Credit: Photos by Darrow Montgomery

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.

(Photograph by Darrow Montgomery)

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.

(Photograph by Darrow Montgomery)

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.

One August night in 1988, Bernard Emert, a plainclothes officer with the Metropolitan Police Department, pulled up to 1518 K St NW. A suite in the building housed the Washington Center for Better Living, which purported to be a prostitution-research facility.

Actual researchers would have found a lot of material at the center. Tenants in the building periodically found used condoms in stairwells. An earlier police tour of the facility had found nearly nothing in the office besides mattresses and trash cans that brimmed with condoms and wadded-up paper towels.

A woman named Holly Thompson approached Emert and asked if he was “dating.” They agreed on $50 for two sex acts—court documents don’t specify which—and she led him upstairs. Sitting at a desk in front was Dennis Sobin, who demanded another $10 for use of one of the center’s rooms.

Thompson led Emert into a room and began undressing. When Emert said he was a cop, Thompson cried out, “Dennis, Dennis, Dennis, this man says he’s the police!” Sobin and Thompson were arrested. Sobin received a $500 fine and 180 days in jail for operating a disorderly house.

This was the harshest sentence Sobin received in his first eight years as Washington’s most prolific—and most public—sex entrepreneur. It’s surprising that he hadn’t gotten busted more often. The Washington Center for Better Living embodied the Sobin ethos—why be discreet when you can be outrageous?

Sobin says he never intended to become what one Washington Post writer dubbed “the J.P. Morgan of the grope set.” He began the 1970s in New York, a married sociologist with two young sons. He’d only had sex with his wife Paulette, who he’d been dating since he was 15. Sobin says he didn’t even know women could have orgasms.

(Photograph by Darrow Montgomery)

When his marriage began to disintegrate, however, Sobin entered New York’s swingers’ scene. Alas, even 1970s New York didn’t offer the freedom he craved: police arrested Sobin in 1972 for dancing with nude women at a club. Opposing government-enforced prudery became his guiding philosophy. Sobin says he moved to Washington right before the 1976 Bicentennial to be a libertarian activist.

In D.C., Sobin began publishing Free Spirit, the first of many publications he used to advance his politics: gay rights, legalized drugs and prostitution. Among other things, he ran sketches of vice cops who appeared to testify in court so cruising gay men and prostitutes could avoid them. But mainly, Sobin’s publications advanced Dennis Sobin, making him a local celebrity, of sorts.

Sobin put his words about sexual liberation into action in 1979 when he began running a sex club out of his home on N Street SE near where Nationals Park stands today. According to the testimony of undercover officers who infiltrated the establishment, visitors to the Playground Swing Club were met by Sobin or one of his associates at the front door. Admission required $15 per couple and a first name signature on a contract, which was then torn up and thrown away. Outfitted in robes provided by the club, they could then dance, watch porn on a LaserDisc player, or have sex in the “Fantasy Room.”

Police raiding the club came away with several couples on charges of oral sodomy. Sobin told reporters that the cops also briefly took possession of his own “double king size” mattress.

Beyond his club, Sobin began taking over escort services and massage parlors whose owners had been indicted or evicted. You’d think the repeated police investigations would have made Sobin want to obscure details about the money they made. But Sobin blabbed away in The Washington Post, estimating that two neighboring massage parlors made $500,000 a year. In 1987, he boasted to the newspaper that his sex business grossed $3 million dollars yearly, most of that profit.

Sometimes, Sobin earned that money with his own body. He once had sex with another activist prostitute at a bachelor party for $300. He also began producing and acting in porn movies. In one, The Last Condom, Sobin plays a hapless convention-goer who picks up a prostitute. As she waits in his hotel room, he fiddles in the bathroom with protection. Unfortunately for Sobin’s character, the rubbers can talk. “Will you look at this guy?” sneers one condom.

While Sobin diversified his sex business, the rest of family got in on the action, too. Paulette, who had been living in Hawaii with her two sons, Darrin and Teague, moved to Washington, Sobin says, after Sobin made it a condition for his sending child support money. At his urging, according to Sobin, she started her own escort business. Paulette’s success inspired Sobin to work even harder.

“Even her operation could be improved upon,” Sobin says.

