Document:

Subscription Agreement

 EXHIBIT 10.1 
 JACKSONVILLE BANCORP, INC. 
 SUBSCRIPTION AGREEMENT 

Jacksonville Bancorp, Inc. 
 100 North Laura Street, Suite 1000 
 Jacksonville, Florida 32202 

Attn: Stephen C. Green 
 Ladies and Gentlemen: 

1.        Subscription. 

(a)        Subject to the terms and conditions of this Agreement, the undersigned
(the “Subscriber”), acting individually and not in concert with any other person, irrevocably subscribes (this “Subscription”) to purchase the number of shares set forth on the signature page hereto (the
“Shares”) of Noncumulative, Nonvoting, Perpetual Preferred Stock, Series B, $0.01 par value per share (the “Series B Preferred Stock”) of Jacksonville Bancorp, Inc. (the “Company”), at a purchase
price of $1,000.00 per Share. The Shares are being offered to the same accredited investors to whom shares of the Company’s Mandatorily Convertible, Noncumulative, Nonvoting, Perpetual Preferred Stock, Series A, $0.01 par value per share (the
“Series A Preferred Stock”) are being offered, in a private offering solely to accredited investors in a transaction exempt from registration under Section 4(a)(2) of the Securities Act of 1933, as amended (the
“Securities Act”) and Securities and Exchange Commission (“SEC”) Rule 506 thereunder (the “Private Placement”). 

(b)        The sale of the Shares to the Subscriber will occur at a date and time
mutually agreeable to the parties, but in any event within two days of acceptance of this Subscription by the Company. In consideration for the Shares, at the closing of such sale, the Subscriber shall pay to the Company, by check or wire transfer,
an amount equal to $1,000.00 multiplied by the number of Shares subscribed. 

(c)        The Subscriber has delivered or will deliver a completed and executed
copy of Internal Revenue Service Form W-9. 

2.        Representations, Warranties and Covenants of the Subscriber. The
Subscriber represents and warrants to, and agrees with, the Company as follows: 

(a)        No Public Solicitation. The Subscriber did not learn of the
Private Placement as a result of or subsequent to any general solicitation, advertisement, article, notice or other communication published in any newspaper, magazine or similar media or broadcast over the air or radio, or presented at any seminar
or meeting. 

 (b)        Investment has
Risks. The Subscriber understands that an investment in the Company is speculative and has a high degree of risk. The Subscriber has carefully considered such risks, and further understands that (i) no federal or state agency has
passed upon the merits of the offer or sale of Series B Preferred Stock in the Private Placement, (ii) no public or other market exists or is expected to exist for the Series B Preferred Stock and it may not be possible for the Subscriber to
liquidate the Shares, and (iii) there is no guarantee that the Subscriber will recover the initial investment in the Company contemplated by this Subscription or realize any gain from any such investment. 

(c)        Economic Risk of Loss and Sophistication. The Subscriber is
able to bear the economic risk of maintaining an illiquid investment for which there is no market and/or losing the entire investment in the Company contemplated by this Subscription. The Subscriber’s overall commitment to investments that are
not readily marketable is not disproportionate to the Subscriber’s net worth. The Subscription will not cause such overall commitment to become excessive. The Subscriber has such knowledge and experience in financial and business matters that
it is capable of evaluating the risks and merits of an investment in the Company. 

