Company: OSBC
Filing Date: 2025-05-08
Form Type: 424B3
Source: 0001104659-25-046065
Chunk: 40

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-08
Form: 424B3
Chunk 40
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 obligations, covenants, and agreements required to be performed by it at or prior to the closing date of the merger; (j) 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; (k) 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 appraisal rights under the DGCL; and (l) the execution of the Old Second employment agreements by Darin Campbell in the form attached to the merger agreement.

These conditions to the closing of the merger may not be fulfilled in a timely manner or at all, and, accordingly, the merger may not be completed. In addition, the parties can mutually decide to terminate the merger agreement at any time, before or after stockholder approval, or Old Second or Bancorp Financial may elect to terminate the merger agreement in certain other circumstances. See “The Merger Agreement — Termination of the Merger Agreement” and “The Merger Agreement — Effect of Termination” beginning on pages 73 and 74, respectively.

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**TABLE OF CONTENTS

If Bancorp Financial stockholders do not approve the stockholders agreement amendment proposal, Bancorp Financial may be required to obtain individual written consents from stockholders holding at least 66**

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% of the outstanding common stock in order to amend and terminate the Stockholders Agreement, which could delay the completion of the merger.

Under the merger agreement, Bancorp Financial is obligated to use its best efforts to amend and terminate the Stockholders Agreement, which is a condition to closing the merger. Bancorp Financial is seeking stockholder approval of the stockholders agreement amendment proposal as a streamlined and coordinated means of satisfying this closing condition.

There can be no assurance that the stockholders agreement amendment proposal will receive the required affirmative vote of at least 66 2 ∕ 3 % of the outstanding shares of Bancorp Financial common stock. If the proposal is not approved at the special meeting, the alternative process of obtaining separate written consents could be time-consuming, uncertain, and may delay or jeopardize the timely completion of the merger.

Failure to complete the merger could negatively impact Old Second and Bancorp Financial.

If the merger is not completed for any reason