
death of Executive occurs.

(c)   Restricted Stock:

     Upon the death of Executive, the restricted period with respect to all Restricted Stock
previously awarded to Executive including, without limitation, Restricted Stock of Employer
awarded pursuant to this Agreement, shall terminate and the Executive’s estate or other legal
representative shall become fully vested in all Restricted Stock previously awarded to Executive.
In addition, upon the death of Executive, all other equity awards, if any, shall vest (and, with
respect to stock options and stock appreciation rights, if any, shall become fully exercisable).

Section 2:   Termination by Reason of Disability.

     If, during the term of this Agreement, Executive, in the judgment of the Board of Directors,
has failed to perform his duties under this Agreement on account of illness or physical or mental
incapacity, and such illness or incapacity continues for a period of more than (i) six (6)
consecutive months or (ii) one hundred eighty three (183) days in any consecutive three hundred
sixty-five (365) day period, Employer shall have the right to commence process to terminate
Executive’s employment under this Agreement on

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account of disability. Employer shall send written notice to Executive of (x) its intention to
commence such process, (y) a medical doctor chosen by Employer to make the determination referred
to in the next sentence, and (z) Executive’s right within ten (10) days of receipt of the notice to
choose a second medical doctor to make such determination. Termination for disability shall be
based on a determination that Executive is either unable to engage in any substantial gainful
activity by reason of any medically determinable physical or mental impairment that can be expected
to result in death or last for a continuous period of not less than 12 months; or by
reason of any medically determinable physical or mental impairment that can be expected to result
in death or last for a continuous period of not less than 12 months, is receiving income
replacement benefits for a period of not less than three months under an accident and health plan
covering employees of the service provider’s employer. Executive shall fully cooperate in this
process, including by making himself available for and consenting to all examinations and tests
required by any doctor making the aforesaid determination. The aforesaid determination shall be
made by the medical doctor chosen by Executive, if Executive exercises his foregoing right to
choose a doctor, and the medical doctor chosen by Employer. If the determination is being made by
two medical doctors and they cannot agree within fifteen (15) days of their both being chosen, they
shall as soon as reasonably possible select a third medical doctor to make the determination, who
shall make the determination within fifteen (15) days of being chosen. The determination made by
the foregoing process shall be conclusive. In the event the Executive’s employment is terminated on
account of disability, Executive’s rights to compensation and benefits shall be as follows:

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(a)   Base Salary:

     Executive shall be paid his pro rated Base Salary, as determined in accordance with the terms
of Section 3(a) of Article I for a period of no less than one year, less any benefits paid to him
under disability insurance policies maintained by Employer, until his termination on account of
disability.

(b)   Payment from Bonus Pool:

     Employer shall pay to Executive, when the same would ordinarily be paid, (i) all amounts
accrued in the Bonus Pool by Executive with respect to years preceding the year in which
termination due to disability of Executive occurs and (ii) the pro-rated bonus payable with respect
to the year in which termination due to the disability of Executive occurs.

(c)   Restricted Stock:

     The restricted period with respect to all Restricted Stock previously awarded to Executive
shall terminate and Executive shall become fully vested in all Restricted Stock previously awarded
to Executive, including, without limitation, Restricted Stock awarded pursuant to this Agreement.
In addition, all other equity awards shall vest (and, with respect to stock options and stock
appreciation rights, if any, shall become fully exercisable).

(d)   Living Allowance:

     Executive shall be paid his pro rated Living Allowance, as determined in accordance with the
terms of Section 3(e) of Article I, until his termination on account of disability.

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Section 3:   Termination for Cause.

     “Termination for Cause” shall mean termination by Employer of Executive’s employment by
Employer by reason of:

     (i)   a willful failure by Executive in bad faith to substantially perform his duties with
Employer resulting in material harm to Employer; or

     (ii)   Executive’s conviction of a felony involving moral turpitude.

     Executive must be given written notice that Employer intends to terminate Executive’s
employment for Cause. Such written notice shall specify the particular act or failure to act
constituting the basis of the intention to so terminate employment. In the case of a Termination
for Cause under clause (i) above, Executive shall be given the opportunity, within twenty (20) days
of the receipt of such notice, to meet with the Board of Directors to refute or explain such act or
failure to act. If such act or failure to act is reasonably determined by the Board of Directors to
be in violation of Section 3, clause (i), Executive shall be given ten (10) days after such meeting
to correct such act or failure to act, and upon failure of Executive within such ten (10) day
period to correct such act or failure to act to the reasonable satisfaction of the Board of
Directors, Executive’s employment by Employer shall be terminated. In the case of Termination for
Cause under (ii) above, Executive’s employment shall be terminated as of the date such notice is
given.

     In the event the Board of Directors shall terminate Executive’s employment for Cause,
Executive shall be entitled to receive the following:

(a)   Base Salary and Living Allowance:

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     Within thirty (30) days of the date of Executive’s Termination for Cause, Executive shall be
paid his pro rated Base Salary, as determined in accordance with the terms of Section 3(a) of
Article I, and his Living Allowance, if applicable, as determined in accordance with the terms of
Article I, Section 3(e), through the date of termination of employment.

(b)   Payment from Bonus Pool:

     Executive shall forfeit all rights to payments from the Bonus Pool.

Section 4:   Termination without Cause; Constructive Termination.

     Notwithstanding anything in this Agreement to the contrary, Executive’s employment
hereunder may be terminated by Employer without Cause, and Executive may terminate his
employment hereunder in the case of a Constructive Termination as defined in this Section 4,
provided, however, that in the event that Executive’s employment is terminated
in accordance with the terms of this Section 4, Executive shall be entitled to receive the
following:

(a)   Base Salary and Living Allowance:

     Within thirty (30) days of his termination of employment, Employer shall pay to Executive a
lump sum payment equal to:

     (i)   his Base Salary, as determined in accordance with the terms of Section 3(a) of Article I,
for the month in which termination occurs, and for the period incepting the first day of the month
immediately following the month in which termination occurs to the end of the Term, or any
extension thereto, inclusive (but in no event for less than one (1) year); and

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     (ii)   his Living Allowance, if then applicable, as determined in accordance with the terms of
Section 3(e) of Article I, through the date of termination of employment (or, if longer, the end of
the lease term for his temporary living quarters in the New York Metropolitan area; provided,
however, that Executive shall use reasonable efforts to sublease the premises or assign the lease
agreement, and in such event the Living Allowance shall not be paid to the extent Executive’s
obligations under the lease are relieved).

(b)   Payment from Bonus Pool:

     Employer shall pay to Executive, within thirty (30) days following termination of employment,
(i) all amounts accrued in the Bonus Pool by Executive with respect to years preceding the year in
which termination of employment of Executive occurs and (ii) the pro-rated bonus determined under
the Bonus Pool with respect to the year in which termination of employment of Executive occurs.

(c)   Restricted Stock:

     (i)   The restricted period applicable to all Restricted Stock previously awarded to Executive
shall terminate and the Executive shall become fully vested in all Restricted Stock previously
awarded to Executive, including, without limitation, Restricted Stock awarded pursuant to this
Agreement. Executive shall, upon such termination, have the option to take cash in lieu of
Restricted Stock with respect to all, or any portion, of the shares of Restricted Stock that vest
as a result of this subparagraph, based on a share price for such Restricted Stock that is the
greater of (a) the share price of Employer stock as of the close of business on the business day
next preceding the date of termination of employment and (b) the share price of Employer stock ten
(10) business days prior to the

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date determined under paragraph (a) above (or the closing price of the next preceding business day,
if such date does not fall on a business day). To the extent the cash payment exceeds the fair
market value of the stock at the time of payment and Executive is a “specified employee” as defined
in Section 409A of the Code, the excess amount shall be paid the earlier of (A) six (6) months
following termination of employment or (B) death. In addition, all other equity awards shall vest
(and, with respect to stock options and stock appreciation rights, if any, shall become fully
exercisable).

