Company: OSBC
Filing Date: 2025-05-08
Form Type: 424B3
Source: 0001104659-25-046065
Chunk: 120

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-08
Form: 424B3
Chunk 120
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 as applicable, and on customary factual assumptions, including, but not limited to, the assumption that the merger will be consummated in accordance with the terms of the merger agreement. If any of the representations or assumptions upon which those opinions are based is incorrect or incomplete, the validity of the opinions may be affected and the tax consequences of the merger could differ from those described in this proxy statement/prospectus. None of these opinions of counsel, including the opinions delivered in connection with the filing of this Registration Statement on Form S-4 of which this proxy statement/prospectus forms a part, is binding on the IRS or any court. No ruling has been, or will be, sought from the IRS by Old Second or Bancorp Financial as to the U.S. federal income tax consequences of the merger, and as a result, there can be no assurance that the IRS will not assert, or that a court would not sustain, a position contrary to any of the conclusions set forth herein. Accordingly, each holder of Bancorp Financial common stock should consult its own tax advisor with respect to the particular tax consequences of the merger to such holder.

Based solely on the information, and subject to the assumptions, qualifications and limitations set forth herein and in their respective federal income tax opinions filed herewith, it is the opinion of Nelson Mullins Riley & Scarborough LLP and Vedder Price P.C. that the merger will qualify as a reorganization within the meaning of Section 368(a) of the Code for U.S. federal income tax purposes and that accordingly the material U.S. federal income tax consequences of the merger generally applicable to U.S. holders of Bancorp Financial common stock who exchange their shares of Bancorp Financial common stock for the merger consideration pursuant to the merger will be those set forth in this section entitled “Material U.S. Federal Income Tax Consequences of the Merger.”

### Tax Consequences to Old Second and Bancorp Financial
Each of Old Second and Bancorp Financial will be a party to the merger within the meaning of Section 368(b) of the Code, and neither Old Second nor Bancorp Financial will recognize any gain or loss as a result of the merger.

### Tax Consequences to Bancorp Financial Stockholders
The material U.S. federal income tax consequences of the merger to U.S. Holders who exchange Bancorp Financial common stock for merger consideration are as follows:

•

A U.S. holder will recognize gain, but not loss, in an amount equal to the lesser of (a) the amount of cash received,