Company: OSBC
Filing Date: 2025-04-23
Form Type: S-4
Source: 0001104659-25-037832
Chunk: 69

Company: OLD SECOND BANCORP INC
Filing Date: 2025-04-23
Form: S-4
Chunk 69
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 on the totality of the information presented to it and the factors it considered. In addition, individual members of the Bancorp Financial board of directors may have assigned different weights to different factors. The

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explanation of Bancorp Financial’s reasons for the merger includes statements that are forward-looking in nature and, therefore, should be read in light of the factors discussed above under “Cautionary Statement Regarding Forward-Looking Statements.”

The board of directors of Bancorp Financial unanimously recommends that Bancorp Financial stockholders vote “FOR” approval of the merger proposal, “FOR” approval of the stockholders agreement amendment proposal, and “FOR” approval of the adjournment proposal. Bancorp Financial stockholders should be aware that Bancorp Financial’s directors and executive officers have interests in the merger that are different from, or in addition to, those of other Bancorp Financial stockholders. The Bancorp Financial board of directors was aware of and considered these interests, among other matters, in evaluating and negotiating the merger agreement, and in recommending that the merger proposal be approved by the stockholders of Bancorp Financial. See “The Merger — Interests of Bancorp Financial Directors and Executive Officers in the Merger.”

### Opinion of Bancorp Financial’s Financial Advisor
Bancorp Financial engaged KBW to render financial advisory and investment banking services to Bancorp Financial, including an opinion to the Bancorp Financial board of directors as to the fairness, from a financial point of view, to the common stockholders of Bancorp Financial of the merger consideration in the proposed merger. Bancorp Financial selected KBW because KBW is a nationally recognized investment banking firm with substantial experience in transactions similar to the merger. As part of its investment banking business, KBW is continually engaged in the valuation of financial services businesses and their securities in connection with mergers and acquisitions.

As part of its engagement, representatives of KBW attended the meeting of the Bancorp Financial board of directors held on February 18, 2025, at which the Bancorp Financial board of directors evaluated the proposed merger. At this meeting, KBW reviewed the financial aspects of the proposed merger and rendered to the Bancorp Financial board an opinion to the effect that, as of such date and subject to the procedures followed, assumptions made, matters considered, and qualifications and limitations on the review undertaken by KBW as set forth in its opinion, the merger consideration (defined in KBW’s opinion as the per share cash consideration of $