     (ii)   Executive shall give Employer written notice within ten (10) business days following
termination of employment under this Section 4 specifying the number of shares of Restricted Stock
with respect to which Executive has elected to take cash in lieu of shares of Restricted Stock.
Employer shall within thirty (30) days of receipt of such notice deliver to Executive a check in
payment of the value of the shares of Restricted Stock as determined in the immediately preceding
sentence and share certificates evidencing the remaining shares of Restricted Stock that have
vested as a result of termination of employment under this Section 4 and with respect to which
Executive has not exercised his election to take cash in lieu of shares.

(d)   Health Coverage.

     Executive’s medical and dental coverage shall cease upon the termination of the Executive’s
employment. In the event of such termination in accordance with the terms of this Section 4,
Employer shall provide Executive with notice and enrollment materials confirming Executive’s right
to continue medical and dental insurance coverage to the extent permitted under COBRA;
provided, however, that Executive shall only be required

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to pay the premiums charged to similarly-situated active employees during the entire COBRA
continuation period, and Employer shall pay the remaining cost of coverage.

     For purposes of this Agreement, “Constructive Termination” shall mean the termination of
employment by Executive following written notice to Employer for any of the following reasons:

     (i)   without Executive’s express written consent, the loss of Executive’s position described in
Article I, Section 1 or a material alteration in Executive’s position or responsibility as so
described;

     (ii)   without Executive’s express written consent, a breach by Employer of any of its material
obligations set forth in this Agreement;

     (iii)   any failure by a successor to Employer to assume Employer’s obligations under this
Agreement, either expressly or by operation of law, or, if Employer sells all or substantially all
of its assets, or as a result of a sale by Employer’s majority stockholder, Fairfax of all of its
holdings of Employer or a controlling interest in Employer, and in either case, as a result
thereof, any failure by the purchaser to assume Employer’s obligations under this Agreement; or

     (iv)   without Executive’s express written consent, relocation of Executive’s work situs to a
location that is not in the New York Metropolitan area.

     Executive must give written notice to Employer within ninety (90) days following the initial
existence of one or more of the reasons listed above if Executive intends to terminate Executive’s
employment because of the occurrence of one of the circumstances constituting Constructive
Termination under this Section 4. Such written notice shall

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specify the particular act or failure to act constituting the basis of Executive’s claim that
Constructive Termination has occurred. Employer shall be given the opportunity, within thirty (30)
days of the receipt of such notice, to fully cure any such act or failure to act.

     Notwithstanding any provision of this Agreement to the contrary, if, at the time of
Executive’s termination of employment with the Employer, Executive is a “specified employee” as
defined in Section 409A of the Code, and one or more of the payments or benefits received or to be
received by Executive pursuant to this Agreement would constitute deferred compensation subject to
Section 409A, no such payment or benefit will be provided under this Agreement until the earliest
of (A) the date which is six (6) months after his “separation from service” for any reason, or (B)
death. If any payment is delayed pursuant to the above sentence, the first payment after such
delay expires shall include all amounts not previously paid as a result of such delay. The
determination of whether Section 409A of the Code requires any such delay shall be made by
Employer, after consultation with Executive’s tax counsel. The provisions of this paragraph shall
only apply to the extent required to avoid Executive’s incurrence of any penalty tax or interest
under Section 409A of the Code or any regulations or Treasury guidance promulgated thereunder. In
addition, if any provision of this Agreement would cause Executive to incur any penalty tax or
interest under Section 409A of the Code or any regulations or Treasury guidance promulgated
thereunder, Employer shall reform such provision to maintain to the maximum extent practicable the
original intent of the applicable provision without violating the provisions of Section 409A of
the Code.

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Section 5:   Non-Extension of Employment.

     Employer shall provide Executive written notice (“Notice”) of its intention not to extend
Executive’s employment under the terms of this Agreement (“Non-Extension of Employment”) at least
ninety (90) days prior to the end of the Term, and in such event, Executive’s employment with
Employer shall terminate upon the completion of the final day of the Term. In the event of
Non-Extension of Employment in accordance with the terms of this Section 5, Executive shall be
entitled to receive the following:(a) Base Salary; Health Coverage:

     Employer shall continue to pay Executive the Base Salary (at the rate in effect at the end of
the Term) for twelve (12) months following Executive’s termination of employment at such intervals
as the same would have been paid to Executive had Executive remained in the active service of
Employer. Executive’s medical and dental coverage shall cease upon the termination of Executive’s
employment. In the event of such termination in accordance with the terms of this Section 5,
Employer shall provide Executive with notice and enrollment materials confirming Executive’s right
to continue medical and dental insurance coverage to the extent permitted under COBRA;
provided, however, that Executive shall only be required to pay the premiums
charged to similarly-situated active employees during the entire COBRA continuation period, and
Employer shall pay the remainder of the cost of coverage.

(b)   Payment from Bonus Pool:

     Employer shall pay to Executive, thirty (30) days following the end of the Term, (i) all
amounts accrued in the Bonus Pool by Executive with respect to years preceding the year in
which Non-Extension of Employment occurs and (ii) the pro-
rated bonus payable with respect to the year in which Non-Extension of Employment occurs.

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(c)   Restricted Stock:

     (i)   The restricted period applicable to all Restricted Stock previously awarded to
Executive shall terminate and Executive shall become fully vested in all Restricted Stock
previously awarded to Executive, including, without limitation, Restricted Stock awarded
pursuant to this Agreement. Executive shall, upon such termination, have the option to take
cash in lieu of Restricted Stock with respect to all, or any portion, of the shares of
Restricted Stock that vest as a result of this subparagraph, based on a share price for such
stock which is the greater of (a) the share price of Employer as of the close of business on
the business day next preceding the date of termination of employment and (b) the share price
ten (10) business days prior to the date determined under paragraph (a) above (or the closing
price of the next preceding business day, if such date does not fall on a business day). To
the extent the cash payment exceeds the fair market value of the stock at the time of payment
and Executive is a “specified employee” as defined in Section 409A of the Code, the excess
amount shall be paid the earlier of (A) six (6) months following termination of employment, or
(B) death. In addition, all other equity awards, if any, shall vest (and, with respect to
stock options and stock appreciation rights, shall become fully exercisable).

     (ii)   Executive shall give Employer written notice within ten (10) business days following
termination of employment under this Section 5 specifying the number of shares of Restricted Stock
with respect to which Executive has elected to take cash in lieu

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of shares of Restricted Stock. Employer shall within thirty (30) days of receipt of such
notice deliver to Executive a check in payment of the value of the shares of Restricted Stock as
determined in the immediately preceding subsection and share certificates evidencing the remaining
shares of Restricted Stock that have vested as a result of termination of employment under this
Section 5 and with respect to which Executive has not exercised his election to take cash in lieu
of shares.

     Notwithstanding any provision of this Agreement to the contrary, if, at the time of
Executive’s termination of employment with Employer, Executive is a “specified employee” as defined
in Section 409A of the Code, and one or more of the payments or benefits received or to be received
by Executive pursuant to this Agreement would constitute deferred compensation subject to Section
409A, no such payment or benefit will be provided under this Agreement until the earliest of (A)
the date which is six (6) months after Employee’s “separation from service” for any reason or (B)
death. If any payment is delayed pursuant to the above sentence, the first payment after such
delay expires shall include all amounts not previously paid as a result of such delay. The
determination of whether Section 409A of the Code requires any such delay shall be made by
Employer, after consultation with Executive’s tax counsel. The provisions of this paragraph shall
only apply to the extent required to avoid Executive’s incurrence of any penalty tax or interest
under Section 409A of the Code or any regulations or Treasury guidance promulgated thereunder. In
addition, if any provision of this Agreement would cause Executive to incur any penalty tax or
interest under Section 409A of the Code or any regulations or Treasury guidance promulgated
thereunder, Employer shall reform
such provision to maintain to the maximum extent practicable the original intent of the
applicable provision without violating the provisions of Section 409A of the Code.