Dennis Sobin is on the mayoral campaign trail, and things aren’t going well. The audience members at the D.C. Democratic State Convention are rewarding his pro-convict, anti-drug platform with laughter and applause, but that’s about all they’re giving him.

Sobin’s entourage usually consists only of girlfriend Argentilhia Boechat, a small, elderly Brazilian woman fond of wearing dark sunglasses and abstract patterns. His campaign manager is Richard Dyches, a convicted murderer currently imprisoned in Nevada. It’s not clear whether anyone in the room actually knows who he is, or at least who he used to be. Well before primary day, he’ll be out of the race.

Sobin’s first four runs for city office happened when he was actually well-known as a menace. He used to have a mob of prostitutes working his campaigns, which were sometimes funded directly by his massage parlors. Customers at the Adam and Eve and Paradise parlors “donated” $35 to two political action committees associated with the business for a half-hour of service. Because only donors of $50 or more were disclosed in PAC filings, the johns weren’t immortalized in campaign finance reports.

As treasurer and organizer of both PACs, Sobin felt free to open his political war chest to a variety of causes. He printed condoms promoting his campaigns; he distributed clean syringes to drug addicts. Prostitution money also fed Sobin’s print-media ambitions, an on-and-off stable of publications that included the Washington Pist, the Baltimore Freedom Times, and the Sophisticate Video Review. He also started Crime Solvers magazine, filled with tales of the true crimes Sobin thought police should pursue instead of raiding the Playground Swing Club.

For a time, Sobin and his cohorts came across as more Weather Underground than the Libertarian Party. Sobin worked, both politically and in his businesses, with members of a group called C.O.Y.O.T.E., a prostitutes union that held some of its meetings in abandoned buildings. Prissy Williams-Godfrey, a C.O.Y.O.T.E. organizer, detailed at Sobin’s fraud trial how the prostitutes would convince their johns to let them use their credit cards to fund political activity. Williams-Godfrey considered Sobin the man who would take her from a self-described whore to a political boss: “I searched for many years in every major city and every little cubbyhole town until I found Dennis Sobin,” she said.

And Sobin was a hard boss to stop. After the Adam and Eve and Paradise massage parlors were closed by the property owner, Sobin crowed to media that he and his employees would set up in the Godfather, a strip club he had recently bought: “There will be men and women dancing nude today, tonight and tomorrow.”

Outside the Godfather, Sobin hung a sign that said “Under Nude Management,” letting the neighborhood know Sobin had moved in.

It’s no surprise that the sex-entrepreneurial self-promotion overlapped with the political-organizing self-promotion. Sobin’s runs for office, like his other attention-seeking schemes, centered on his campaign to legalize more sex acts—which, completing the circle, would make it easier to run his business. Nearly all of the fortune Sobin amassed seems to have funded his political activities. At his bankruptcy trial, even prosecution witnesses said Sobin bought his clothes from thrift stores. Former common-law wife Eleanor Pohorylo said she had to fight Sobin to get money for basic household goods.

According to Pohorylo, his only affectations to the high life were a 1914 Model T and replica Model A. “He always thought that everything should go into the business or his what he called ‘political war chest,’” she testified.

An attractive black couple is on a date. She’s in a red top with puffy shoulders, he’s wearing a bright blue shirt under a canary yellow jacket.

“Every time I dial 9-SOCIAL party line at 976-2425 I’m connected to lots of different women from the metro area’s wild adult 24-hour party line and we get to talk and exchange telephone numbers,” he says.

“Plenty of men call too. I get automatically connected to everyone who’s called 9-SOCIAL for a party line conference call,” she says.

Although he never appears in it, that commercial would help make Sobin wealthy—even wealthy enough to risk prison.

There isn’t much room for innovation in the oldest profession, a fact that must have irritated someone as unconventional as Sobin. But in 1985, he heard from a man named Brad Woodward, who operated what is thought to be the first pay-by-the minute telephone line in the area—at the time, a daily soap opera daily in one-minute installments.

First used to poll television viewers, “976” lines multiplied after telephone deregulation. Operators and the local phone company would split the profits. As an indication of how little anyone understood the market at its beginning, Woodward and Sobin’s first 976 line offered recordings of children’s stories. They soon dropped it for lack of interest.

