Company: OSBC
Filing Date: 2025-05-06
Form Type: S-4/A
Source: 0001104659-25-045103
Chunk: 407

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-06
Form: S-4/A
Chunk 407
---
 Court in and for DuPage County, Illinois and therefore submit to the personal jurisdiction of such courts. IN WITNESS WHEREOF, the parties have executed this Agreement to be effective as of the Effective Date.

| ​ | OLD SECOND BANCORP, INC. |   |   |                                  | ​ | ​ | DARIN CAMPBELL |   |   |   | ​ |
| ​ | By:                      | ​ | ​ | ​                                | ​ | ​ | By:            | ​ | ​ | ​ | ​ |
| ​ | ​                        | ​ | ​ | Chris Lasse, SVP Human Resources | ​ | ​ | ​              | ​ | ​ | ​ | ​ |
| ​ | Date:                    | ​ | ​ | ​                                | ​ | ​ | Date:          | ​ | ​ | ​ | ​ |

C-1-22

TABLE OF CONTENTS

#### Annex B​
February 18, 2025

The Board of Directors 
 Bancorp Financial, Inc. 
 1515 West 22 nd Street 
 Suite 100 West 
 Oak Brook, IL 60523

Members of the Board:

You have requested the opinion of Keefe, Bruyette & Woods, Inc. (“KBW” or “we”) as investment bankers as to the fairness, from a financial point of view, to the common stockholders of Bancorp Financial, Inc. (“Bancorp Financial”) of the Merger Consideration (as defined below) to be received by such stockholders in the proposed merger of Bancorp Financial with and into Old Second Bancorp, Inc. (“Old Second”) (such merger, the “Merger”), pursuant to the Agreement and Plan of Merger (the “Agreement”) to be entered into by and between Bancorp Financial and Old Second. Pursuant to the Agreement and subject to the terms, conditions and limitations set forth therein, at the Effective Time (as defined in the Agreement), by virtue of the Merger and without any action on the part of Old Second, Bancorp Financial or the stockholders of either of the foregoing, each share of the common stock, $1.00 par value per share, of Bancorp Financial (“Bancorp Financial Common Stock”) issued and outstanding immediately prior to the Effective Time (excluding the Canceled Shares and Dissenting Shares (each as defined in the Agreement)) shall be converted into the right to receive: (i) $15.93 in cash (the “Cash Consideration”)