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     For the avoidance of doubt, this Section 5 shall not apply to the extent Section 4 above is
applicable.

Section 6:   Voluntary Termination.

     Executive may terminate his employment under this Agreement voluntarily by giving no less
than sixty (60) days written notice to Employer of his intention to voluntarily terminate his
employment with Employer. “Voluntary Termination” shall mean termination by Executive of
Executive’s employment by Employer other than (i) Constructive Termination as described in Section
4, (ii) “Termination Upon a Change in Control,” as described in Section 7, or (iii) termination by
reason of Executive’s death or disability as described in Sections 1 and 2.

     In the event that Executive’s employment is voluntarily terminated by Executive, Executive’s
rights to compensation and benefits shall be identical to those to which he would be entitled had
he been Terminated for Cause, except that Employer shall pay to Executive, when the same would
ordinarily be paid, (i) all amounts accrued in the Bonus Pool by Executive with respect to years
preceding the year in which the Voluntary Termination of Executive occurs and (ii) the prorated
bonus payable with respect to the year in which termination of Executive occurs.

Section 7:   Termination Upon a Change of Control.

     “Termination Upon a Change in Control” shall mean the termination of Executive’s employment
by Employer or the successor company (otherwise than for
Cause as provided in Section 3 of this Article II) or by Executive in a Constructive
Termination, in either case within one year following a Change in Control.

22

 

     In the event that Executive’s employment is Terminated Upon a Change in Control, Executive’s
rights to compensation, Restricted Stock and benefits shall be identical to those to which he
would be entitled had he been terminated by Employer other than for Cause pursuant to Section 4,
provided, however, that the minimum severance benefit described in Section
4(a)(i) (relating to Base Salary) shall be no less than two (2) years.

     “Change in Control” shall mean (i) the time that Employer or its ultimate parent, Fairfax,
first determines that any person and all other persons who constitute a group (within the meaning
of Section 13(d)(3) of the Securities Exchange Act of 1934 (“Exchange Act”)) have, at a time when
no other person or group directly or indirectly beneficially owns securities carrying more than
forty-five percent (45%) of the votes attached to all outstanding securities of Employer or
Fairfax, acquired direct or indirect beneficial ownership (within the meaning of Rule 13d-3 under
the Exchange Act) of outstanding securities of Employer or Fairfax carrying more than twenty
percent (20%) of the votes attached to all outstanding securities of Employer or Fairfax, unless
a majority of the “Continuing Directors” approves the acquisition not later than ten (10)
business days after Employer or Fairfax makes that determination, or (ii) the first day on which
a majority of the members of Employer’s or Fairfax’s Board of Directors are not “Continuing
Directors”, or (iii) the time that the Controlling Shareholder of either Employer or Fairfax no
longer is the controlling shareholder, or (iv) the arm’s length sale of a majority interest in
Employer by Fairfax, or (v) a sale of substantially all of the

23

 

assets of Employer or Fairfax. For purposes of (iii) in the preceding sentence, the
“Controlling Shareholder” of Fairfax is one or more of V. Prem Watsa, his family, corporations
controlled by, or trusts whose beneficiaries are, V. Prem Watsa or his family, the estate of V.
Prem Watsa (including the executors and administrators), and any persons to whom shares are
distributed or sold upon the death or by the estate of V. Preen Watsa or his family.

     “Continuing Directors” shall mean, as of any date of determination, any member of the Board of
Directors of Employer or Fairfax who (i) was a member of that Board of Directors on the date of
this Agreement, (ii) has been a member of that Board of Directors for the two years immediately
preceding such date of determination, or (iii) was nominated for election or elected to the Board
of Directors by the Controlling Shareholder or with the affirmative vote of all, or one less than
all, of the Continuing Directors who were members of the Board at the time of such nomination or
election.

Section 8:   Release.

     In consideration of the payments and benefits to be provided to the Executive under Sections
2, 4, 5, 6 and 7 of this Agreement, the Executive shall execute and deliver the Employer’s standard
waiver and release.

ARTICLE III

MISCELLANEOUS PROVISIONS

Section 1:   Payment Obligations.

24

 

     The obligation of Employer to pay Executive the compensation and to make the arrangements
provided herein shall be unconditional, and Executive shall have no obligation whatsoever to
mitigate damages hereunder. If litigation after a Change in Control (otherwise than in connection
with a Termination for Cause which is ultimately upheld in litigation) shall be brought to enforce
or interpret any provision contained herein, Employer, to the extent permitted by applicable law,
hereby indemnifies Executive for Executive’s reasonable attorney’s fees and disbursements incurred
in such litigation.

Section 2:   Confidentiality.

     Executive agrees that all confidential and proprietary information relating to the business of
Employer shall be kept and treated as confidential both during and after the term of this
Agreement, except as may be permitted in writing by the Board of Directors or as such information
is within the public domain or comes within the public domain without any breach of this Agreement.

Section 3:   Arbitration.

     Any dispute or controversy arising under or in connection with this Agreement that cannot be
mutually resolved by the parties hereto shall be settled exclusively by arbitration in New York,
New York under the employment arbitration rules of the American Arbitration Association before a
single arbitrator of exemplary qualifications and stature, who shall be selected jointly by
Employer and Executive, or, if Employer and Executive cannot agree on the selection of the
arbitrator, shall be selected by the American Arbitration Association. Judgment may be entered on
the arbitrator’s award in any court having jurisdiction. The parties hereby agree that the
arbitrator shall be

25

 

empowered to enter an equitable decree mandating specific enforcement of the terms of this
Agreement. The party that prevails in any arbitration hereunder shall be reimbursed by the other
party hereto for any reasonable legal fees and out of pocket expenses directly attributable to such
arbitration, and such other party shall bear all expenses of the arbitrator.

Section 4:   Withholdings.

     Unless otherwise provided herein, all compensation and benefits to Executive hereunder shall
be reduced by all federal, state, local and other withholdings and similar taxes and payments
required by applicable law.

Section 5:   Parachute Payments.

     Notwithstanding anything in this Agreement to the contrary, the amount of any payment or
benefit to be received by Executive pursuant to this Agreement or otherwise which would be subject
to the excise tax imposed by Section 4999 of the Code shall be reduced (but not below zero) by the
amount, if any, necessary to prevent any part of any such payment or benefit received or to be
received by Executive (such foregoing payments or benefits referred to collectively as the “Total
Payments”), from being subject to such excise tax, but only if and to the extent such reduction
will also result in, after taking into account all applicable state and Federal taxes (computed at
the highest applicable marginal rate), including any taxes payable pursuant to Section 4999 of the
Code, a greater after-tax benefit to Executive than the after-tax benefit to Executive of the Total
Payments computed without regard to any such reduction. For purposes of the foregoing, (a) no
portion of the Total Payments shall be taken into account which in the opinion of tax counsel
selected by Executive (“Tax Counsel”) does not constitute a

26

 

“parachute payment” within the meaning of Section 280G(b)(2) of the Code; (b) any reduction in
payments or benefits pursuant to this Agreement shall be computed by taking into account, in
accordance with Section 280G(b)(4) of the Code, that portion of the Total Payments which is
reasonable compensation, within the meaning of Section 280G(b)(4) of the Code, in the opinion of
Tax Counsel; (c) the value of any non-cash benefits or of any deferred or accelerated payments or
benefits included in the Total Payments shall be determined by a public accounting firm, selected
by Executive, in accordance with the principles of Section 280G(d)(3) and (4) of the Code and the
Treasury Regulations there; and (d) in the event of any uncertainty as to whether a reduction in
Total Payments to Executive is required pursuant hereto, the Employer shall initially make all
payments otherwise required to be paid to Executive hereunder, and any amounts so paid which are
ultimately determined not to have been payable hereunder (other than as a loan to Executive),
either (x) upon mutual agreement of Executive and Employer, or (y) upon Tax Counsel furnishing
Executive with its written opinion setting forth the amount of such payments not to have been so
payable (other than as a loan to Executive under this Section 5), or (z) in the event a portion of
the Total Payments shall be determined by a court or an Internal Revenue Service proceeding to have
otherwise been an “excess parachute payment,” to the extent permitted by law, the amount so
determined in (x), (y) or (z) shall constitute a loan by Employer to Executive under this Section
5, and Executive shall repay to Employer, within ten (10) business days after the time of such
mutual agreement, such opinion is so furnished to Executive, or of such determination, as
applicable, the amount of such loan plus interest thereon at the rate provided in Section
1274(b)(2)(B) of the Code for the period from the date of the initial
payments to Executive to the date of such repayment by Executive. All fees and expenses of any Tax
Counsel or accounting firm selected under this Section 5 shall be borne solely by Employer.

