Jeffrey Toobin Jeff Toobin CNN New Yorker.jpgWe recently wondered: Is Jeffrey Toobin the Tiger Woods of legal journalism? Like Tiger, he’s phenomenally talented and successful, the biggest name in the game. And, if news reports are correct, Toobin — a legal writer for the New Yorker, a political analyst for CNN, and the author of several bestselling books — may share Tiger’s weakness for women and wandering eye.

The big Jeff Toobin story is his alleged affair with Casey Greenfield, the daughter of political pundit Jeff Greenfield and an associate at Gibson Dunn. This romance resulted in a child that Toobin is allegedly refusing to support, according to Casey Greenfield — who just took Toobin to court over it.

Last weekend, the New York Daily News wrote about Toobin’s purported advances towards “a well-known media figure.” According to Rush and Molloy, Toobin made a proposition to this woman that was so crude as to be unprintable, even by the Daily News — and that’s saying something. (The folks at Gawker were less inhibited.)

So, who was the mystery media figure Toobin found so alluring?

Judith Regan HarperCollins editor publisher.jpgThe identity of the female media figure whom Jeffrey Toobin allegedly propositioned, through hotel room drop-bys and multiple dirty voice-mails? We hear it’s none other than Judith Regan (pictured), the notorious book editor and publisher who made her name cranking out lowbrow celebrity autobiographies. Apparently Regan has been telling tales about Toobin for years.

Judith Regan is no stranger to controversy or messy romances. She’s made headlines over the years for her affair with disgraced DHS nominee Bernard Kerik (recently sentenced to four years in prison), as well as her firing from HarperCollins (which she filed a $100 million lawsuit over, culminating in a settlement).

Given Regan’s affair with Kerik, her tabloid sensibility, and her generally unabashed nature, we’re surprised by the comment attributed to the media figure in the Daily News:

“At the time, I never even knew people did that.” O RLY? We could imagine such a “well I never” comment coming from, say, the bespectacled and endearingly awkward Linda Greenhouse. Judith Regan? Not so much.

Here’s a fun bit of possibly corroborating evidence regarding Toobin having a thing for Regan. Back in 2007, Rachel Sklar, another lawyer turned journalist, did a Thanksgiving piece for the Huffington Post asking noted media figures what they were thankful for. Here’s what Toobin said:

I know that Michael Vick is thankful for Larry Craig, who pushed Vick off the top of the news. Vick is thankful for Bernie Kerik for the same reason. And Kerik thanks Barry Bonds. And I, always, give thanks for Judith Regan.

Thanks for what? She denied you backdoor access, Jeff.

Perhaps this quip was an attempt by Toobin to flirt once again — publicly, yet slyly — with the elusive Regan. She’d get the joke, even if HuffPo readers wouldn’t.

Regan is assuredly attractive. But we still don’t understand why one would want to boldly go where one man, Bernie Kerik, has gone before. Ick.

P.S. Speaking of media figures and their affairs, Jeff Greenfield — the father of alleged Toobin baby mama Casey Greenfield, and Toobin’s former CNN colleague — has had some entanglements of his own. Some two decades ago, the marriage of noted political journalist and speechwriter Peggy Noonan hit the rocks because of an alleged affair with … Jeff Greenfield.
Noonan was romantically linked to Greenfield in 1990. At the time, Greenfield was married to Carrie Carmichael — Casey’s mother, whom he later divorced.

When will the vicious cycle of infidelity come to an end?

Happy Thanksgiving! ETP’s Favorite Media Mavens Give Thanks On This Holiday [Eat the Press / Huffington Post]
Too Hot For Print: CNN Anchor Jeffrey Toobin’s Rumored XXX Sex Fetish [Gawker]

Earlier: Is Jeffrey Toobin the Tiger Woods of Legal Journalism?
Legal Eagles Mate: But Who Will Take Care of the Eaglet?


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