In January 2008, soon after the venerable Tribune Company was sold for $8.2 billion, Randy Michaels, a new top executive, ran into several other senior colleagues at the InterContinental Hotel next to the Tribune Tower in Chicago.
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.
“Here was this guy, who was responsible for all these people, getting drunk in front of senior people and saying this to a waitress who many of us knew,” said one of the Tribune executives present, who declined to be identified because he had left the company and did not want to be quoted criticizing a former employer. “I have never seen anything like it.”
Mr. Michaels, who otherwise declined to be interviewed, said through a spokesman, “I never made the comment allegedly attributed to me in January 2008 to a waitress at the InterContinental Hotel, and anyone who said I did so is either lying or mistaken.”
It was a preview of what would become a rugged ride under the new ownership. Mr. Zell and Mr. Michaels, who was promoted to chief executive of the Tribune...