27

 

     All fees and expenses of any accounting firm selected under this Section 5 shall be borne
solely by Employer.

Section 6:   Indemnification.

     In addition to any rights to indemnification to which Executive is entitled under
Employer’s Articles of Incorporation and Bylaws, Employer shall indemnify Executive at all
times during and after the term of this Agreement to the maximum extent permitted under the
Delaware General Corporation Law and any successor provision thereof and any other applicable
corporate law, and shall pay Executive’s expenses in defending any civil or criminal action,
suit or proceeding in advance of the final disposition of such action, suit or proceeding and
any appeal thereof, to the maximum extent permitted under such applicable laws. Employer shall
use reasonable efforts to maintain at all times Directors and Officers Coverage comparable to
its existing Directors and Officers Coverage, if the same can be obtained at a reasonable cost
in comparison to the cost of the then existing coverage, to cover all or a portion of the
foregoing liability.

Section 7:   Notices.

     Any notices permitted or required under this Agreement shall be deemed given upon the date of
personal delivery, addressed to the Employer at:

     Odyssey Re Holdings Corp.

     300 First Stamford Place

     Stamford, Connecticut 06902

28

 

and addressed to Executive at the address on file with Employer or at any other address as either
party may, from time to time, designate by notice given in compliance with this Section.

Section 8:   Governing Law.

     This Agreement shall be governed by and construed in accordance with the substantive laws of
the State of New York.

Section 9:   Titles and Captions.

     All sections titles or captions contained in this Agreement are for convenience only and shall
not be deemed part of the context nor affect the interpretation of this Agreement.

Section 10:   Entire Agreement.

     This Agreement contains the entire understanding between the parties, and supersedes any prior
understandings and agreements between Executive and Employer and/or any affiliate of Employer
respecting the subject matter of this Agreement, including, without limitation, any representations
contained within public notices, press releases or regulatory filings previously issued or made by
Employer or Fairfax. No provision in this Agreement may be amended unless such amendment is set
forth in a writing that expressly refers to the provision of this Agreement that is being amended
and that is signed by Executive and by a representative of the Employer.

Section 11:   Agreement Binding.

     The Agreement shall be binding upon the heirs, executors, administrators, successors and
assigns of the parties hereto.

29

 

Section 12:   Computation of Time.

     In computing any period of time pursuant to this Agreement, the day of the act, event or
default from which the designated period of time begins to run shall be included, unless it is a
Saturday, Sunday or a legal holiday, in which event the period shall begin to run on the next day
which is not a Saturday, Sunday or legal holiday, and if the period ends on a Saturday, Sunday or
legal holiday, the period shall run until the end of the next day thereafter which is not a
Saturday, Sunday or legal holiday.

Section 13:   Pronouns and Plurals.

     All pronouns and any variations thereof shall be deemed to refer to the masculine, feminine,
neuter, singular or plural as the identity of the person or persons may require.

Section 14:   Presumption.

     This Agreement or any section thereof shall not be construed against any party due to the fact
that said Agreement or any section thereof was drafted by said party.

Section 15:   Further Action.

     The parties hereto shall execute and deliver all documents, provide all information and take
or forbear from all such action as may be necessary or appropriate to achieve the purposes of this
Agreement.

Section 16:   Parties in Interest.

     Nothing herein shall be construed to be to the benefit of any third party, nor is it intended
that any provision shall be for the benefit of any third party.

Section 17:   Savings Clause.

30

 

     If any provision of this Agreement, or the application of such provision to any person or
circumstance, shall be held invalid, the remainder of this Agreement, or the application of such
provisions to persons or circumstances other than those as to which it is held invalid, shall not
be affected thereby.

Section 18:   Failure to Enforce and Waiver.

     The failure to insist upon strict compliance with any of the terms, covenants or conditions of
this Agreement shall not be deemed a waiver of such terms, covenants or conditions, and the waiver
or relinquishment or any right or power under this Agreement at any one or more times shall not be
deemed a waiver or relinquishment of such right or power at any other time or times.

Section 19:   Counterparts; Facsimile Signatures.

     This Agreement may be executed in one or more counterparts, each of which will be deemed to be
an original copy of this Agreement and all of which, when taken together, will be deemed to
constitute one and the same agreement. This Agreement may be executed by facsimile signatures.

Section 20:   Headings.

     The headings of the Sections and sub-sections contained in this Agreement are for convenience
only and shall not be deemed to control or affect the meaning or construction of any provision of
this Agreement.

31

 

Section 21:   Section 409A Compliance.

     (i)   Anything in this Agreement to the contrary notwithstanding, any reimbursement payable to
Executive pursuant to any provisions of this Agreement, shall be paid no later than the last day of
the calendar year following the calendar year in which the related expense was incurred, except to
the extent that the right to reimbursement does not provide for a “deferral of compensation”
subject to Section 409A of the Code. No amount reimbursed during any calendar year shall affect
the amounts eligible for reimbursement in any other calendar year, and the right to reimbursement
or in-kind benefits shall not be subject to liquidation or exchange for another benefit.

     (ii)   Anything in this Agreement to the contrary notwithstanding, any payment that is delayed
as a result Executive being a “specified employee” as defined in Section 409A of the Code shall
commence earlier in the event of Executive’s death prior to the six-month anniversary of the date
of Executive’s termination of employment. Whenever a payment under this Agreement specifies a
payment period with reference to a number of days (e.g., “payment shall be made within
thirty (30) days following the date of

[Remainder of page intentionally left blank]

32

 

termination”), the actual date of payment within the specified period shall be within the sole
discretion of Employer.

Date:
August 3, 2009

ODYSSEY RE HOLDINGS CORP.

 

	 	 	 	 
	 	 	 
	By:  	/s/
Andrew A. Barnard	 
	 	ANDREW A. BARNARD, CHIEF EXECUTIVE OFFICER 	 
	 	 	 	 
	 
	 
	 
	 
	/s/
Richard Scott Donovan	 
	RICHARD SCOTT DONOVAN 	 
	 

33Exhibit 10.2 Amended and Restated Employment Agrmt

EXHIBIT 10.2

AMENDED AND RESTATED EMPLOYMENT AGREEMENT

This AMENDED AND RESTATED EMPLOYMENT AGREEMENT (this “Agreement”) is made and entered into as
of June 25, 2009 (the “Effective Date”) by and between Bridge Bancorp, Inc. (the “Company”), a New
York corporation, Bridgehampton National Bank (the “Bank”), a bank organized and existing under the
laws of the United States of America and a wholly owned subsidiary of the Company, and Howard H.
Nolan (the “Executive”).

