Company: OSBC
Filing Date: 2025-05-08
Form Type: 424B3
Source: 0001104659-25-046065
Chunk: 113

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-08
Form: 424B3
Chunk 113
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, or other legal restraint or prohibition enacted, issued, or enforced by any governmental authority that prohibits, makes illegal, or otherwise prevents the consummation of the merger, the bank merger, or any of the other transactions contemplated by the merger agreement;

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the authorization for listing on NASDAQ of the shares of Old Second common stock to be issued in the merger;

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receipt by each party of an opinion from its tax advisor or legal counsel as to certain tax matters;

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subject to materiality standards in the merger agreement, the accuracy of the representations and warranties of the other party;

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the prior performance in all material respects by the other party of the obligations, covenants, and agreements required to be performed by it at or before the closing date of the merger; and

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the absence of any change, state of facts, event, development, or effect, which, individually or in the aggregate has had or is reasonably expected to have a material adverse effect on the other party since February 24, 2025.

Old Second’s obligation to complete the merger is further subject to:

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the receipt by Bancorp Financial of all consents requested by Old Second that are necessary to renew or prevent a default or termination under certain identified contracts of Bancorp Financial contract in connection with the merger;

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holders of no more than 7.5% of the aggregate outstanding shares of Bancorp Financial common stock shall have properly notified Bancorp Financial of their intent to exercise dissenters’ rights under the applicable appraisal statutes;

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the execution by Darin Campbell of the Old Second officer agreements in the form attached to the merger agreement (and such individual must not have advised Old Second that he intends to breach any such agreement); and

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Bancorp Financial will have terminated its stockholders agreement prior to or as of the effective time of the merger.

Neither Old Second nor Bancorp Financial can provide assurance as to when or if all of the conditions precedent to the merger can or will be satisfied or waived by the appropriate party. As of the date of this proxy statement/prospectus, the parties know of no reason to believe that any of the conditions set forth above will not be satisfied.

#### Termination of the Merger Agreement
The merger agreement may be terminated at any time notwithstanding the approval of the merger agreement by the stockholders of Bancorp Financial, but not later than the effective time of the merger:

The merger agreement may be terminated prior to the effective time under the following