D.C.'s Oldest Living Smut Kingpin Tells All Meet Dennis Sobin: Mayoral Candidate, Phone-Sex Innovator, Kennedy Center Playwright, Child-Porn Convict and Wannabe Family Man

About a decade ago, Darrin Sobin received a letter from an imprisoned man named Jailhouse Guitar Willie.

Willie had befriended Sobin’s father, Dennis Sobin, in prison. The elder Sobin, once dubbed Washington’s smut king, controlled swathes of the District’s sex industry in the 1980s. Since 1992, he’d been behind bars on charges related to fraud and sexual performance of a child. The conviction had cost Sobin his reputation as a pornographic Merry Prankster, not to mention what little remained of his phone-sex fortune.

But now, with his release date looming, he just wanted a happy reunion with his family.

Darrin Sobin had other ideas. Once employed in the family business, Darrin had earned his law degree and gone straight. After years of urging his pop to do the same, Darrin had given up. Now Guitar Willie was urging him to give the old letch one more chance.

“I hope you’ll go along with this, showing me you’re not as stubborn as your dad,” Willie wrote. He wasn’t the Sobin family’s only new jailhouse pen pal. Other letters came to Darrin’s kids. When one of them went unacknowledged, the jailed patriarch sent a nasty note. “If I do not get confirmation from [Darrin’s son] in his own writing by January, 15 2000 that he has received it, you and I will be locked in combat,” Dennis wrote, in a letter that became part of Darrin’s legal request for a restraining order against his father.

That’s because there are no Bureau of Prisons records for a Jailhouse Guitar Willie, or any other pseudonymous jailhouse letter-writers. They aren’t real. They lived entirely in the mind of Dennis Sobin, part of yet another scheme to remind people outside prison, even his own son, that he still existed. Today, seven years after his release, it’s a mission that still consumes him.

Dennis Sobin is setting me at ease about threesomes. “If someone’s feeling left out, you kind of draw ’em in,” Sobin says.

Despite his prodigious sexual career, Sobin remains cheerfully enthusiastic, even innocent, about the subject. There’s no leering or winking. Describing the intricacies of red-hot two-on-one action, his tone is about the same as a guy describing his friend’s marble counter tops.

Sobin is less of a down-market Hugh Hefner than a poor man’s Donald Trump, sharing the developer’s lust for self-promotion. Over the years, he funneled his smutty fortune into mayoral runs, guerilla campaigns against vice cops, and a series of low-budget local porno publications that were about the dirtiest things you could find in those pre-Internet days. Post-prison, he’s still self-promoting. He ran for mayor this summer, though he dropped out in July. In conversations, he still steers everything back to his prison art gallery, his guitar classes, and his political platform. And all I wanted to talk about was ’80s sleaze.

In fact, things are going reasonably well for Sobin. He lives in elder housing in Foggy Bottom on 23rd Street NW. The small apartment is better than the homeless shelter where he lived after his release, according to parole records. His girlfriend lives down the hall—close enough to make him coffee, but not so close as to limit his independence.

Behind Sobin is the trampoline he uses as a bed. Outside his window is the Kennedy Center, home to so much of his current scheming for rehabilitation: Sobin, it seems, has written a play, and it has somehow been accepted at the arts palace’s annual festival of new productions. It’s a musical. Naturally, it concerns a libertarian activist who overcomes his son’s machinations, becomes mayor, reconciles with his tormentors, and lives happily ever after.

Post-prison life has its humiliations, too. Sobin is registered with the District’s sex offender database; his mug shot and address are available online to any worried parent or old enemy. He says he only sees prostitutes as a customer now. In the lobby of his building, residents must sign in every 24 hours to prove they haven’t died. Sobin’s once thick, dark mustache has dispersed itself into a patchy salt-and-pepper beard. His busted nose now just makes him look beaten down.

But the worst humiliation of all remains Sobin’s unending war with his son. There was a restraining order against him before he even left prison. He can’t go to Darrin’s place of work, which may or may not have had something to do with his latest mayoral run. Because Darrin works in the office of D.C.’s attorney general—located in the Wilson Building—the old man would have been banned from his own office had he won, setting up the sort of legal battle Sobin relishes.