WHEREAS, the Executive is currently employed as the Senior Executive Vice President and Chief
Administrative and Financial Officer of the Company and Bank pursuant to an employment agreement
between the Company, Bank and Executive originally entered into as of June 26, 2006, and
subsequently amended as of January 1, 2008 (the “Original Agreement”);

WHEREAS, the Company and Bank desire to amend and restate the Original Agreement in order to
make certain changes;

WHEREAS, the Company and Bank desire to ensure the continued availability of the Executive’s
services as provided in this Agreement;

WHEREAS, the Executive is willing to serve the Company and Bank on the terms and conditions
hereinafter set forth; and

NOW THEREFORE, in consideration of these premises, the mutual covenants contained herein, and
other good and valuable consideration the receipt and sufficiency of which are hereby acknowledged,
the parties hereto agree as follows:

1. Employment Period.

(a) Three Year Term. The Executive’s period of employment with the Bank and the
Company under the terms of this Agreement shall begin on the Effective Date and shall continue for
a period of thirty-six (36) months thereafter (the “Employment Period”).

(b) Annual Performance Evaluation. On a calendar year basis, the Bank and/or the
Company (acting through the full Board or a committee thereof) shall conduct an annual performance
evaluation of the Executive, the results of which shall be included in the minutes of the Board or
committee meeting and communicated to the Executive. The first such annual performance evaluation
shall occur in January 2010.

(c) Continued Employment Following Termination of Employment Period. Nothing in this
Agreement shall mandate or prohibit a continuation of the Executive’s employment following
the expiration of the Employment Period.

 

 

 

2. Duties.

(a) Title; Board Position, Responsibility. The Executive shall serve as the Senior
Executive Vice President and Chief Administrative and Financial Officer of the Bank and Company,
and shall perform such administrative and management services as customarily performed by person in
a similar executive capacity and as may be directed from time to time by the Chief Executive
Officer of the Company and Bank and/or the Board of Directors of the Company and/or Bank (the
“Board”). In his capacity as Senior Executive Vice President and Chief Administrative and
Financial Officer, the Executive shall report directly to the President and Chief Executive Officer
and to the Board. The Executive shall also continue to be a member of the Board. If Executive’s
employment with the Bank or the Company is terminated for any reason, his service on the Board
shall terminate, and this Agreement shall serve as Executive’s written resignation for that
purpose.

(b) Time Commitment. The Executive shall devote his full business time and attention
to the business and affairs of the Bank and the Company and shall use his best efforts to advance
the interests of the Bank and Company.

3. Annual Compensation.

(a) Annual Salary. In consideration for the services performed by the Executive under
this Agreement, the Bank shall pay to the Executive an annual salary (“Base Salary”) of not less
than $230,000. The Base Salary shall be paid in approximately equal installments in accordance
with the Bank’s customary payroll practices. The Bank shall review the Executive’s Base Salary at
least annually and such Base Salary may be increased, but may not be decreased without the
Executive’s consent (any increase in Base Salary shall become the new “Base Salary” for purposes of
this Agreement). The first such annual review of Executive’s performance and Base Salary shall
occur in January 2010.

(b) Board Meeting Fees. For his attendance at meetings of the Board of Directors of
the Bank and the Company (but not for committee meetings), the Executive shall receive such fees as
are paid to directors of the Bank and the Company for such attendance.

(c) Incentive Compensation. The Executive shall be eligible to participate in any
incentive compensation programs established by the Bank and/or the Company from time to time for
senior executive officers, in accordance with the terms of such plans as they may exist from time
to time.

(d) Equity Compensation. The Executive shall be eligible to participate in any equity
compensation programs established by the Bank and/or the Company from time to time for senior
executive officers, including, but not limited to, the 2006 Stock-Based Incentive Plan (the “2006
Plan”).

Nothing paid to Executive under any plan, program or arrangement referenced in (c) or (d)
above shall be deemed to be in lieu of other compensation to which Executive is entitled under this
Agreement.

 

2

 

4. Employee Benefit Plans; Paid Time Off

(a) Benefit Plans. During the Employment Period, the Executive shall be an employee
of the Bank and shall continue to participate in the Bank’s (i) tax-qualified retirement plans
(i.e., the defined benefit plan and 401(k) plan); (ii) the Bank’s Supplemental Executive Retirement
Plan; (iii) group life, health and disability insurance plans; and (iv) any other employee benefit
plans and programs in accordance with the Bank’s customary practices, provided he is a member of
the class of employees authorized to participate in such plans or programs.

(b) Paid Time Off. The Executive shall be entitled to paid vacation time each year
during the Employment Period, as well as sick leave, holidays and other paid absences, in
accordance with the Bank’s policies and procedures for executive employees.

5. Outside Activities and Board Memberships

During the term of this Agreement, the Executive shall not, directly or indirectly, provide
services on behalf of any financial institution, any insurance company or agency, any mortgage or
loan broker or any other entity or on behalf of any subsidiary or affiliate of any such entity
engaged in the financial services industry, as an employee, consultant, independent contractor,
agent, sole proprietor, partner, joint venturer, corporate officer or director; nor shall the
Executive acquire by reason of purchase during the term of this Agreement the ownership of more
than 5% of the outstanding equity interest in any such entity. Subject to the foregoing, and to
the Executive’s right to continue to serve as an officer and/or director or trustee of any business
organization as to which he was so serving on the Effective Date of this Agreement (as described in
an attachment to this Agreement or to the Original Agreement), the Executive may serve on boards of
directors of unaffiliated, for-profit business corporations, subject to Board approval, which shall
not be unreasonably withheld, and such services shall be presumed for these purposes to be for the
benefit of the Bank and the Company. Except as specifically set forth herein, the Executive may
engage in personal business and investment activities, including real estate investments and
personal investments in the stocks, securities and obligations of other financial institutions (or
their holding companies). Notwithstanding the foregoing, in no event shall the Executive’s outside
activities, services, personal business and investments materially interfere with the performance
of his duties under this Agreement.

6. Working Facilities and Expenses

(a) Working Facilities. The Executive’s principal place of employment shall be at the
Bank’s principal executive office or at such other location upon which the Bank and the Executive
may mutually agree.

 

3

 

(b) Expenses.

(i) Ordinary Expenses. The Bank shall reimburse the Executive for his ordinary and
necessary business expenses, incurred in connection with the performance of his duties under this
Agreement, upon presentation to the Bank of an itemized account of such expenses in such form as
the Bank may reasonably require. Any such expense shall be reimbursed no later than two and
one-half months following the end of the year in which the expense was incurred.

(ii) Automobile. The Bank shall provide the Executive with an automobile suitable to
the Executive’s position and such automobile may be used by the Executive in carrying out his
duties under this Agreement, including commuting between his residence and his principal place of
employment and other personal use. The Bank shall be responsible for the cost of maintenance and
servicing such automobile and for insurance, gasoline and oil for such automobile. The Executive
shall be responsible for the payment of any taxes on account of his personal use of such
automobile.

7. Termination of Employment with Bank Liability

(a) Reasons for Termination. In the event that the Executive’s employment with the
Bank and/or the Company shall terminate during the Employment Period on account of any of the
events set forth in Sections 7(a)(i) or 7(a)(ii) below (an “Event of Termination”), the Bank shall
provide the benefits and pay to the Executive the amounts provided for under Section 7(b) or
Section 7(c), as applicable:

	 	(i)	 	The Executive’s voluntary resignation from employment with the
Bank and the Company during the term of this Agreement within 30 days after the
occurrence of any of the following events without Executive’s consent, such
that the Executive’s resignation shall be treated as a resignation for “Good
Reason,” provided that for purposes of this Section 7(a)(i), the Executive must
provide not greater than ninety (90) days’ written notice to the Bank and the
Company of the initial existence of such condition and the Bank and the Company
shall have thirty (30) days to cure the condition giving rise to the Event of
Termination (but the Bank and the Company may elect to waive such thirty (30)
day period):

	 	(A)	 	the failure to re-appoint the Executive to the
officer position set forth under Section 2(a) and/or, the failure of
Executive to be appointed to
the Board of Directors of the Bank, and with respect to the
Executive’s service as a director of the Company, the failure to
re-nominate the Executive for election to the Board;

	 	(B)	 	a material change in Executive’s functions,
duties, or responsibilities, which change would cause Executive’s
position to become one of lesser responsibility, importance, or scope;

	 	(C)	 	a liquidation or dissolution of the Bank or the
Company other than a liquidation or dissolution that is caused by a
reorganization that does not affect the status of the Executive;

	 	(D)	 	a material breach of this Agreement by the Bank
and/or the Company; or

	 	(E)	 	the relocation of Executive’s principal place
of employment to an office other than one located in Southampton, East
Hampton, Shelter Island, Southold, Riverhead or Brookhaven, New York.

