Chilling with his colleagues at a nearby bar a few years back, the future CEO for the Tribune Company allegedly confused his waitress with a stripper, The New York Times reports.

Randy Michaels reportedly told his fellow senior corporate executives at the bar of the InterContinental Hotel -- next to the Tribune Tower -- to "watch this," before proceeding to offer the waitress $100 to show her breasts.

But that's not all...

Sam Zell, who purchased the Tribune in 2007, was 'handpicked' by Michaels, a former 'shock jock' and radio executive to head many of the company's holdings which included The Chicago Tribune, The Los Angeles Times, WGN America and The Chicago Cubs.

Perhaps bells and whistles should have sounded from the start, when Michaels and 20 former radio associates he appointed to key positions at the Tribune made rewriting of the employee handbook "one of their first priorities."

A giant red flag, and sign of things yet to come from the NYT:

“Working at Tribune means accepting that you might hear a word that you, personally, might not use,” the new handbook warned. “You might experience an attitude you don’t share. You might hear a joke that you don’t consider funny. That is because a loose, fun, nonlinear atmosphere is important to the creative process.” It then added, “This should be understood, should not be a surprise and not considered harassment.”

Carr's expose reveals just how unprofessional a 'loose, fun, nonlinear' atmosphere can be.

Announcing the new senior vice president of local sales in 2008, the Tribune's release said that Kim Johnson, a former Clear Channel executive was "a former waitress at Knockers — the Place for Hot Racks and Cold Brews," a jocular reference to a fictitious restaurant chain."

Tribune editor Ann Marie Lipinski, who resigned in under a year after Mr. Zell's takeover, tells Carr that Zell encouraged her to be harder on then-Illinois Governor Rod Blagojevich. Zell told her "Don't be a pussy." Lipinski learned that Zell was trying to sell Wrigley Field to the state, and pressure by the paper could be adventageous.

Editor and Publisher reports that Tribune CEO Randy Michaels who is "not one to sit and let such a story run in the Times without responding in kind, is trying to discredit Carr."

In a memo to Tribune staffers, first posted on Romenesko, the CEO writes, “Many of the questions Mr. Carr asked us for this article concerned events, distortions and rumors more than two years old. … Mr. Carr knows that an outside firm investigated the most substantial of these allegations, and that they were found to be without substance. Mr. Carr intends to use them anyway.”