The lines wouldn’t succeed until Sobin added what he did best: sex. According to Woodward’s later court testimony, the two men realized the potential for a sex line whose owner who could advertise in his own papers.

Sobin had access to another resource: women who could staff the sex lines. Chief among them was Pohorylo, according to court transcripts, a convicted prostitute and recovering Dilaudid addict Sobin had been living with on-and-off since 1980. Soon, along with other employees Sobin had met via his papers and escort businesses, Pohorylo was making adult recordings and changing tapes for Sobin’s lines. Pohorylo told the Post that some days, the lines were so popular that she had to call the sex line office from a pay phone to make new recordings.

Sobin and Woodward consolidated their lines into the Bruce Corporation, named after Lenny Bruce. They also launched 9-SOCIAL. As the commercial suggests, its appeal lay in the possibility that you’d meet someone on the line, exchange numbers, and let things progress from there. While the recorded sex lines were popular, they only made between $5,000 and $10,000 a month. 9-SOCIAL made far more, peaking at $140,000 a month.

If the rise and fall of Dennis Sobin were a movie, this is when the montage starts. Sobin and Woodward had built what was, for a time, the perfect business. Money rolled in. Sobin needed only to hire his women to make sexy telephone recordings—and police the lines against troublemakers attempting drug deals.

Sobin eventually set up lines elsewhere on the East Coast. “[Bruce] seemed to actually be leading the industry,” Jon Kemp, one of Sobin’s employees, recalled at the fraud trial.

Perhaps even better than the money was the publicity his newfound wealth generated. Sobin appeared on daytime talk shows, including The Sally Jesse Raphael Show and Geraldo. In episodes with names like “I Took My Son to a Prostitute” and “Men Who Marry Prostitutes,” Sobin relished playing the villain, sitting dutifully for scolding from audience members.

As Sobin’s common-law wife, Pohorylo fashioned as much of a home life for Sobin and her three children as his wandering sexual appetite would allow.

But inevitably, the good times curdled. A series of other business ventures had soured, and Sobin was entangled in several lawsuits, including a wrongful death case filed by the widow of a firefighter who died fighting a blaze at a Sobin massage parlor. Then a legal dispute with C&P Telephone delayed payments. Lawmakers in Maryland and D.C. passed new legal restrictions that cut into business. Customers drifted for other reasons, too. “This type of programming would hit very big and was very popular, but people quickly got bored with it or they had huge phone bills they couldn’t pay,” Woodward testified at the fraud trial.

Early in 1987, Sobin decided to file for bankruptcy, first concealing his phone-sex money from creditors until he could reach it later, according to a later appeals-court opinion.

Sobin proved to be mostly incompetent at fraud. Attempting to hide revenues in dummy bank accounts in Virginia and Long Island, Sobin used aliases like Mary Ann Evans, the name of pseudonymous author George Eliot, and Dennis Kasobin. Besides their similar first and last names, Kasobin and Sobin also shared the same middle name and birthday.

Right before he filed for bankruptcy, Sobin passed control of Bruce to some of his employees while he continued to direct the company from the background. He directed them to sell the company to a lawyer, with a front company also owned by Sobin pocketing a 90 percent “management fee” from the sale. As monies held by C&P were released to Bruce, Sobin continued to siphon them away into bank and brokerage accounts.

In 1992, Sobin was found guilty of six counts relating to bankruptcy fraud. But by then, he had bigger legal troubles.

Child porn hangs over any discussion of Sobin. There’s a brothel owner and porn producer, he was in prison, and now he’s running for mayor—isn’t that funny? There’s an ex-con, and now he’s running a non-profit for prisoners—isn’t that nice? But, the question inevitably comes, what was he in prison for? And the answer isn’t charming on any level.

In 1991, with revenue from his phone-sex lines evaporating, and his bankruptcy fraud under investigation, Sobin traveled to Florida’s Pasco County with Pohorylo’s 6-year-old daughter and 8-year-old son. In the family, the kids were treated like Sobin’s biological children. He later admitted in a custody hearing that they weren’t.

Sobin came to Florida, he said, to make a documentary about nudism in America. In part of the documentary, he planned to have chaste shots of the children naked at a nudist resort. The nudists who saw Sobin filming, however, didn’t think the shots were so chaste. They called the police, who searched Sobin’s van and found porn videos. He was charged with racketeering and sexual performance of a child.

