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New York's Worst Bosses: Barry Diller

With your help, we've ID'd some of the potentially worst bosses in New York. We'll be parading them in front of you daily, and when we're done, we'll all decide together who's the worst. Feel free to shout out your suggestions if any of these tales joggles a traumatized (or happy) memory!

InterActiveCorp CEO Barry Diller is one of the people we'd initially thought too obvious to include on this list, which is supposed to be for small-time bad bosses, not the legends. And if there's one thing Diller's not, it's small-time: the man raked in $469 million in the 2005-2006 fiscal year, prompting Nick Kristof to award him the not-coveted Michael Eisner award for laziness and corporate rapacity. Diller called critics of his pay package "birdbrains." He really likes the word birdbrain! But that's not why he's included in this roundup.

The intriguing thing about Diller is how many emails we got—lots!—that said, essentially, 'Barry Diller is the worst boss, please investigate' or some other detail-free variation on that theme. In fact, some tipsters seemed leery of even spelling out Diller's full name.

Perhaps a number of them have signed some nondisclosure agreements. Or maybe they're just too shellshocked to speak? Our least-terse (but still pretty terse!) tipster indicated that this is the case, citing PTSD-like symptoms: nightmares, unbidden flashbacks. Literally. One former employee reports stopping on the street sometimes and losing himself in recollection of horrors past.

But is it PTSD that's keeping former employees from speaking out, or something more akin to Stockholm Syndrome? That same tipster is careful to mention that Diller "does often come through with an apology or act of graciousness." Maybe, behind his famed impatience and bluster he's actually sort of a nice guy after all—how tough can someone who calls Diane Von Furstenberg "cabbage" be, anyway?

Clearly we'll never know, though, if someone doesn't speak up. —Emily


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