Mr. Michaels, a former radio executive and disc jockey, had been handpicked by Sam Zell, a billionaire who was the new controlling shareholder, to run much of the media company's vast collection of properties, including The Chicago Tribune, The Los Angeles Times, WGN America and The Chicago Cubs.
After Mr. 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.
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