Sobin rejected a plea offer that would have saved him any time in prison. Typically, he took the case as a challenge. Before long, a publication called Inside Pasco County appeared, featuring an article that labeled the local sheriff “Pasco County’s Number 1 Swinger.” Sobin denied involvement, but it bore his style, especially the inclusion of hard-core porn in the magazine.

While he went through the legal system, the antics that had been tolerated in Washington seemed to go horribly awry in the Sunshine State. When Eleanor Pohorylo moved to Florida, she was indicted on racketeering charges. Later, when police pulled her over with a “gentleman friend,” they discovered marijuana in her purse.

Sobin didn’t have any luck, either. His attempts to repeal Pasco County’s adult laws through referenda were thrown out. Meanwhile, his peculiar style of porn production baffled Floridians. A Washington City Paper article at the time captured Sobin’s questioning of a Tampa strip club owner in a video called Skin Games. The interview featured probes like “If you had a picture of [U.S. Supreme Court Associate] Justice [Antonin] Scalia jerking off, what would you do with it?”

At the pornography trial, a witness testified that Sobin had filmed Pohorylo’s daughter holding a banana near her vagina. Sobin’s defense attorney suggested that he was a naïve dreamer, while the prosecutor said Sobin was planning to market the videos to the child porn underground. Sobin was convicted and sentenced to 12 years in prison.

The conviction marked the end of Sobin’s makeshift family. Pohorylo, who had testified against Sobin as part of a deal with prosecutors, soon remarried and disappeared. The children Sobin had raised as his own entered Virginia’s foster care system. As for his biological kids, they were grown and far away.

In his self-published memoir, From Prison to Kennedy Center Stage, Sobin compares his child-porn trial to the Salem Witch Trials. In a stranger portion of the book, Sobin recounts the story of Ben, a man he met in prison whose crime was “pushing the save key on his computer.” Although it’s not clear what Ben saved that brought him so much trouble, it seems to be child porn.

Sobin writes: “I suspect they involved pictures of over-aged or under-aged individuals in less than full clothing. Ben had been curious, so he looked at them. Can’t a person in a free society do that?”

The law, and most people’s sense of basic ethics, says no. But even behind bars, Sobin kept trying to debate the subject, reaching out to the only people he had left.

“My family lives a bunker lifestyle,” Darrin Sobin testified. “We feel like we are being stalked continuously and relentlessly.” Sobin went on to explain how, because of the stalking, he won’t let his sons use social networking sites and how the family sometimes walks separately so the stalkers won’t learn his sons’ faces.

His alleged stalker, Dennis Sobin, sat across the courtroom. Even though this hearing in June 2010 was meant to determine whether Darrin’s restraining order against his father should be extended another year, Sobin is effectively on trial again. The charge: being an atrocious, and possibly dangerous, father.

While Dennis Sobin abandoned his ordinary middle class life as spectacularly as he could, Darrin Sobin struggled from his teens to become like anyone whose father wasn’t the porn king.

While Sobin’s parents, as owners of rival escort services, clashed in business, they also feuded over custody. One Christmas Day, Sobin organized a mob of prostitutes to picket the home Darrin shared with his mother and brother. The prostitutes carried signs demanding that Sobin receive his “father’s rights.”

By the time Darrin was 16, he was answering telephones at one of the escort services, having only the vaguest idea that the business was illegal. At 19, in 1985, Darrin moved to his uncle’s California ranch for the summer as a way of leaving the family business behind in between semesters at George Washington University.

His mother moved to California too, intending to use the ranch to grow marijuana, according to D.C. Court of Appeals documents over whether Darrin should eventually be admitted to the bar. Although he attempted to avoid the illegal work on the ranch, his uncle eventually convinced him that the farm needed his help to stay solvent. Sobin began laying pipes and digging ditches to irrigate the plants. Right as he was about to leave to return to college, police on their way to raid the farm arrested him.

Soon he was facing federal charges relating to both the escort business and the farm. After pleading guilty, he received five years probation, according to the bar-admission documents.

