Judith Regan on Millionaire Matchmaker, NewsCorp. and Her Love Life

Even by Judith Regan’s over-the-top standards, it has been a very rough year.

Her beloved younger sister, Patricia, an artist and mother of two, died at 50 after decades of suffering from multiple sclerosis. Regan is being chased by litigious bankruptcy creditors somehow connected to a crooked lawyer she once hired. And her Soho apartment flooded—twice—ruining nearly all her art and furniture—twice.

“It’s a great apartment, a fabulous apartment,” she tells me over breakfast at Manhattan’s Balthazar restaurant, a short stroll from her water-damaged 3,200-square-foot loft. “I have sweeping views of the Brooklyn Bridge, the Empire State Building. And the ceilings are almost as high as these,” she adds, casting her eyes heavenward to Balthazar’s cavernous ceiling. “My apartment is like all the men in my life—really good-looking and assholes."

As for Regan’s love life—which once was the stuff of tabloid headlines, the outcome of an affair-gone-wrong with the now-imprisoned ex-New York police commissioner, Bernard Kerik—well, put it this way: The onetime Queen of All Media is going on The Millionaire Matchmaker.

“Why not? I just thought it could be a hoot,” says the Sirius XM radio host, and once and possibly future publishing powerhouse, “I did it because it’s so ridiculous and so outrageous—but all of life is that way now. That’s the way the culture is. That’s the way everything is.”

The 57-year-old Regan, who was famously fired from her ReganBooks imprint at HarperCollins by News Corp. chief Rupert Murdoch in 2006 (ostensibly for publishing the reviled O.J. Simpson’s conditional mea culpa If I Did It, resulting in a hornet’s nest of recrimination, litigation, and a fat multimillion-dollar settlement for Regan) is a vision in purple. She’s wearing a purple blazer over a purple silk blouse—and speaking in purple prose.

“It’s all about humiliation,” she tells me about the hit Bravo show. “ ‘Let’s humiliate the millionaire!’ The whole conceit of the show is that millionaires are all flawed and that’s why they can’t find love relationships. Because rich people are bad—they’re all evil. But I tried to give them as few opportunities as I could to edit it and to make me the most miserable bitch on earth.

“My apartment is like all the men in my life—really good-looking and assholes,” Regan says.

By contractual agreement, Regan can say very little about her episode, which was filmed last summer and airs December 14, but she clearly met her match in reality-TV star Patti Stanger, a frequent guest on her radio show who has been nagging her for the past year to go on camera as a lovelorn rich lady.

“I told her, ‘I’m retired, I’m not interested,’” Regan recounts. “‘Well there must be some guy.’ I said, ‘Look, the perfect man for me at this point of my life is a cross between Zach Galifianakis and Bruce Vilanch. Because I need someone with wit and charm, who makes me laugh—and that’s it.’ But Patti’s orientation is all ‘you have to have sex.’ I don’t think she understands that for me, it’s not all about sex, because I’ve had a lot of sex. I don’t care anymore. It’s not Numero Uno on my list anymore."

In the middle of filming, Regan says, she ran into Stanger in the ladies' room. “She talks a mile a minute. You can’t really have a conversation with Patti. You just listen,” Regan says. “So she pulls me aside and says, ‘This is for TV, blah blah blah, but I actually have the perfect guy for you.’ I’d just finished telling her that what I want more than anything in a man is wit. She leans over and says, ‘This one will love you. You are sooo his type. I’ve been setting him up for years. He is just the most perfect guy, and he buys all of his women the best lingerie. You’re sooo gonna love him. And his name is Sumner Redstone!' "

Regan bursts out laughing at the memory of Stanger attempting to mate her with the 87-year-old executive chairman of Viacom and CBS—who is renowned for a lot of things, but not his wit. “This is the perfect man for me, according to Patti Stanger,” Regan says. “She has a vivid imagination. And she lives in a fantasy world—it’s a beautiful fantasy world. And then she says to me, ‘Much better than Rupert Murdoch!' "

Any mention of Murdoch is apt to provoke Regan into a lengthy and detailed indictment of the media mogul’s alleged treachery against her after she made so much money for him. I manage, with some effort, to discourage this. Still, her bloody combat with her former employer was the epic battle of a lifetime. She takes perverse pride in having enemies—the right enemies—and won’t be silenced.

