Company: OSBC
Filing Date: 2025-05-08
Form Type: 424B3
Source: 0001104659-25-046065
Chunk: 121

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-08
Form: 424B3
Chunk 121
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 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.

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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 (as discussed below), in which case such gain will be treated as dividend income to the extent of the U.S. holder’s ratable share of Bancorp Financial’s current and accumulated earnings and profits as calculated for U.S. federal income tax purposes.

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In general, the determination of whether any gain recognized will be treated as capital gain or a dividend distribution will depend on whether, and to what extent, the merger reduces the U.S. holder’s deemed percentage stock ownership in Old Second, taking into account certain constructive ownership rules. The IRS has indicated in rulings that any reduction in the interest of a stockholder that owns a small number of shares in a publicly and widely held corporation and that exercises no control over corporate affairs would result in capital gain as opposed to dividend treatment.

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Because the possibility of dividend treatment depends primarily upon a U.S. holder’s particular circumstances, including the application of constructive ownership rules, U.S. holders should consult their tax advisors regarding this possibility.

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A U.S. holder generally will have an aggregate tax basis in the shares of Old Second common stock received by the U.S. holder in the merger (including any fractional share of Old Second common stock deemed received and redeemed for cash, as discussed below) equal to the U.S. holder’s aggregate adjusted tax basis in the shares of Bancorp Financial common stock surrendered, reduced by the amount of cash received (other than cash received in lieu of a fractional share of Old Second common stock), and increased by the amount of any gain recognized or amount treated as a dividend by the U.S. holder (excluding any gain recognized with respect to cash received in lieu of a fractional share of Old Second common stock).

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The holding period of the shares of Old Second common stock received by