If you haven't read Clegg's memoir, allow me to summarize: for reasons that aren't made entirely clear, Bill Clegg decides to throw away his relationship with his family, flagrantly cheat on his live-in boyfriend, and abandon his career (deserting his pregnant business partner and dozens of clients in the process) so he can blow through $70,000 worth of savings smoking crack. (He relapses or drops out of rehab more than once.) Clegg portrays himself as not very nice and not overwhelmingly intelligent, though he does (pre-crack binge, at least) sound funny and fairly charming. That aside, however, he sounds like someone of whom I wouldn't even want to be a friend of a friend of a friend, much less someone I'd want to work with. (Full disclosure: I have never met Bill Clegg in real life.)
Here's the kicker, though: after he finally cleaned up his act, Clegg—who never actually apologized to the the aforementioned abandoned business partner—didn't seem to suffer at all from having burnt nearly every bridge he had. He not only got a pretty cushy job with William Morris Endeavor Entertainment, but even got many of his former clients back. Clients he had abandoned with no explanation so he could smoke a bunch of crack, drink liver-brittling amounts of room service vodka, and have sex with $400/hour prostitutes.
Granted, this is far and away an outlier in the Realm of Recorded Agent Behaviors, but I think it warrants attention not only because of Clegg's high profile, but because of the relative lack of professional repercussions he seems to have suffered.
This might be an easy one, but prithee, inform me: would you have gone back to an agent like Bill Clegg if you believed (s)he were the best fit for your work and/or would get you the best deal available? What would and wouldn't you tolerate in a relationship with your agent?