UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

FORM 144
NOTICE OF PROPOSED SALE OF SECURITIES
PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933

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OMB Number: 3235-0101

Expires: December 31, 2009

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SEC USE ONLY

DOCUMENT SEQUENCE NO.

CUSIP NUMBER

ATTENTION:

Transmit for filing 3 copies of this form concurrently with either placing an order with a broker to execute sale or executing a sale directly with a market maker.

1 (a) NAME OF ISSUER (Please type or print)

(b) IRS IDENT. NO.

(c) S.E.C. FILE NO.

WORK LOCATION

Old Second Bancorp, Inc.

36-3143493

000-10537

1 (d)

ADDRESS OF ISSUER

STREET

CITY

STATE

ZIP CODE

(e) TELEPHONE NO.

37

S. River St.

Aurora

IL

60506

AREA
CODE

NUMBER

630

892-0202

2 (a)

NAME OF PERSON FOR WHOSE ACCOUNT THE SECURITIES ARE TO BE SOLD

(b)

IRS IDENT. NO.

(c)

RELATIONSHIP TO ISSUER

(d)

ADDRESS STREET

CITY

STATE

ZIP CODE

James C. Schmitz

Director

C/o Old Second Bancorp, Inc.

37 S. River St.

Aurora

IL

60506

3 (a)

Title of the Class of Securities To Be Sold

(b)

Name and Address of Each Broker Through Whom the Securities are to be Offered or Each Market Maker who is Acquiring the Securities

SEC USE ONLY

(c)

Number of Shares
or Other Units
To Be Sold
(See instr. 3(c))

(d)

Aggregate
Market
Value
(See instr. 3(d))

(e)

Number of Shares
or Other Units
Outstanding
(See instr. 3(e))

(f)

Approximate Date of Sale
(See instr. 3(f))
(MO. DAY YR.)

(g)

Name of Each Securities Exchange
(See instr. 3(g))

Broker-Dealer
File Number

Old Second Bancorp Inc.

Weeden & Co

30,000 shares

Sales will be based on market value on date of sale

13,761,218

01-29-09

Nasdaq

1.

(a)

Name of issuer

3.

(a)

Title of the class of securities to be sold

(b)

Issuer’s I.R.S. Identification Number

(b)

Name and address of each broker through whom the securities are intended to be sold

(c)

Issuer’s S.E.C. file number, if any

(c)

Number of shares or other units to be sold (if debt securities, give the aggregate face amount)

(d)

Issuer’s address, including zip code

(d)

Aggregate market value of the securities to be sold as of a specified date within 10 days prior to the filing of this notice

(e)

Issuer’s telephone number, including area code

(e)

Number of shares or other units of the class outstanding, or if debt securities the face amount thereof outstanding, as shown by the most recent report or statement published by the issuer

(f)

Approximate date on which the securities are to be sold

2.

(a)

Name of person for whose account the securities are to be sold

(g)

Name of each securities exchange, if any, on which the securities are intended to be sold

(b)

Such person’s I.R.S. identification number, if such person is an entity

(c)

Such person’s relationship to the issuer (e.g., officer, director, 10% stockholder, or member of immediate family of any of the foregoing)

(d)

Such person’s address, including zip code

Title of the Class

Date you Acquired

Nature of Acquisition Transaction

Name of Person from Whom Acquired
(If gift, also give date donor acquired)

Amount of Securities Acquired

Date of Payment

Nature of Payment

Old Second Bancorp Inc

01/07/02

Acquired through inheritance

J. Carl Schmitz Marital Trust and

J. Carl Schmitz Residual Trust

40,000

N/A

N/A

INSTRUCTIONS:

If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Name and Address of Seller

Title of Securities Sold

Date of Sale

Amount of Securities Sold

Gross Proceeds

N/A

INSTRUCTIONS:

ATTENTION:

See the definition of “person” in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed.