Company: OSBC
Filing Date: 2025-05-06
Form Type: S-4/A
Source: 0001104659-25-045103
Chunk: 118

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-06
Form: S-4/A
Chunk 118
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 this proxy statement/prospectus and is incorporated by reference into this proxy statement/prospectus. We urge you to read the voting agreement carefully and in its entirety.

Concurrently with the execution of the merger agreement Old Second and Bancorp Financial entered into a voting agreement with the directors of Bancorp Financial who are also Bancorp Financial stockholders, in their respective capacities as Bancorp Financial stockholders and not in their capacities as directors of Bancorp Financial, and certain other officers and stockholders of Bancorp Financial. As of the record date for the Bancorp Financial special meeting, 36.9% of the issued and outstanding shares of Bancorp Financial common stock were subject to Voting Agreements.

Pursuant to the voting agreement, each such director and stockholder agrees, among other things, to vote his or her shares of Bancorp Financial common stock in favor of the approval and adoption of the merger agreement at any meeting of stockholders of Bancorp Financial called to vote upon the merger and any other matter that is reasonably necessary to be approved by the stockholders of Bancorp Financial to facilitate the consummation of the merger, and against any proposal, transaction, agreement that is intended to or could reasonably be expected to prevent, impede, interfere with, materially delay, postpone, adversely affect or discourage the consummation of the transactions contemplated by the merger agreement and against any alternative acquisition proposal. Each such director and stockholder also agrees not to transfer his or her shares prior to the effective time of the merger or the termination of the merger agreement, subject to customary exceptions including charitable donations.

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TABLE OF CONTENTS

<div align='center'>**MATERIAL U.S. FEDERAL INCOME TAX CONSEQUENCES OF THE MERGER**</div>

The following discussion summarizes the anticipated material U.S. federal income tax consequences of the merger generally applicable to U.S. holders (as defined below) of Bancorp Financial common stock who exchange their shares of Bancorp Financial common stock for the merger consideration. This summary is based upon the Internal Revenue Code of 1986, as amended, which we refer to as the “Code,” Treasury regulations promulgated thereunder, judicial authorities, published positions of the Internal Revenue Service, which we refer to as the “IRS,” and other applicable authorities, all as in effect on the date of this discussion and all of which are subject to change (possibly with retroactive effect) and differing interpretations.

This summary is limited to U.S. holders (as