It Wasn’t Worth It: History’s Most Embarrassing Mistresses

Judging from recent headlines about former New York Mets GM turned ESPN analyst Steve Phillips—who was suspended after dumping Brooke Hundley, the assistant he’d had an affair with—finding a good girl on the side just isn’t easy anymore. The tubby temptress started writing letters to brag about their sexual encounters, impersonating his children’s classmates, and even warning Mrs. Phillips, “We both can’t have him!”

At the end of the day, it’s Stevie’s fault for picking such a crazy, unattractive co-worker as his jumpoff. Would it have been any better if he had bedded a slammin’ super-rich supermodel? Maybe not for his wife, but at least we could understand it. Take a look back at the history of other celebrities who made us wonder, Why’d you risk it all for her?

NAME: Prince Charles
MISTRESS: Camilla Parker-Bowles
COMPLEX SAYS: Princess Diana probably already knew the deal when Prince Charles claimed Camilla as a “close acquaintance,” and was found sleeping with her in a train the night before his wedding. Who knows what went down, but fast forward to present day and he can still be found with Parker-Bowles.
WORTH IT? No. He has Royal blood and that’s who he fell in love with? Come on, Charles you were married to an actual Princess.

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NAME: David Letterman
MISTRESS: Stephanie Birkitt
COMPLEX SAYS: From intern to producer to extortionist chick…What a catch! Having her own share of air-time throughout shows, Birkitt’s known as Letterman’s perky sidekick, on and off the camera. Perky enough that one of his nicknames for her was “Smitty.”
WORTH IT? No. Dave’s act made him lose out on all other potential sex-capades with hotter chicks during commercial breaks.

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NAME: Jesse Jackson
MISTRESS: Karin Stanford
COMPLEX SAYS: Former PUSH (People United to Save Humanity) staffer turned baby-moms, Karin was Jackson’s extra-marital interest to whom he now is legally obligated to fork over money for every month. The ironic part? Jackson had his affair as he counseled former President Bill Clinton on his infidelity.
WORTH IT? No. Jesse has anywhere from 8-11 years left on his payment plan.

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NAME: Bill Clinton
MISTRESS: Monica Lewinsky
COMPLEX SAYS: Bill is no stranger to the playa’s club—his long history of jumpoffs should have been enough to give him a verse on 50 Cent’s “Magic Stick” remix. Both parties deny sexual intercourse, but do admit to having sexual contact involving a cigar, Monica’s mouth, and the oval office,
WORTH IT? Yes. Fellatio during work hours…where do we sign up?

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NAME: Bernie Madoff
MISTRESS: Sheryl Weinstein
COMPLEX SAYS: Exposed in a tell all memoir, Sheryl claims she was his side piece for about 20 years, often meeting in posh Manhattan hotels for “baths and vodka-fueled massages.” Oddly enough, it was reported that Sheryl would smoke marijuana before sex, just like Bernie’s wife Ruth would often do.
WORTH IT? No. Weinstein threw Madoff under the bus publicly, when she wrote he wasn’t “well-endowed.” Ouch.

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NAME: Jon Gosselin
MISTRESS: Deanna Hummel
COMPLEX SAYS: Pics surfaced of Jon looking on as the elementary school teacher tanned on his property. Then there were shots of her driving his whip. You dumbass, when you have 8 kids, awkward and embarrassing publicity is not good publicity.
WORTH IT? Well, yeah. A twenty-three year old school teacher versus a mother of eight? Just sayin’. Dude needed an excuse to rock all those Ed Hardy shirts.

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NAME: Hugh Grant
MISTRESS: Estella Marie-Thompson a.k.a. Divine Brown
COMPLEX SAYS: They went for a ride around the Boulevard. Divine’s mouth was full when they got caught for “lewd conduct.” He was charged with soliciting and Elizabeth Hurley left him.
WORTH IT? No. Hurley is a dime, and plus, he paid for a full session when he only received a trial version

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NAME: Kobe Bryant
MISTRESS: Katelyn Faber
COMPLEX SAYS: Can we blame Kobe for wanting to experience the full relaxation treatment with spa receptionist Katelyn? Though faced with charges of rape and time in prison, he insisted the affair was consensual. Years after proving his innocence, we learned about his alter-ego, Black Mamba, whom Katelyn already met back in Colorado.
WORTH IT? No. But luckily, after possible dropped sponsors and the negative limelight, Kobe’s hot wife still stands by his side.

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