Company: OSBC
Filing Date: 2025-05-08
Form Type: 424B3
Source: 0001104659-25-046065
Chunk: 57

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-08
Form: 424B3
Chunk 57
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62 for additional and more detailed information regarding the legal documents that govern the merger, including information about the conditions to the completion of the merger and the provisions for terminating or amending the merger agreement.

### Background of the Merger
As part of its ongoing consideration and evaluation of its long-term prospects and strategies, Bancorp Financial’s board of directors and senior management regularly review and assess Bancorp Financial’s business strategies and objectives, including strategic opportunities and challenges, and consider various strategic options potentially available, with the goal of enhancing value for Bancorp Financial’s stockholders, and with consideration of the effects of such options on Bancorp Financial’s employees, customers and the communities in which its wholly owned banking subsidiary, Evergreen Bank Group, operates. These strategic discussions have focused on, among other things, the business, competitive and regulatory environment facing financial institutions generally, and Bancorp Financial in particular, as well as conditions and ongoing consolidation in the financial services industry. In addition, Bancorp Financial’s Chief Executive Officer received, from time to time, informal inquiries from representatives of other financial institutions about potential business combinations and Bancorp Financial’s board of directors has been regularly updated regarding these contacts.

Similarly, Old Second’s board of directors and senior management have from time to time engaged in reviews and discussions of long-term strategies and objectives and have considered ways to enhance Old Second’s performance and prospects in light of competitive, regulatory and other relevant developments, all with the goal of increasing long-term value for Old Second’s stockholders. For Old Second, these reviews have included periodic discussions with respect to potential transactions that would further its strategic objectives and the potential benefits and risks of any such transactions.

In addition, given its existing branch footprint in the Chicago MSA, Old Second is very familiar with the greater Chicagoland area, including Bancorp Financial and Evergreen Bank Group, which primarily

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operate from their office and branch locations in Cook County and DuPage County, Illinois. As a result, in late May 2024, James L. Eccher, Chairman, President and Chief Executive Officer of Old Second, contacted Darin Campbell, Chairman, President and Chief Executive Officer of Bancorp Financial, to set up an introductory meeting to discuss each party’s respective organization. In June 2024, Messrs. Eccher and Campbell met and discussed the current state of the banking industry generally, and also generally discussed each party’s operations.

In July 2024, in connection with the periodic review of its