Tribune, home to some of the most important newspapers in the country — The Baltimore Sun, The Hartford Courant and The Orlando Sentinel as well as The Chicago Tribune and The Los Angeles Times — had been battered by big drops in advertising and circulation. According to Mr. Zell, the company was also suffering from stodgy thinking and what he called “journalistic arrogance.”

“There’s a new sheriff in town,” he said, in speeches that were peppered with expletives, as he toured the Tribune’s offices.

It was a message that some within the company initially welcomed.

“Sam Zell was sort of a rock star when he went around and toured the various properties,” said Ann Marie Lipinski, the former editor of The Chicago Tribune who left less than a year after the takeover. “People had been living with uncertainty for so long and they hoped something good would come from an owner with a proven track record of success in other businesses.”

Mr. Zell’s first innovation was the deal itself. He used debt in combination with an employee stock ownership plan, called an ESOP, to buy the company, while contributing only $315 million of his own money. Under the plan, the company’s discretionary matching contributions to the 401(k) retirement plan for nonunionized Tribune employees were diverted into an ownership stake. The structure of the deal allowed Tribune to become an S corporation, which pays no federal taxes; its shareholders are responsible for all taxes.

The $8 billion in new loans used to finance the deal left the company with $13.8 billion in debt. But Mr. Zell was convinced that by quickly selling the Chicago Cubs and other assets while improving operating margins, the company could emerge as a valuable property. It was typical Zell: a risky approach to gain control over a large, distressed asset while minimizing his own exposure, something he acknowledged in a company newsletter:

“I’ve said repeatedly that no matter what happens in this transaction, my lifestyle won’t change,” he wrote to his combination employees/shareholders. “Yours, on the other hand, could change dramatically if we get this right.”

His second innovation was bringing in a new management team, largely from the radio business, that, like Mr. Zell, had little newspaper experience, which constituted more than 70 percent of the company’s business.

Mr. Michaels, who was initially in charge of Tribune’s broadcasting and interactive businesses as well as six newspapers, was a former shock jock who made a name for himself — and a lot of money for Mr. Zell — by scooping up radio stations while at the Zell-controlled Jacor Communications. Jacor was later sold to Clear Channel Communications for $4.4 billion.