Did Tribune Co. CEO Randy Michaels really offer to pay a waitress at the InterContinental Hotel bar $100 to show him her breasts?

Through a spokesman, Michaels denied it happened. But a report Wednesday in The New York Times cites two witnesses who were present that night in January 2008 when Michaels allegedly made the comment before several senior executives of the company. The hotel at 505 N. Michigan Ave. is located next door to Tribune Tower.

“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,” the newspaper quoted one of the executives as saying. “I have never seen anything like it.”

The incident is just one of numerous horror stories recounted in a scathing investigation of Tribune Co. under the ownership of Sam Zell. Noting that more than 4,200 people have lost their jobs and that resources for the company’s newspapers and television stations have been slashed since Zell bought the company, reporter David Carr details a disturbing transformation in the work culture under Zell and Michaels:

“Based on interviews with more than 20 employees and former employees of Tribune, Mr. Michaels’s and his executives’ use of sexual innuendo, poisonous workplace banter and profane invective shocked and offended people throughout the company. Tribune Tower, the architectural symbol of the staid company, came to resemble a frat house, complete with poker parties, juke boxes and pervasive sex talk.”

Readers of this blog already know all about the drinking, smoking and gambling party Michaels hosted for his management pals in the former office of Col. Robert R. McCormick, the company’s patriarch. Reporter Carr puts that incident and others in the context of a company in financial and moral bankruptcy. Among sources he quotes:

• Newspaper industry analyst Ken Doctor: “They threw out what Tribune had stood for, quality journalism and a real brand integrity, and in just a year, pushed it down into mud and bankruptcy. And it’s been wallowing there for the last 20 months with no end in sight.”
• Former Tribune managing editor James Warren: “They wheeled around here doing what they wished, showing a clear contempt for most everyone that was here and used power just because they had it. They used the notion of reinventing the newspapers simply as a cover for cost-cutting.”
• Los Angeles Times columnist Steve Lopez: “You have advertising wrapping around sections and being disguised as news and empty desks all around you, and then you read about these ridiculous bonuses and feathering their nests with severances, you want to scream.”
• Former WGN-AM (720) personality Steve Cochran: “[Radio] was supposed to be their comfort zone, what they were good at, and they have ruined a radio station that has had an 80-year relationship with its listeners. This is a collection of carnival workers who are only looking after their friends, giving jobs to their buddies. Blagojevich is on trial and you bring in a politician [Jim Laski] who has done time in jail?”

Update: Phil Rosenthal quotes Randy Michaels’ email to employees about David Carr and The New York Times’ report.)