“Most people roll over,” she explains. “Most people don’t have the fight in them, don’t have the courage and the conviction. They just don’t. And I really don’t have the disposition to tolerate what I feel is an injustice. Because, strangely, I’m not really materialistic—so I’ll fight to the death."

Warming to her subject, Regan goes on, “I’ve had to fight for everything. Nobody gave me anything. I strongly believe that I’m right. And if you strongly believe you’re right and you’ve been wronged, then what’s your choice? I was very wronged by News Corp., and they had to retract all the bullshit they said and they had to eat it, and they had to pay me. You have to give me credit: I did win in the end."

Regan—who made Howard Stern, Rush Limbaugh, and Jenna Jameson, among others, bestselling authors—was so legendary in the publishing business for what many saw as her larger-than-life, foul-mouthed, unreasonably demanding personality that former ReganBooks editor Bridie Clark wrote a thinly veiled novel about her, titled Because She Can.

“Ridiculous, and, by the way, a terrible novel,” Regan snorts. “She was a terrible mini-baby editor, and she’s a terrible writer. What can I tell you, a woman of no talent.” Clark declined an opportunity to respond.

As for HarperCollins, and its former Chief Executive Jane Friedman, who played a role in Regan’s termination, “They were foolish enough to let Chelsea Handler [a ReganBooks author] go, and her book became the No. 1 bestseller that Simon & Schuster had,” Regan says. “But Jane Friedman decided to let it go. Stupid. Nyah nyah nyah nyah!” Friedman, too, had no comment.

And Regan is withering about Glenn Beck, whom she accuses of “repulsive anti-Semitism,” a problem she says Beck shares with Fox News in general.

“They specialize in it—look what they’ve done to George Soros. It’s unbelievable,” says Regan, who at one point in her battle with Murdoch was accused by News Corp. lawyers of making anti-Semitic remarks—a claim they later retracted. “If you study the Fox News method of operation, there’s all kinds of historic anti-Semitic views and the stuff with Glenn Beck is textbook.” A Fox News spokesman also refused to join the battle.

Regan says she’s used to being dismissed. “It’s ‘Oh, Judith is crazy, Judith is a bitch, Judith is this, Judith is that’—the name-calling, the defamation, all the stuff I’ve been through a thousand and one times, same old, same old, same old,” she says.

Yet, despite all the above, Regan doesn’t sound bitter, just filled with righteous rage. And she softens when she speaks about her kids from two different “inseminators,” as she calls her exes—19-year-old Lara, a college student, and 30-year-old Patrick, a married entrepreneur who is marketing a specialty iPad case. And Regan is also enthusiastic about one of her most important associations.

“I never endorse anything ever, ever, ever, ever!” Regan says. “I hate everybody and everything. As a general rule, I’m very hard to please. But I have one word to say to you. Are you ready? Chubb!"

Chubb?

“Chubb Insurance! Seriously, if you ever deal with Verizon or Time Warner, or if somebody steals your American Express card, what you have to go through to prove this, do that, it’s horrifying. It’s almost impossible to get people to honor their commitments. Everything is a nightmare. Except for Chubb. Chubb is the healthiest relationship I have in my life. I want to marry Chubb!"

She’s kidding, of course. At least I think she’s kidding.

Lloyd Grove is editor at large for The Daily Beast. He is also a frequent contributor to New York magazine and was a contributing editor for Condé Nast Portfolio. He wrote a gossip column for the New York Daily News from 2003 to 2006. Prior to that, he wrote the Reliable Source column for the Washington Post, where he spent 23 years covering politics, the media, and other subjects.