Sun-Times Media Group Announces Court Approval of Settlement

Business Wire, May 27, 2008

CHICAGO -- Sun-Times Media Group, Inc. (Pink Sheets: SUTM) today announced that it has received approval from a Canadian court of a settlement agreement that will resolve the various disputes and litigation among the Company, its controlling shareholder, Hollinger Inc. and Hollinger's largest secured noteholder, Davidson Kempner Capital Management LLC.

Ontario Superior Court Judge Colin Campbell on May 26, 2008 approved the settlement agreement under the Canadian Companies' Creditors Arrangement Act. The settlement agreement was announced on March 25, 2008, and revised on May 14, 2008. The court's approval will result in the automatic conversion of all of Hollinger Inc.'s outstanding Class B shares to Class A shares, the elimination of 10-to-1 voting rights held by Hollinger Inc. and the issuance of 1.499 million Class A shares to Hollinger Inc., and implementation of other terms of the agreement, which were previously announced. The Company expects that implementation of all settlement terms will be completed before its next regularly scheduled annual shareholders meeting on June 17, 2008, except for the resignations of certain directors, which will occur immediately after the annual meeting.

"We are very pleased to have resolved this complicated matter," said Cyrus F. Freidheim, Jr., President and Chief Executive Officer of Sun-Times Media Group. "This is another step in achieving the goals we have laid out to our shareholders: improved operating performance, resolution of the Company's unique legacy issues, and exploration of strategic alternatives for the Company."

About Sun-Times Media Group

Sun-Times Media Group is dedicated to being the premier source of local news and information for the greater Chicago area. Its media properties include the Chicago Sun-Times and Suntimes.com as well as newspapers and Web sites serving more than 200 communities across Chicago. Further information can be found at www.thesuntimesgroup.com.

Cautionary Statement on Forward-Looking Statements

Certain statements made in this release are "forward-looking statements" within the meaning of the Private Securities Litigation Reform Act of 1995 (the "Act"). Forward-looking statements include, without limitation, any statement that may predict, forecast, indicate or imply future results, performance or achievements, and may contain the words "believe," "anticipate," "expect," "estimate," "project," "will be," "will continue," "will likely result" or similar words or phrases. Forward-looking statements involve risks and uncertainties, which may cause actual results to differ materially from the forward-looking statements. The risks and uncertainties are detailed from time to time in reports filed by Sun-Times Media Group with the Securities and Exchange Commission, including in its Forms 10-K and 10-Q. New risk factors emerge from time to time and it is not possible for management to predict all such risk factors, nor can it assess the impact of all such risk factors on the Company's business or the extent to which any factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements. Given these risks and uncertainties, investors should not place undue reliance on forward- looking statements as a prediction of actual results.