CHICAGO (AP) - Conrad Black took a parting shot at those running his old newspaper company as he received a six-and-a-half-year prison sentence this week, citing the "evaporation" of $1.85 billion of shareholder value since he was ousted.

The remark rankled some victimised ex-shareholders of the former Hollinger International, given that the disgraced media baron was convicted of swindling the company, while resonating with at least a few unhappy current investors.

But it served to underscore the ongoing struggles of the remnants of his one-time empire, Sun-Times Media Group Inc., now striving to return to profitability amid bleak industry conditions and facing a potential sale or breakup as soon as 2008.

Operating losses are mounting, revenues remain in free fall, and print advertising and circulation continue to sink. The Chicago-based company's share price, which closed at $15.77 on Black's last day as CEO on November 21, 2003, fell to 85 cents earlier this month and closed yesterday at $1.14 - collapsed under a mountainous burden of scandal, legal expenses and other problems.

"They were left in a mess by Lord Black," said George Putnam, editor of The Turnaround Letter for investors and president of Boston-based New Generation Advisers, which owns nearly 1.5 million shares of the company. "It's taking time to straighten it out."

At its peak in the late 1990s, the Hollinger International newspaper empire included The Daily Telegraph of London, the Jerusalem Post, the Toronto-based National Post, the Chicago Sun-Times and close to 500 smaller US and Canadian publications. All that's left is the Sun-Times and dozens of community papers in the metropolitan area.

Britain's Barclay brothers offered Mr. Black $17.43 a share for the then-larger company in 2004 - a deal that was blocked by a Delaware judge after questions emerged about millions of dollars he pocketed from newspaper sales.

Today, Sun-Times Media is not even considered suitable for sale until it completes a drastic overhaul.

Chief executive Cyrus Freidheim has been heading a cost-slashing restructuring since taking over at the end of 2006, with virtually the entire senior management team turning over in the past 13 months. But the turnaround effort has been slow to show results. Last month, the company reported a widened third-quarter loss of $192.4 million on a seven percent drop in revenue.

"Not unlike its neighbors at Tribune Co., the management team has had significant distractions while facing the enormous challenge of trying to adapt its business to reflect the shift of advertising dollars toward online and other emerging mediums," said Mike Simonton, an analyst for Fitch Ratings.

"They've tried to be aggressive on costs, but in the third quarter the five percent they took out didn't offset the seven percent decline in revenue."

Some institutional investors are growing increasingly impatient.

K Capital Management, which owns nearly 10 percent of Sun-Times stock, urged the company in a letter this week to move faster and set targets that will lead to its sale within a year. The Boston-based firm has seen its 6.4 million shares decline in value from $33.7 million on June 30 to only about $7 million.

Abner Kurtin, K Capital's chief investment officer, maintains that the current board's performance is worse than it was under Mr. Black.

"The bottom line is these are high-quality assets that have been mismanaged by a distracted and incompetent board," he said in an interview. "If the current management can't fix it within 12 months, they will sell to industry buyers who can realise value."

Mr. Putnam is more supportive, saying management is "doing all the right things." He said there's a "reasonable" possibility that the company will either get turned around or merge with a stronger firm.

Many of the distractions are linked to litigation. Sun-Times Media is digging out from the aftermath of almost $200 million in legal fees and other liabilities related to Mr. Black and his longtime partner in the newspaper business, F David Radler, who faces a 29-month sentence for mail fraud.

Shareholder Eugene Fox took issue with Mr. Black's comment directing blame at his successors ruining the company. Fox, managing director of Connecticut-based Cardinal Capital Management said at Mr. Black's sentencing on Monday that "the financial portion of the Sun-Times Media Group has been significantly burdened by the defendant's legacy."

Just the costs of defending Mr. Black alone came to nearly $108 million, not counting other costly consequences of his legacy.

The legal battles could not have come at a worse time for the company, squeezed like others by the historic slump in the newspaper industry reflecting an exodus of advertisers and readers to the Internet.

Besides resolving some of its legal problems this year, the company has reduced its staff by more than 10 percent, outsourced non-core jobs, cut other costs aggressively and restructured its newsrooms to focus on the Internet first. But the company is still waiting for the results to bring improvement.

Tammy Chase, Sun-Times' director of investor relations, declined to comment on Mr. Black or the turnaround plan but said the company is "focused on the future."