 

4

 

	 	(ii)	 	the involuntary termination of the Executive’s employment by
the Bank and/or the Company for any reason other than: for “Cause” as defined
in Section 8(a); for “Disability” as set forth in Section 7(d) below; in
connection with a Change in Control, as set forth in Section 7(c) below; or as
a result of the death of the Executive; provided that such involuntary
termination of employment constitutes a “Separation from Service” within the
meaning of Section 409A and the Treasury regulations thereunder.

(b) Severance Pay. Subject to the limitations set forth in Section 7(e) below, upon
an Event of Termination, the Bank shall pay to the Executive (or, in the event of the Executive’s
death after the event described in Section 7(a) has occurred, the Bank shall pay to the Executive’s
surviving spouse, beneficiary or estate) an amount equal to the following:

	 	(i)	 	his earned but unpaid Base Salary as of the date of his
termination of employment with the Bank;

	 	(ii)	 	the benefits to which he is entitled as a former employee under
the Bank’s employee benefit plans;

	 	(iii)	 	a lump sum cash payment, as liquidated damages, in an amount
equal to two (2) times the Executive’s Base Salary payable within ten (10)
business days following the Event of Termination; and

	 	(iv)	 	continued group health and medical insurance benefits (on the
same terms as such benefits are made available to other executive employees of
the Bank)
until the earlier to occur of (x) twenty-four (24) months following the
Event of Termination, or (y) Executive’s full time employment with another
employer.

(c) Change in Control. If within the period ending one year after a Change in Control
(as defined in Section 9 of this Agreement), (i) the Bank and/or the Company terminates the
Executive’s employment without Cause, or (ii) the Executive voluntarily terminates his employment
with Good Reason, the Bank will:

(i) pay a lump sum cash payment to Executive, as liquidated damages, within ten (10)
business days of the termination of the Executive’s employment, in an amount equal
to three (3) times the Executive’s annual compensation for the calendar year
immediately preceding the year in which the Change in Control occurs, and

(ii) provide continued group health and medical insurance benefits to Executive, (on
the same terms as such benefits are made available to other executive employees of
the Bank immediately prior to the Change in Control), until the earlier to occur of
(x) 36 months following Executive’s termination of employment, or (y) Executive’s
full time employment with another employer.

 

5

 

For purposes of Section 7(c)(i), annual compensation shall include all compensation reported
in the Executive’s annual (IRS) Form W-2 (Box 5) for the calendar year.

(d) Disability.

(i) In the event that during the term of this Agreement, Executive is unable to perform his
duties hereunder because he is disabled within the meaning of Code Section 409A and the Treasury
regulations thereunder (a “Disability”), the Executive shall be entitled to any and all benefits
under the Bank’s short-term and/or long-term disability insurance plan. During the first
twenty-four (24) months following termination of employment for Disability, the Bank and/or the
Company shall provide a supplemental monthly cash payment to Executive such that the payments
received by Executive on a monthly basis, from both disability insurance and this supplemental
payment shall equal the monthly rate of after-tax Base Salary being paid to Executive immediately
prior to such termination (the insurance payments may be taken into account on a tax-adjusted basis
if such payment are not subject to federal and/or state taxes).

(ii) Upon termination of Executive’s employment because of Disability, the Executive shall be
entitled to continued group health and medical insurance benefits for a period of twenty-four (24)
months following such termination, on the same terms as such benefits are made available to other
executive employees immediately prior to the Disability.

(e) Timing of Severance Pay. Any cash severance payments
shall be made in a lump sum within ten (10) business days of Executive’s termination of employment
subject to applicable withholding taxes. Such payments shall not be reduced in the event the
Executive obtains other employment following termination of employment with the Bank or following
the Change in Control. Notwithstanding anything herein to the contrary, if Executive is a
Specified Employee, as defined in Code Section 409A, and if any payment to be made under Section 7
shall be determined to be subject to Code Section 409A, then if required by Code Section 409A, such
payment or a portion of such payment (to the minimum extent possible) shall be delayed and shall be
paid on the first day of the seventh month following Executive’s Separation from Service pursuant
to Treasury regulation Section 1.409A-1(b)(9)(iii).

(f) Executive agrees that upon any termination of his employment, whether by Executive or by
the Bank or the Company, his service as a director of the Bank and the Company shall cease and he
shall be deemed to have resigned as a director effective upon such termination.

 

6

 

8. Termination without Additional Bank or Company Liability

(a) Termination for Cause.

(i) The Bank and/or the Company may terminate the Executive’s employment at any time, but any
termination other than termination for “Cause,” as defined herein, shall not prejudice the
Executive’s right to compensation or other benefits under the Agreement. The Executive shall have
no right to receive compensation or other benefits for any period after termination for “Cause.”
Termination for “Cause” shall mean termination because of: (i) the conviction of the Executive of a
felony or of any lesser criminal offense involving moral turpitude (other than for traffic
violations); (ii) the willful commission by the Executive of a criminal or other act that, in the
judgment of the Board or the President and Chief Executive Officer will likely cause substantial
economic damage to the Company, the Bank or any subsidiary or substantial injury to the business
reputation of the Company, the Bank or any subsidiary; (iii) the commission by the Executive of an
act of fraud in the performance of his duties on behalf of the Company, the Bank or any subsidiary;
(iv) the continuing willful failure of the Executive to perform his duties to the Company, the Bank
or any subsidiary (other than any such failure resulting from the Executive’s incapacity due to
physical or mental illness) after written notice thereof; (v) a material breach by the Executive of
the Bank’s Code of Ethics; or (vi) an order of a federal or state regulatory agency or a court of
competent jurisdiction requiring the termination of the Executive’s employment with the Bank or the
Company.

(ii) Executive shall not have the right to receive compensation or other benefits for any
period after the date of Termination for Cause. Notwithstanding the foregoing, Termination for
Cause shall not be deemed to exist unless there shall have been delivered to the Executive a copy
of a resolution duly adopted by the affirmative vote of not less than a majority of the entire
membership of the Board at a meeting of the Board called and held for the purpose (after reasonable
notice to the Executive and an opportunity for the Executive to be heard before the Board), finding
that in the good faith opinion of the Board the Executive was guilty of conduct described above and
specifying the particulars thereof. Prior to holding a meeting at which the Board is to make a
final determination whether Termination for Cause exists, if the Board determines in good faith at
a meeting of the Board, by not less than a majority of its entire membership, that there is
probable cause for it to find that the Executive was guilty of conduct constituting Termination for
Cause as described above, the Board may suspend the Executive from his/her duties hereunder for a
reasonable period of time not to exceed fourteen (14) days pending a further meeting at which the
Executive shall be given the opportunity to be heard before the Board. For purposes of this
subparagraph, no act or failure to act, on the Executive’s part shall be considered “willful”
unless done, or omitted to be done, by his/her not in good faith without reasonable believe that
his/her action or omission was in the best interest of the Company and the Bank.

