Company: OSBC
Filing Date: 2025-05-06
Form Type: S-4/A
Source: 0001104659-25-045103
Chunk: 121

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-06
Form: S-4/A
Chunk 121
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 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, excluding any cash received in lieu of a fractional share of Old Second common stock (the tax treatment of which is discussed below), and (b) the excess, if any, of (i) the sum of the amount of such cash and the fair market value of the Old Second common stock received over (ii) the U.S. holder’s adjusted tax basis in the shares of Bancorp Financial common stock surrendered.

•

Any gain recognized generally will be capital gain, and will be long-term capital gain if, as of the effective date of the merger, the shares of Bancorp Financial common stock were held for more than one year, unless the receipt of cash has the effect of a distribution of a dividend under the provisions of the Code (