(d)        Status of Investor; Exempt Transaction. The Subscriber is an
“accredited investor” as defined in SEC Rule 501(a) of Regulation D under the Securities Act. The Subscriber understands that the shares of Series B Preferred Stock, including the Shares, the shares of the Series A Preferred Stock that the
Company may issue in exchange for the Shares pursuant to an Exchange Agreement between the Company and the Subscriber (the “Exchange Agreement”), and the shares of the Company’s common stock, $0.01 par value (the
“Common Stock”) into which such shares of Series A Preferred Stock are mandatorily convertible (collectively, the “Securities”), are being offered in reliance upon the exemption from federal securities registration
requirements set forth in section 4(a)(2) of the Securities Act and Rule 506 of Regulation D under the Securities Act. 
 (e)        No Registration. The Subscriber acknowledges and agrees that the Securities have not been registered under the Securities Act or the securities
laws of any other domestic or foreign jurisdiction. The Securities, therefore, cannot be resold by the Subscriber unless they are registered under the Securities Act and any necessary other domestic or foreign jurisdictions, or unless exemptions
from such necessary registrations are available. In that regard, and without limiting the generality of the foregoing, the Subscriber agrees not to offer, sell, pledge or otherwise dispose of all or any portion of the Securities or any interest
therein, except pursuant to an offering duly registered or qualified under the Securities Act and any applicable state securities laws, unless (i) in the opinion of counsel satisfactory to the Company, registration or qualification under the
Securities Act and any applicable state or foreign securities laws is not required, and (ii) the Subscriber has received all necessary regulatory approvals, if any. The Subscriber understands that a legend to the effect that the Securities have
not been so registered, and indicating the other restrictions on transferability identified in this Agreement, will be placed on any certificate representing the Securities and that stop transfer instructions to such effect may be issued by the
Company to its transfer agent. 
 (f)        Investment Intent.
The Subscriber is acquiring the Securities for its own account, and not with a view to any distribution thereof in violation of the Securities Act or any other applicable domestic or foreign securities law, and the Subscriber has no present plans to
enter into any contract, undertaking, agreement or arrangement for any such distribution. 

 3.    Covenants of the Company. The Company
acknowledges and agrees that the Subscriber has and is relying upon the Company’s representations and warranties, and the Company’s covenants and agreements, set forth in the Stock Purchase Agreement, dated August 22, 2012, between
the Company, the Subscriber, and the other investors parties thereto (as may be amended from time to time, the “Stock Purchase Agreement”). The Shares are not convertible into any other securities. The Subscriber, as a holder of the
Shares, shall be entitled to all of the rights of an Investor (as defined in the Stock Purchase Agreement) provided by the Stock Purchase Agreement with respect to any shares of Series A Preferred Stock held by the Investor as a result of any
exchange of shares of Series B Preferred Stock, for shares of Series A Preferred Stock, and any shares of Common Stock held as a result of a conversion of Series A Preferred Stock. 

4.    Miscellaneous. 

(a)        This Agreement may be executed in any number of counterparts, each of
which shall be deemed an original, but all of which together shall constitute one and the same instrument. Electronic or facsimile signatures will have the same effect as manually executed signatures. 

(b)        This Agreement shall be governed by and construed in all respects in
accordance with the laws of the State of Florida, without giving effect to principles governing conflicts of law. 
 (c)        The Company shall pay, upon invoice, all the expenses, including all legal fees and charges, including, without limitation, those fees and charges of
McGuireWoods LLP, Jones Day, and Sullivan & Cromwell, incurred by the Company and CapGen in connection with the offering, regulatory discussions and actions, and the purchase and exchange of Series B Preferred Stock. 

 
 [signature page follows] 

  
 -3-

 IN WITNESS WHEREOF, the undersigned Subscriber has executed this Agreement
as of September 27, 2012. 
 Number of Shares subscribed for: 5,000 

 

			
	SUBSCRIBER:
	
	CAPGEN CAPITAL GROUP IV LP
	BY:	 	 CAPGEN CAPITAL GROUP IV LLC,

AS GENERAL PARTNER OF CAPGEN

CAPITAL GROUP IV LP

  

			
	 By:
	 	 /s/ John R. Caughey

	 Name: John R. Caughey

	 Title: Vice President and Chief Financial Officer

 The Company hereby accepts the foregoing Subscription as to the number of Shares
set forth above, effective as of September 27, 2012. 
  

			
	JACKSONVILLE BANCORP, INC.
		
	By:	 	 /s/ Stephen C. Green

	Name: Stephen C. Green
	Title:   President and Chief Executive Officer

 [Signature Page to Subscription Agreement]Exchange Agreement

 EXHIBIT 10.2 
 JACKSONVILLE BANCORP, INC. 
 EXCHANGE AGREEMENT 

THIS EXCHANGE AGREEMENT, dated as of September 27, 2012 (this “Agreement”), is by and among
JACKSONVILLE BANCORP, INC., a Florida corporation (the “Company”), and CAPGEN CAPITAL GROUP IV LP, a Delaware limited partnership (“CapGen”), and each of the respective other investors, if any, set forth on the
signature pages to this Agreement (collectively, with CapGen, the “Investors”). 
 The Company
and the Investors are parties to a Stock Purchase Agreement dated as of August 22, 2012, which provides for the purchase of an aggregate of 50,000 shares of the Company’s Mandatorily Convertible, Noncumulative, Nonvoting Perpetual
Preferred Stock, Series A, liquidation preference $1,000.00 per share (the “Series A Preferred Stock”), at a purchase price of $1,000.00 per share (the “Share Price”) on the terms and subject to the conditions set
forth therein (the “Stock Purchase Agreement”). Capitalized terms used but not defined herein shall have the meanings set forth in the Stock Purchase Agreement. 