 

7

 

(b) Death; Voluntary Resignation Without Good Reason. In the event that the
Executive’s employment with the Bank shall terminate during the Employment Period on account of the
reasons set forth in this Section 8(b), then the Bank shall have no further obligations under this
Agreement, other than the payment to the Executive of his earned but unpaid salary as of the date
of the termination of his employment, and the provision of such benefits, if any, to which he is
entitled as a former employee under the Bank’s employee benefit plans and programs and compensation
plans and programs, including without limitation, any incentive compensation plan. Termination of
employment under this Section 8(b) shall mean termination of employment due to the following
events:

	 	(i)	 	The Executive’s death; or

	 
	 	(ii)	 	The Executive’s voluntary resignation from employment with the
Bank for any reason other than the “Good Reason” as defined in Section 7(a)(i).

9. Change in Control

For purposes of this Agreement, the term “Change in Control” shall mean (i) a change in the
ownership of the Bank or the Company, (ii) a change in the effective control of the Bank or
Company, or (iii) a change in the ownership of a substantial portion of the assets of the Bank or
Company, as described below.

(A) A change in ownership occurs on the date that any one person, or more than one person
acting as a group (as defined in Treasury regulation section 1.409A-3(i)(5)(v)(B)), acquires
ownership of stock of the Bank or Company that, together with stock held by such person or group,
constitutes more than 50% of the total fair market value or total voting power of the stock of such
corporation.

(B) A change in the effective control of the Bank or Company occurs on the date that either
(i) any one person, or more than one person acting as a group (as defined in Treasury regulation
section 1.409A-3(i)(5)(v)(B)) acquires (or has acquired during the 12-month period ending on the
date of the most recent acquisition by such person or persons) ownership of stock of the Bank or
Company possessing 30% or more of the total voting power of the stock of the Bank or Company, or
(ii) a majority of the members of the Bank’s or Company’s board of directors is replaced during any
12-month period by directors whose appointment or election is not endorsed by a majority of the
members of the Bank’s or Company’s board of directors prior to the date of the appointment or
election, provided that this sub-section “(ii)” is inapplicable where a majority shareholder of the
Bank or Company is another corporation.

(C) A change in a substantial portion of the Bank’s or Company’s assets occurs on the date
that any one person or more than one person acting as a group (as defined in Treasury regulation
section 1.409A-3(i)(5)(vii)(C)) acquires (or has acquired during the 12-month period ending on the
date of the most recent acquisition by such person or persons) assets from the Bank or Company that
have a total gross fair market value equal to or more than 40% of the total gross fair market value
of (i) all of the assets of the Bank or Company, or (ii) the value of the assets being disposed of,
either of which is determined without regard to any liabilities associated with such assets. For
all purposes hereunder, the definition of Change in Control shall be construed to be consistent
with the requirements of Treasury regulation section 1.409A-3(g)(5).

 

8

 

10. Confidentiality. Unless the Executive obtains prior written consent from the Bank
or the Company, the Executive shall keep confidential and shall refrain from using for the benefit
of himself, or any person or entity other than the Bank, the Company or any entity which is a
subsidiary or affiliate of the Bank or the Company or of which the Bank or the Company is a
subsidiary or affiliate, any material document or information obtained from the Bank, the Company
or from any of their respective parents, subsidiaries or affiliates, in the course of his
employment with any of them
concerning their properties, operations or business (unless such document or information is readily
ascertainable from public or published information or trade sources or has otherwise been made
available to the public through no fault of his own) until the same ceases to be material (or
becomes so ascertainable or available); provided, however, that nothing in this Section 10 shall
prevent the Executive, with or without the Bank’s or the Company’s consent, from participating in
or disclosing documents or information in connection with any judicial or administrative
investigation, inquiry or proceeding to the extent that such participation or disclosure is
required under applicable law.

11. Non-Solicitation; Non-Competition; Post-Termination Cooperation.

(a) The Executive hereby covenants and agrees that, for a period of one year following his
termination of employment with the Bank, he shall not, without the written consent of the Bank,
either directly or indirectly:

(i) solicit, offer employment to, or take any other action intended (or that a reasonable
person acting in like circumstances would expect) to have the effect of causing any officer or
employee of the Bank, the Company or any of their respective subsidiaries or affiliates to
terminate his or her employment and accept employment or become affiliated with, or provide
services for compensation in any capacity whatsoever to, any business whatsoever that competes with
the business of the Bank or the Company or any of their direct or indirect subsidiaries or
affiliates or has headquarters or offices within the counties in which the Bank or the Company has
business operations or has filed an application for regulatory approval to establish an office; or

(ii) solicit, provide any information, advice or recommendation or take any other action
intended (or that a reasonable person acting in like circumstances would expect) to have the effect
of causing any customer of the Bank or the Company to terminate an existing business or commercial
relationship with the Bank or the Company.

(b) The Executive hereby covenants and agrees that following any termination of employment, he
shall not, without the written consent of the Bank, either directly or indirectly: become an
officer, employee, consultant, director, independent contractor, agent, sole proprietor, joint
venturer, greater than 5% equity-owner or stockholder, partner or trustee of any savings bank,
savings and loan association, savings and loan holding company, credit union, bank or bank holding
company, insurance company or agency, any mortgage or loan broker or any other entity that has its
main office, or a majority of its branch offices, east of the Shinnecock Canal. This restriction
shall apply for one year following termination. Notwithstanding the foregoing, the restriction
contained in this Section 11(b) shall not apply if the
Executive’s employment is terminated following a Change in Control.

 

9

 

(c) Executive shall, upon reasonable notice, furnish such information and assistance to the
Bank and/or the Company, as may reasonably be required by the Bank and/or the Company, in
connection with any litigation in which it or any of its subsidiaries or affiliates is, or may
become, a party; provided, however, that Executive shall not be required to provide information or
assistance with respect to any litigation between the Executive and the Bank, the Company or any of
its subsidiaries or affiliates.

(d) All payments and benefits to the Executive under this Agreement shall be subject to the
Executive’s compliance with this Section. The parties hereto, recognizing that irreparable injury
will result to the Bank, its business and property in the event of the Executive’s breach of this
Section 11, agree that, in the event of any such breach by the Executive, the Bank and/or the
Company will be entitled, in addition to any other remedies and damages available, to an injunction
to restrain the violation hereof by the Executive and all persons acting for or with the Executive.
The Executive represents and admits that the Executive’s experience and capabilities are such that
the Executive can obtain employment in a business engaged in other lines and/or of a different
nature than the Bank, and that the enforcement of a remedy by way of injunction will not prevent
the Executive from earning a livelihood. Nothing herein will be construed as prohibiting the Bank
and the Company from pursuing any other remedies available to them for such breach or threatened
breach, including the recovery of damages from the Executive.

12. Regulatory Requirements

(a) Notwithstanding anything herein contained to the contrary, any payments to Executive by
the Bank and/or the Company, whether pursuant to this Agreement or otherwise, are subject to and
conditioned upon their compliance with Section 18(k) of the Federal Deposit Insurance Act, 12
U.S.C. Section 1828(k), and the regulations promulgated thereunder in 12 C.F.R. Part 359.

(b) Notwithstanding any other provision in this Agreement, (i) the Bank or the Company may
terminate or suspend this Agreement and the employment of the Executive hereunder, as if such
termination were a Termination for Cause under Section 8(a) hereof, to the extent required by
federal or state laws or regulations related to banking, to deposit insurance or bank holding
companies or by regulations or orders issued by the Comptroller of the Currency, the Federal
Deposit Insurance Corporation or the Board of Governors of the Federal Reserve System and (ii) no
payment shall be required to be made to Executive under this Agreement to the extent such payment
is prohibited by applicable law regulation or order issued by a banking agency or a court of
competent jurisdiction; provided, that it shall be the Bank’s or the Company’s burden to prove that
any such action was so required.

