When Mistresses Attack!

Why did one of Jesse James’ mistresses just send a letter to Sandra Bullock? Rebecca Dana on the dangerous games Other Women play.

04.26.10 10:38 PM ET

“Dear Sandra,” the letter began, as if the author and recipient were ancient gal pals. “I’m sure your [sic] wondering why I’m writing…”

No, probably not—given that the author was Melissa Smith, Jesse James’ second tattooed mistress, and the recipient was Oscar-winner Sandra Bullock, his soon-to-be-ex-wife. Smith faxed a turgid apologia over to Bullock on Sunday, a mere three weeks after her relationship with James came to light. Apparently she couldn’t wait a moment longer, not even for grammar check.

Brooke Hundley’s note to the wife of ESPN analyst Steve Phillips references a “big birthmark on his crotch.”

In the note, Smith begs forgiveness “from the bottom of my heart” and invites Bullock to reach out, “on the phone or in person,” to chat further. It’s unclear how enticing a prospect this would be for the actress, who seems to be spending most of her time these days shopping for a divorce attorney. A copy of Smith’s note, including her loopy, elementary-school teacher signature at the bottom, leaked immediately to TMZ, almost as if it had been written with that result in mind.

The letter is a classic in the small but distinguished canon of writings sent from mistresses to wives, perhaps the most uncomfortable genre of correspondence ever. Entries in this category lack the clarity of purpose of notes exchanged between angry lovers: Dear John letters, breakup notes, Lindsay Lohan’s 2 a.m. e-rants at Samantha Ronson. When the Other Woman reaches out to the wife, her intentions are often much more complex, blending cruelty, guilt, pity—and, at least in the case of Smith, who’s been riding around Long Beach in a “Team Sandra” T-shirt, abject careerism.

“It’s beyond me why anyone would think it could be helpful in any way to write a letter to a woman whose life you have just blasted apart,” said Lisa Grunwald, co-editor, with her husband Stephen Adler, of two anthologies of American correspondence.

“It’s beyond me why anyone would think it could be helpful in any way to write a letter to a woman whose life you have just blasted apart,” said Lisa Grunwald, co-editor, with her husband, Stephen Adler, of two anthologies of American correspondence.

Grunwald said the mistress-to-wife letter is a rare and precious thing. She and Adler found not a one in the more than 400 missives they collected for Women’s Letters. Women are far likelier than men to write letters about relationships gone bad, she said, but even then, it’s highly unusual to address infidelity in such candid and personal terms. “It would be kind of like the driver of a car replaying an accident for you in slow motion and saying, ‘Let me show you exactly how and where I hit you. I really didn’t mean to, but look, you see how this fender crushed your kneecap? That was the point of maximum contact,’” Grunwald said.

For sheer turpitude, Smith’s letter to Bullock has nothing on young Brooke Hundley’s note to the wife of ESPN analyst Steve Phillips last year, in which she references a “big birthmark on his crotch,” and explained that Philips “enjoys being with me because I have more of a passion and drive to really do something with my life.” Smith also can’t compete with singer Alicia Keys, who last fall tweeted elliptically about her affair with producer Swizz Beatz, for all the world—including Beatz’ wife, Mashonda—to see.

Mashonda was quick to respond, via Twitlonger, which allows users to exceed the 140 character limit: “I feel that after [one] and a half years of you hiding this affair and acting like it [doesn't] exist, that now is the time to confront it, since you talk so openly about it now... You have no idea how much pain I was caused because of this affair.”

In trying to get the last word—or, at least, a word in edgewise—contemporary mistresses have typically been less direct, preferring open letters or comments to the media. This is how alleged Tiger Woods’ mistress Jaime Grubbs addressed the golfer’s wife, Elin, after news of that scandal broke in November. “I can’t describe how remorseful I am to have hurt her family,” Grubbs told Extra. Later in the interview, she expressed serious doubts, but no certainty, that she would go back to Woods, if given the opportunity. Back in 2008, Ashley Dupre apologized to Silda Spitzer during an interview with Diane Sawyer, saying that if she could say anything to the ex-governor’s wife it would be, “I’m sorry for your pain.”

Smith’s mea culpa is in the classic three-paragraph format. It has both a touch of humility (“I know that this message wills [sic] most likely go unanswered…”) and a good deal of contrition (“…will never forgive myself”). She doesn’t reference sex explicitly, distinguishing her from first mistress (and possible neo-Nazi) Michelle “Bombshell” McGee. Instead she refers to her “actions of engaging with a married man,” for which she has only “deepest regrets.”

It’s not what Alice Keppel would have written to Edward VII’s wife, Queen Alexandra, or what Rebecca West, Amber Reeves, or Margaret Sanger would have sent to Amy Catherine Robbins, wife of their lover H.G. Wells. But it’s also not Amy Fisher standing in Mary Jo Buttafuoco’s doorway with a gun.

Who knows, maybe Bullock will give her a call.

Correction: An earlier version reported the apology was faxed to Bullock’s production company; it was faxed to Bullock.

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Rebecca Dana is a senior correspondent for The Daily Beast. A former editor and reporter for The Wall Street Journal, she has also written for The New York Times, The New York Observer, Rolling Stone and Slate, among other publications.