The Company has requested CapGen, and other Investors, to purchase Company nonvoting preferred stock prior to the receipt
by CapGen of the approvals from the Federal Reserve necessary for CapGen to purchase up to $25 million of Series A Preferred Stock pursuant to the Stock Purchase Agreement, so that the Company may provide additional capital to its subsidiary bank,
The Jacksonville Bank (the “Bank”). 
 The Company and the Investors have agreed that CapGen
and the other Investors, if any, shall purchase an aggregate of 5,000 shares of the Company’s 10% Noncumulative, Nonvoting Perpetual Preferred Stock, Series B (the “Series B Preferred Stock”) at $1,000.00 per share on or prior
to September 30, 2012, following the filing of Articles of Amendment to the Amended and Restated Articles of Incorporation of the Company with the Florida Secretary of State establishing the Series B Preferred Stock. The shares of Series B
Preferred Stock will be purchased pursuant to a Subscription Agreement between the Company and CapGen dated as of September 27, 2012. 
 The Company does not believe it is in its best interests to keep the Series B Preferred Stock outstanding upon and following the closing of the sale of Series A Preferred Stock contemplated by the Stock
Purchase Agreement and the issuance of the Series A Preferred Stock. 

 In consideration of the premises, and other good and valuable consideration,
the receipt of which is acknowledged, the parties, intending to be legally bound, agree as follows: 

1.        The Company agrees to exchange (the “Exchange”) all
issued and outstanding shares of Series B Preferred Stock at their aggregate Liquidation Preference (as defined in the Articles of Amendment designating the terms of the Series B Preferred Stock) for the number of shares of Series A Preferred Stock
having an aggregate liquidation preference as of the issuance of the Series A Preferred Stock equal to the aggregate Series B Preferred Stock Liquidation Preference. Such Exchange will be made simultaneously with the issuance of shares of Series A
Preferred Stock under the Stock Purchase Agreement to CapGen, and other Investors, if any, following CapGen’s receipt of Federal Reserve approval of CapGen’s purchase of Series A Preferred Stock for cash and in the Exchange. Any shares of
Series A Preferred Stock acquired in the Exchange will reduce CapGen’s and the other Investor’s respective obligations under the Stock Purchase Agreement (and the closing condition therein that Investors purchase an aggregate of $50
million in shares of Series A Preferred Stock) on a share-for-share basis. In no event will CapGen have any obligation to acquire or hold, collectively with CapGen’s affiliates, more than 49.9% of the Company’s outstanding common stock and
other “voting securities” (as defined in Federal Reserve, Regulation Y, § 225.2(q)(1)). 

2.        Alternatively, instead of the Exchange, the Company, at any time, in
its discretion, subject to receipt of any required regulatory approval, may redeem all outstanding shares of Series B Preferred Stock upon payment of the Liquidation Preference as of the redemption date. 

 
 [Signature Page Follows] 

 The parties have caused this Agreement to be executed as of the date first
above written by their respective duly authorized officials. 
  

			
	JACKSONVILLE BANCORP, INC.
		
	By:	 	   /s/ Stephen C. Green

		 	Name: Stephen C. Green
		 	Title: Chief Executive Officer

  

			
	CAPGEN CAPITAL GROUP IV LP
		
	BY:	 	CAPGEN CAPITAL GROUP IV LLC,
		 	AS GENERAL PARTNER OF CAPGEN
		 	CAPITAL GROUP IV LP

  

			
	By:	 	     /s/ John R.
Caughey            

		 	Name: John R. Caughey
		 	Title: Vice President and Chief Financial Officer

 [Signature Page to Exchange Agreement]

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