 

10

 

13. Arbitration; Legal Fees.

(a) Arbitration. In the event that any dispute should arise between the parties as to
the meaning, effect, performance, enforcement, or other issue in connection with this Agreement,
which dispute cannot be resolved by the parties, the dispute shall be decided by final and binding
arbitration of a panel of three arbitrators. Proceedings in arbitration and its conduct shall be
governed by the rules of the American Arbitration Association (“AAA”) applicable to commercial
arbitrations (the “Rules”) except as modified by this Section. The Executive shall appoint one
arbitrator, the Bank shall appoint one arbitrator, and the third shall be appointed by the two
arbitrators appointed by the parties. The third arbitrator shall be impartial and shall serve as
chairman of the panel. The parties shall appoint their arbitrators within thirty (30) days after
the demand for arbitration is served, failing which the AAA promptly shall appoint a defaulting
party’s arbitrator, and the two arbitrators shall select the third arbitrator within fifteen (15)
days after their appointment, or if they cannot agree or fail to so appoint, then the AAA promptly
shall appoint the third arbitrator. The arbitrators shall render their decision in writing within
thirty (30) days after the close of evidence or other termination of the proceedings by the panel,
and the decision of a majority of the arbitrators shall be final and binding upon the parties,
nonappealable, except in accordance with the Rules and enforceable in accordance with the
applicable state law. Any hearings in the arbitration shall be held in Suffolk County, New York
unless the parties shall agree upon a different venue, and shall be private and not open to the
public. Each party shall bear the fees and expenses of its arbitrator, counsel, and witnesses, and
the fees and expenses of the third arbitrator shall be shared equally by the parties. The other
costs of the arbitration, including the fees of AAA, shall be borne as directed in the decision of
the panel.

(b) Legal Fees and Other Expenses. If the Executive is successful on the merits of
the dispute, as determined in the arbitration, all legal fees and such other expenses as reasonably
incurred by the Executive as a result of or in connection with or arising out of the dispute, shall
be paid by the Bank and/or the Company, provided that such payment or reimbursement is made by the
Bank not later than two and one-half months after the end of the year in which such dispute is
resolved in Executive’s favor.

14. Indemnification and Insurance. The Bank and/or the Company shall provide the
Executive (including his heirs, executors and administrators) with coverage under a standard
directors’ and officers’ liability insurance policy at its expense, and shall indemnify Executive
(and his heirs, executors and administrators) to the fullest extent permitted under applicable law
against all expenses and liabilities reasonably incurred by him in connection with or arising out
of any action, suit or proceeding in which he may be involved by reason of his having been an
officer of the Bank and/or the Company (whether or not he continues to be an officer at the time of
incurring such expenses or liabilities), such expenses and liabilities to include, but not be
limited to, judgments, court costs and attorneys’ fees and the cost of reasonable settlements (such
settlements must be approved by the Board); provided, however, that neither the Bank nor the
Company shall be required to indemnify or reimburse Executive for legal expenses or liabilities
incurred in connection with an action, suit or proceeding arising from any illegal or fraudulent
act committed by Executive. Any
such indemnification shall be made consistent with Section 18(k) of the Federal Deposit Insurance
Act, 12 U.S.C. §1828(k), and the regulations issued thereunder in 12 C.F.R. Part 359.

 

11

 

15. Notices. The persons or addresses to which mailings or deliveries shall be made
may change from time to time by notice given pursuant to the provisions of this Section. Any
notice or other communication given pursuant to the provisions of this Section shall be deemed to
have been given (i) if sent by messenger, upon personal delivery to the party to whom the notice is
directed; (ii) if sent by reputable overnight courier, one business day after delivery to such
courier; (iii) if sent by facsimile, upon electronic or telephonic confirmation of receipt from the
receiving facsimile machine and (iv) if sent by mail, three business days following deposit in the
United States mail, properly addressed, postage prepaid, certified or registered mail with return
receipt requested. All notices required or permitted to be given hereunder shall be addressed as
follows:

	 	 	 	 	 
	 

	 	If to the Executive:
	 	Howard H. Nolan
	 

	 	 	 	At the last address

On file
	 
	 	 	 	 
	 

	 	If to the Company	 	 
	 

	 	and the Bank:
	 	Bridgehampton National Bank
	 

	 	 	 	2200 Montauk Highway
	 

	 	 	 	Bridgehampton, New York 11932
	 

	 	 	 	Attention: President and Chief Executive Officer

With a copy to:

Luse Gorman Pomerenk & Schick, PC

5335 Wisconsin Avenue, NW, Suite 400

Washington, DC 20015

Attention: John J. Gorman, Esq.

16. Amendment. No modifications of this Agreement shall be valid unless made in
writing and signed by the parties hereto.

17. Miscellaneous.

(a) Notice of Termination. Any termination of Executive’s employment by the Bank
and/or the Company shall be communicated in writing to the Executive, and any voluntary termination
of employment by the Executive shall be communicated in writing to the Bank and/or the Company.

(b) Successors and Assigns. This Agreement will inure to the benefit of and be
binding
upon the Executive, his legal representatives and estate and intestate distributees, and the
Company and the Bank, their successors and assigns, including any successor by merger or
consolidation or a statutory receiver or any other person or firm or corporation to which all or
substantially all of the assets and business of the Bank or the Company may be sold or otherwise
transferred. Any such successor of the Bank or the Company shall be deemed to have assumed this
Agreement and to have become obligated hereunder to the same extent as the Company and Bank, and
the Executive’s obligations hereunder shall continue in favor of such successor.

(c) Severability. A determination that any provision of this Agreement is invalid or
unenforceable shall not affect the validity or enforceability of any other provision hereof.

 

12

 

(d) Waiver. Failure to insist upon strict compliance with any terms, covenants or
conditions hereof shall not be deemed a waiver of such term, covenant or condition. A waiver of
any provision of this Agreement must be made in writing, designated as a waiver, and signed by the
party against whom its enforcement is sought. Any waiver or relinquishment or any right or power
hereunder at any one or more times shall not be deemed a waiver or relinquishment of such right or
power at any other time or times.

(e) Counterparts. This Agreement may be executed in two or more counterparts, each of
which shall be deemed an original, and all of which shall constitute one and the same Agreement.

(f) Governing Law. This Agreement shall be governed by and construed and enforced in
accordance with the laws of the State of New York, without reference to conflicts of law
principles, except to the extent governed by federal law in which case federal law shall govern.

(g) Headings and Construction. The headings of sections in this Agreement are for
convenience of reference only and are not intended to qualify the meaning of any Section. Any
reference to a Section number shall refer to a Section of this Agreement, unless otherwise
specified.

(h) Entire Agreement. This instrument contains the entire agreement of the parties
relating to the subject matter hereof, and supersedes in its entirety any and all prior agreements,
understandings or representations relating to the subject matter hereof.

(i) Source of Payments. All payments provided in this Agreement shall be timely paid
in cash or check from the general funds of the Bank. The Company, however, unconditionally
guarantees payment and provision of all amounts and benefits due hereunder to Executive and, if
such amounts and benefits are not timely paid or provided by the Bank, such amounts and benefits
shall be paid or provided by the Company.

 

13

 

IN WITNESS WHEREOF, the Bank and the Company have caused this Agreement to be executed and the
Executive has hereunto set his hand, all as of the Effective Date specified above.

	 	 	 	 	 
	 	 	EXECUTIVE
	 
	 	 	 	 
	June 25, 2009	 	/s/ Howard H. Nolan
	 	 	 
	Date	 	Howard H. Nolan
	 
	 	 	 	 
	 	 	BRIDGE BANCORP, INC.
	 
	 	 	 	 
	June 25, 2009

	 	By:
	 	/s/ Marcia Z. Hefter
	 

	 	 	 	 
	Date

	 	 	 	Marcia Z. Hefter
	 

	 	 	 	Chairperson of the Board
	 
	 	 	 	 
	 	 	BRIDGEHAMPTON NATIONAL BANK
	 
	 	 	 	 
	June 25, 2009

	 	By:
	 	/s/ Marcia Z. Hefter
	 

	 	 	 	 
	Date

	 	 	 	Marcia Z. Hefter
	 

	 	 	 	Chairperson of the Board

 

14

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