In January 2008, soon after the venerable Tribune Co. was sold for $8.2 billion, Randy Michaels, a new top executive, ran into several other senior colleagues at the InterContinental Hotel next to Tribune Tower in Chicago.

Michaels, a former radio executive and disc jockey, had been handpicked by Sam Zell, a billionaire who was the new controlling shareholder. After Michaels arrived, according to two people at the bar that night, he sat down and said, “watch this,” and offered the waitress $100 to show him her breasts. The group sat dumbfounded.

It was a preview of what would become a rugged ride under the new ownership for the parent of the Los Angeles Times and KTLA-TV, according to interviews with more than 20 employees and former employees of Tribune.

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