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Old Second Bancorp director reports 22 acquisitions

The director's transactions were automatic dividend reinvestments in her IRA and had not been reported previously because of an administrative oversight.

(Neutral)

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Form Type
4

Rhea-AI Filing Summary

Old Second Bancorp Inc. director Jill E. York reported 22 direct acquisitions of common stock between May 11, 2021 and August 10, 2026. The shares came from automatic reinvestment of cash dividends in her individual retirement account through the account custodian; the acquisitions had not been reported earlier because of an administrative oversight. The latest acquisition was 12 shares at $25.38 on August 10, 2026. York also beneficially owned 15,430 shares through her living trust as of October 15, 2026.

Insider YORK JILL E
Role Director
Type Security Shares Price Value
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 11.8801 $25.38 $301.52
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.3767 $20.90 $300.47
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.1217 $21.21 $299.52
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 16.2619 $18.35 $298.41
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 15.3405 $16.61 $254.81
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 15.5779 $16.30 $253.92
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 13.3087 $19.02 $253.13
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 15.6156 $16.15 $252.19
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.0955 $14.86 $209.46
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.46 $14.43 $208.66
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 15.4522 $13.46 $207.99
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.5225 $14.27 $207.24
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 12.9172 $15.99 $206.55
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 18.4285 $11.16 $205.66
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 11.9166 $17.21 $205.08
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 12.0515 $16.97 $204.51
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.5777 $13.98 $203.80
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.3579 $14.14 $203.02
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.0252 $14.43 $202.38
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.5974 $13.81 $201.59
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 17.5446 $11.44 $200.71
Small Acquisition Old Second Bancorp, Inc. Common Stock F1, F2 14.2083 $14.08 $200.05
holding Old Second Bancorp, Inc. Common Stock F3 -- -- --
holding Restricted Stock Units -- -- --
Holdings After Transaction: Old Second Bancorp, Inc. Common Stock — 4,319.6382 shares (Direct); Old Second Bancorp, Inc. Common Stock — 15,430 shares (Indirect, Living Trust); Restricted Stock Units — 10,595 shares (Direct)
Footnotes (3)
  1. F1. Represents shares acquired through the automatic reinvestment of cash dividends paid on shares of the Issuer's common stock held in the Reporting Person's individual retirement account, under a dividend reinvestment feature offered by the account custodian. The custodian's reinvestment feature is not a plan sponsored by the Issuer. These acquisitions were not previously reported because of an administrative oversight, and are reported herein to correct the omission.
  2. F2. The amount of securities beneficially owned represents the Reporting Person's holdings in her individual retirement account as of the date hereof, after giving effect to all dividend reinvestment transactions reported herein. The transactions reported herein were not previously reported.
  3. F3. The Reporting Person additionally beneficially owns 15,430 shares through her living trust as of October 15, 2026. This amount reflects her current trust holdings and supersedes the trust balance previously reported.
Reported acquisitions 22 acquisitions Direct common-stock acquisitions from May 11, 2021 through August 10, 2026
Latest acquisition 12 shares August 10, 2026; rounded from 11.8801 shares
Price per share $25.38 Latest acquisition on August 10, 2026
Living trust holdings 15,430 shares As of October 15, 2026
dividend reinvestment feature financial
"under a dividend reinvestment feature offered by the account custodian"
individual retirement account financial
"shares of the Issuer's common stock held in the Reporting Person's individual retirement account"
A tax-advantaged retirement account owned by an individual that holds investments such as stocks, bonds, mutual funds or cash and is governed by rules about how much can be contributed and when money can be withdrawn. It matters to investors because the account’s specific tax rules and withdrawal limits affect how savings grow and when taxes are paid; think of it as a labeled box for retirement money that comes with special tax treatment and rules about when you can open it.
beneficially owns regulatory
"additionally beneficially owns 15,430 shares through her living trust"
Beneficially owns means a person or entity enjoys the economic benefits and control of a security even if the legal title or registration is held in another name. Think of it like having the keys and profits from a car that is registered to a friend: you use it, benefit from it, and make decisions about it even though the official paperwork lists someone else. For investors, this matters because it reveals who truly controls shares, affects voting power, potential conflicts of interest, and regulatory disclosure obligations.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

How many OSBC shares did Jill E. York acquire in her latest reported transaction?