Dennis Sobin opened a surfing and skating equipment shop in Alexandria for Darrin to run, but Darrin moved away from his family business. After attending law school and interning with the federal judge who originally sentenced him, Darrin Sobin might have thought he had finally built a life separate from his father’s influence. But for the younger Sobin, who declined to comment for this article, his problems with his father were just beginning.

While his father was imprisoned, first in Florida and then in federal prison in Virginia, Darrin Sobin attempted what amounted to a homemade Dale Carnegie correspondence course to make his father more bearable. In one letter, he proposed 11 things Sobin could start doing so he could have a relationship with Darrin after his release, like No. 4, “Stop trying to shock people (this includes not cursing)” and No. 9, “Try never to use the word ‘hypocrisy’ again.”

Judging by Darrin’s later letters, Dennis Sobin refused. Instead, he sent his son a short story titled “A Son’s Commitment.” In the story, a father released from prison plots to plant drugs at his son Aaron’s apartment and, by getting him incarcerated, saves his son’s marriage to a woman whose name rhymes with the real name of Darrin’s wife.

Before Sobin came out of federal prison in January 2003, Darrin already had a restraining order against him. Sobin went on to violate it by attempting to attend hearings on crime issues at the Wilson Building—the site of Darrin’s office. On his way to the hearing, Sobin was arrested for violating the restraining order.

The mystery behind Sobin’s continued harassment of his son is why he even cares. Sobin has always presented himself as a man more interested in his hedonism than raising a family—Pohorylo estimated that when she was living with him, Sobin lived with other women a third of the time.

But there’s something that draws Sobin to his son, no matter how many lawyers and judges tell him to stay away. In a letter he sent to Darrin during one of their many court battles, Sobin wrote about seeing his son at trial, “Forgive me for saying it but this is a hell of a way for us to be communicating. But it’s better than nothing! Definitely better!” It’s a pretty good bet the chance for proximity to his son—or at least the chance to do legal battle over said proximity, or at least the chance to hear people talk about the unlikely prospect of said legal battle over said proximity—motivated his latest mayoral run.

In 2010, the restraining order came before Judge José M. López for renewal. Dennis Sobin’s lawyer submitted a sheaf of documents arguing, essentially, that Sobin is just too nice to be a stalker. They included a grant from George Soros’s Open Society Institute for Sobin’s Prisons Foundation. “If the below email and attachments don’t impress Judge López, nothing will,” Sobin wrote to his lawyer.

López, in fact, wasn’t impressed. Last month, he extended the restraining order for another year. “The Dennis Sobin that gives free guitar lessons to the elderly, is not the same person when it comes to Darren Sobin,” he wrote in the order.

The crowd seated inside the Kennedy Center’s Terrace Theater is waiting to see the musical Sobin wrote about his arrest, Busted at City Hall. Or, as it could be called, The Dennis Sobin Story, If Dennis Sobin Won.

The musical is part of Sobin’s foundation’s contribution to the Kennedy Center’s Page to Stage festival. Sobin’s foundation has produced prisoners’ plays at the Kennedy Center in the past, and now it’s Sobin’s turn. The Kennedy Center holds a special power over Sobin. He mentioned his guitar performances there repeatedly during campaign appearances. His memoir is called From Prison to Kennedy Center Stage.

After a performance by a police band, three young women take the stage. Sobin sits behind a piano player. For once in his life, he’s mostly out of view.

The invisible man is a guy who got rich off of Washington’s appetite for sex. He made, concealed, and lost a fortune along the way. He racked up convictions and sexual partners. He did terrible things. He never apologized. And he made life hell for members of the family he dragged along with him. And he also built himself up again after his conviction, after a fashion. Should that recovery, the transformation into a nice old man who teaches guitar and champions jailhouse artists and only really acts like a menace to one person, outweigh everything else? The musical is Sobin’s argument for yes.

Onstage, with a woman playing the hero’s role, the drama traipses through Sobin’s old prison term and his new run for mayor. But there’s a twist: Sobin actually gets elected. At the end, Mayor Sobin has a friendly chat in city hall with a senator and the guard who arrested him.

But the musical’s true climax comes while the Sobin character is arrested at city hall—by authorities who’ve been alerted by his own son. As the guard sing-drones about his Miranda rights, Sobin asks the eternal porn king questions: “How can this happen to someone so kind? Someone who only has love on his mind?”