Dennis Sobin first ran for D.C. mayor 40 years ago. Since then, he’s made millions in the sex trade, lost those millions, moved to Florida, spent years in prison, gotten out, launched a nonprofit, written plays for the Kennedy Center’s stage, and run a bevy of losing political campaigns.

But after all that, he’s back in pretty much the same spot four decades later. A lot has changed in D.C., but Sobin is still running for mayor.

He’s earned the Libertarian Party’s nomination to take on Mayor Muriel Bowser and he’s all set to appear on the ballot this November, elections officials confirm to Loose Lips. And Sobin tells LL that he’ll run on much the same platform that has defined his wild career in D.C. politics: The full legalization of drugs and sex work.

Sobin was the master of over-the-top theatrics in his heyday, running a series of campaigns in the 1980s staffed by sex workers and funded by his massage parlors, but don’t expect any of that this time around. He says he’s “a little more mellow now,” and why shouldn’t he be? City Paper declared Sobin “D.C.’s oldest living smut kingpin” in its last cover story on him, and that was 12 years ago—he’ll turn 79 in a few months.

He’d have a snowball’s chance in hell of winning as a Libertarian in D.C. even without his particular policy positions or his sordid past (there are something like 2,300 registered Libertarians in the city, as of June 30). So why keep running? He hasn’t been much involved in local politics since his last mayoral bid in 2010 and he has his advocacy work with incarcerated artists to occupy him.

Yet Sobin sees this as his “last hurrah” to make something interesting out of his self-described “twilight years.” After all, he notes that he’s actually a few months younger than President Joe Biden, so he sees no reason not to make another go of it.

“I think Bowser really has done a good job, and I would follow her policies in every area except for law enforcement,” Sobin says. “I want to concentrate on real crime, not have them bother with the enforcement of victimless things like sex and drugs. If, during the campaign, I could convince the mayor that’s the way to go, I think we would be on the right track … and who knows, if I become mayor, I could hire her as my assistant.”

If anything, Sobin believes mainstream politics have moved pretty firmly in his direction over the last few years. Not only has D.C. decriminalized marijuana and some psychedelics, but there have been at least some conversations about decriminalizing sex work too—he notes that “even the mayor uses” the term “sex worker” instead of the more loaded term “prostitute.”

He notes that he doesn’t believe quite as fervently in the value of “private ownership” as many of his fellow Libertarians, and he sees the value in the welfare state (he relies on Social Security checks and food stamps to get by, so Sobin’s an unusual fit for such a virulently anti-government party). That’s why he expects his once-radical message might catch on a bit more than it did in his previous runs for mayor and Council.

“I happen to be addicted to a drug myself, and that’s Viagra,” Sobin says. “If they made it illegal, I might go out and steal and shoplift, too, if I couldn’t afford it. So what’s the harm of giving someone heroin if they’re addicted the way I’m addicted to Viagra?”

Of course, Sobin is well aware that people will be skeptical of him because of his past—his time running brothels and producing porno magazines is one thing, but his convictions on fraud and child pornography charges are another.

He insists he’s become more “educated and insightful over the years,” and has changed many of his ways. “I’m no longer a provider of sexual services, but I am still a consumer,” he notes, but says he has otherwise stayed out of trouble. Court records confirm that Sobin has certainly slowed down a bit compared to his younger days—his last case in D.C. Superior Court involved him suing the Department of Motor Vehicles in 2021, alleging fraud. It went about the way you might expect and was dismissed in May.

Yet he isn’t much concerned with what people might think of him, buying into P.T. Barnum’s old maxim that “there’s no such thing as bad publicity.”

“People don’t remember a lot of stuff when they walk into a polling place, but they may well look at the ballot and say ‘Hey, I remember his name,’” Sobin says.

LL might suggest, however, that most people have a negative association with Sobin’s name, if they remember it at all. He’s periodically made headlines over the past few years with his very public, very ugly disputes with an estranged son—the younger Sobin once had a restraining order against his father and worked for the District government, meaning that Sobin wouldn’t be allowed to go to the Wilson Building if he’d somehow won his mayoral bid.

That son has since left for a different job, per his LinkedIn page, so Sobin is in the clear on that count. However, their relationship remains frosty—Sobin says the two haven’t spoken in years.

In the likely scenario that Sobin loses, he says he’ll have plenty to keep himself busy. He’ll keep on running his Prisons Foundation and Safe Streets Arts Foundation, nonprofits that work with incarcerated people and help distribute their books and other works of art.

He seems generally content with the idea that he’s pretty much faded into obscurity these days, quite the statement for a man that was once a fixture on City Paper’s pages (he infamously appeared on one cover in 1988 while completely nude and holding a blow-up sex doll). This may well be his last appearance in this publication or any other.

And that’s fine by him. Sobin says he’s never actually read any of City Paper’s voluminous coverage of his life’s twists and turns.

“The way I see it, it’d either make me feel bad, or it’d inflate my ego,” Sobin says. “Neither seems good.”