York acquired 12 shares at $25.38 on August 10, 2026, through automatic reinvestment of cash dividends in her individual retirement account.

How were Jill E. York's OSBC share acquisitions made?

The shares were acquired through automatic reinvestment of cash dividends paid on common stock held in York's individual retirement account. The account custodian offered the reinvestment feature, which was not a plan sponsored by Old Second Bancorp.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
YORK JILL E

(Last)(First)(Middle)
37 S. RIVER ST.

(Street)
AURORA ILLINOIS 60506

(City)(State)(Zip)

UNITED STATES

(Country)
2. Issuer Name and Ticker or Trading Symbol
OLD SECOND BANCORP INC [ OSBC ]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirector10% Owner
Officer (give title below)Other (specify below)
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/11/2021
6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Old Second Bancorp, Inc. Common Stock05/11/2021L14.2083(1)A$14.084,319.6382(2)D
Old Second Bancorp, Inc. Common Stock08/11/2021L17.5446(1)A$11.444,319.6382(2)D
Old Second Bancorp, Inc. Common Stock11/09/2021L14.5974(1)A$13.814,319.6382(2)D
Old Second Bancorp, Inc. Common Stock02/08/2022L14.0252(1)A$14.434,319.6382(2)D
Old Second Bancorp, Inc. Common Stock05/10/2022L14.3579(1)A$14.144,319.6382(2)D
Old Second Bancorp, Inc. Common Stock08/09/2022L14.5777(1)A$13.984,319.6382(2)D
Old Second Bancorp, Inc. Common Stock11/08/2022L12.0515(1)A$16.974,319.6382(2)D
Old Second Bancorp, Inc. Common Stock02/07/2023L11.9166(1)A$17.214,319.6382(2)D
Old Second Bancorp, Inc. Common Stock05/09/2023L18.4285(1)A$11.164,319.6382(2)D
Old Second Bancorp, Inc. Common Stock08/08/2023L12.9172(1)A$15.994,319.6382(2)D
Old Second Bancorp, Inc. Common Stock11/07/2023L14.5225(1)A$14.274,319.6382(2)D
Old Second Bancorp, Inc. Common Stock02/06/2024L15.4522(1)A$13.464,319.6382(2)D
Old Second Bancorp, Inc. Common Stock05/06/2024L14.46(1)A$14.434,319.6382(2)D
Old Second Bancorp, Inc. Common Stock08/05/2024L14.0955(1)A$14.864,319.6382(2)D
Old Second Bancorp, Inc. Common Stock11/04/2024L15.6156(1)A$16.154,319.6382(2)D
Old Second Bancorp, Inc. Common Stock02/10/2025L13.3087(1)A$19.024,319.6382(2)D
Old Second Bancorp, Inc. Common Stock05/05/2025L15.5779(1)A$16.34,319.6382(2)D
Old Second Bancorp, Inc. Common Stock08/04/2025L15.3405(1)A$16.614,319.6382(2)D
Old Second Bancorp, Inc. Common Stock11/10/2025L16.2619(1)A$18.354,319.6382(2)D
Old Second Bancorp, Inc. Common Stock02/09/2026L14.1217(1)A$21.214,319.6382(2)D
Old Second Bancorp, Inc. Common Stock05/11/2026L14.3767(1)A$20.94,319.6382(2)D
Old Second Bancorp, Inc. Common Stock08/10/2026L11.8801(1)A$25.384,319.6382(2)D
Old Second Bancorp, Inc. Common Stock15,430(3)ILiving Trust
Restricted Stock Units10,595D
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Explanation of Responses:
1. Represents shares acquired through the automatic reinvestment of cash dividends paid on shares of the Issuer's common stock held in the Reporting Person's individual retirement account, under a dividend reinvestment feature offered by the account custodian. The custodian's reinvestment feature is not a plan sponsored by the Issuer. These acquisitions were not previously reported because of an administrative oversight, and are reported herein to correct the omission.
2. The amount of securities beneficially owned represents the Reporting Person's holdings in her individual retirement account as of the date hereof, after giving effect to all dividend reinvestment transactions reported herein. The transactions reported herein were not previously reported.
3. The Reporting Person additionally beneficially owns 15,430 shares through her living trust as of October 15, 2026. This amount reflects her current trust holdings and supersedes the trust balance previously reported.
/s/ Shirley Cantrell, Attorney-in-Fact10/21/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

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