Charlie Sheen's Longtime Publicist Stan Rosenfield Resigns

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The Times pointed to an example from 2006, when DeVito showed up on the set of "The View," slurring his speech and rambling incoherently. DeVito freely admitted to the co-hosts that he'd been out partying with George Clooney the night before, saying, "I knew it was the last seven limoncellos that was going to get me."

Charlie Sheen's Publicist Quits

But when asked about his client, Rosenfield insisted that he had "no idea" whether DeVito was drunk during his "View" appearance. Instead he emphasized that the actor had never had a drinking problem.

With Sheen, Rosenfield seemed to be in difficult position, caught between protecting his client and enabling his bad behavior.

"All you can do in situations like this is help make things less bad. It is nearly impossible to manage a personality like this because their fundamental objective is to keep misbehaving and having others clean up after them," said Eric Dezenhall, a Washington, D.C.-based crisis management expert who is author of the book, "Damage Control."

"One of the reasons I don't like celebrity cases is that these folks are surrounded by people who enable them rather than tell them to shape up," Dezenhall said. "Tough love usually means you're out of a job."

That's one risk Bragman said he would be willing to take, because he knows the consequence of not doing so.

"I had a client who died of an overdose on my watch and I will never let that happen again," he said. "It's one of the saddest memories I have of my entire career."

If Sheen were his client, Bragman said, "I would draw a line in the sand and say, 'Charlie, you need help or I can't be at your side, because I can't let this happen during my watch.'"

Apparently, Rosenfield had finally reached that line.

Watch much more of the ABC News interview with Charlie Sheen Tuesday on "GMA" at 7 a.m. ET and on a special one-hour edition of "20/20" Tuesday at 10 p.m. ET.

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