How a 'misery porn' star used Instagram to pimp San Francisco

The Point: Ricci Lee Wynne – dubbed a "lifelong criminal" by federal prosecutors – gained viral fame as a "video vigilante" who filmed himself tormenting homeless people and drug users in San Francisco. Media outlets, law enforcement and politicians portrayed the convicted felon as a heroic anti-crime crusader.

Wynne, on federal probation for a 2019 drug trafficking conviction, became a favorite of right-wing propaganda outlets like Fox. Bottom-feeding local TV stations also lapped up his amateur "misery porn" act, as did politicians like Mayor-elect Daniel Lurie.

But Wynne's journey from cocaine kingpin to anti-crime crusader came to a dramatic end last week. That's when San Francisco police arrested him on suspicion of pimping and pandering.

"Wynne’s arrest sprang from an investigation that named him as a suspect in the sexual assault of a 15-year-old," reported the San Francisco Standard. Authorities are also investigating "numerous reports" of Wynne "sexually assaulting and pimping minor girls," according to the San Francisco Chronicle.

District Attorney Brooke Jenkins – once among Wynne's fawning fans – has now charged him with human trafficking. Reports suggest more charges are pending.

Wynne's popular Instagram feed – where he regularly depicted himself as a luxuriating pimp fanning wads of cash in lavish settings – could help seal his doom. But it also raises a question: Why did so many people ignore the obvious red flags?

A 'misery porn' star rises

The Back Story: I first wrote about Ricci Wynne in a 2022 column headlined "Cocaine buffets and meth poop: Meet Twitter’s rising anti-San Francisco influencers." My column highlighted how social media algorithms had turned questionable characters like Wynne into viral mini-celebrities.

It detailed Wynne's recent criminal history:

In 2019, police arrested him in San Francisco after he advertised a “cocaine buffet” on Snapchat. They found a loaded gun, $6,000 in cash and more than 100 grams of cocaine in his apartment.

The Mercury News reported that Wynne was under investigation for “human and narcotics trafficking.” “The prosecution sentencing memo says ‘multiple females including an underage juvenile girl’ were also at the home,” wrote reporter Nate Gartrell. Wynne pleaded guilty to drug and weapons charges.

Federal prosecutors sought a 12-year sentence, but Wynne’s lawyers begged for mercy. They portrayed him as a child abuse victim with a learning disability who needed “sympathy,” not prison. Last December, U.S. District Judge Charles Breyer ordered Wynne released after nearly two years of “time served.”

Upon his 2021 release, Wynne resumed his social media antics, with a twist:

He traded Snapchat for Twitter, and he’s got a new drug hustle. Wynne patrols the Tenderloin and SoMa, using his camera to shame homeless drug users and exploit their squalor for online engagement.

Yet his self-promoting style of voyeurism, which preys mostly on the sick and vulnerable, is clearly a quest for social media clout rather than social compassion.

Wynne's tactics hit the algorithmic jackpot.

Obsessive anti-S.F. Twitter hits produced by people like Wynne ... feed right-wing media outlets hungry to portray The City as a dystopia rendered unlivable by Democratic policies. Their trolling supplies a steady stream of content focused on addiction, crime, homelessness ...

Wynne's videos were predatory. He bullied vulnerable people on city streets, often feigning concern and openly mocking them at the same time. I won't post his misery porn here, but it's easy enough to find if you're unfamiliar with his work.

'Bad for the World'

Wynne's videos went viral thanks to social media algorithms that favor "bad for the world" scenes of depravity. In turn, this virality attracted media outlets like Fox and the Daily Mail, which promoted Wynne because his criticism fed into their own biases.

Local TV stations got in on the action, since crime and controversy is a staple of nightly newscasts. All of this media attention, in turn, caused politicians to swarm like flies.

With the right-wing media ecosystem boosting his audience, Wynne sensed opportunity. He got political, bashing Democrats like Mayor London Breed, Gov. Gavin Newsom, Vice President Kamala Harris and former House Speaker Nancy Pelosi. And he became the city's chief scold against harm reduction and criminal justice reform, pushing draconian measures to address the city's ills. (Wynne supported the recall of former DA Chesa Boudin, whom he depicted as too soft on criminals.)

It was media catnip: A "reformed" drug trafficker exposing public squalor and shaming Democratic politicians. But there was a big problem with Wynne's anti-crime crusader narrative, and it was glaringly obvious on Instagram.

'Pimpin' on Instagram

As his notoriety grew, Wynne largely migrated from Twitter to Instagram, where his audience reached 105,000 followers. There, he revealed another side of his persona. In addition to videos of drug users and homeless people, he expanded his repertoire to include photos of himself living a grandiose lifestyle. Bedecked in designer clothes and frequenting high-end establishments, Wynne seemed to be doing conspicuously well for a federal probationer with no visible means of wealth.

He also posted selfies in local cannabis shops such as Stiizy despite the fact that the terms of his probation required him to abstain from drug use (marijuana remains illegal under federal law).

In rhyming photo captions, he spoke of cocaine deals, prostitution and evading federal wiretaps. "I'm a slick talkin' white boy like Gavin Newsom, from San Francisco to Sacramento pump'n prostitution," he wrote in 2022. "Dis a Gucci fit, no LVs [Louis Vuitton], I sold kilos bitch, not lbs," he wrote in a Gucci-clad selfie from a Gucci store.

This pompous glorification of crime did not befit a reformed criminal. I pointed out this glaring contradiction in 2022:

Some of @RawRicci415’s fans are upset that I criticize him, since he’s “in recovery.” But while he’s tormenting & vilifying drug users via his vigilante Twitter persona … he’s glorifying drug dealing, misogyny, pimping & violence over on Instagram.

Since then, Wynne's high-flying lifestyle has taken him far beyond San Francisco. He's posted photos of himself in Mexico and Japan, as well as New York, Hawaii, Lake Tahoe and Miami.

In Tokyo, he fanned a wad of hundred-dollar bills at Shibuya Station, sampled artisan cocktails at the trendy Bar Centifolia and rode the Shinkansen bullet train. In Mexico, he swam from the deck of a chartered boat and rode a horse along the beach. In Tahoe, he flaunted his Mercedes SUV and jewel-encrusted pinkie ring, introducing himself as "Vladimir McPimpin." "Gettin' money from a ho that's all I know," sang The Jacka and Berner in the background. In New York, he posed in front of the New York Stock Exchange and placed a wad of cash on the head of the "Fearless Girl Statue."

On November 23, he posted a video of himself in Miami, clad in bright orange Givenchy glasses while sitting in an orange Lamborghini with an orange duffel bag full of cash...and oranges.

Orange turned out to be his unlucky color. Police arrested him upon his return to San Francisco International Airport. He had nearly $80,000 in cash and a phone allegedly containing evidence of pimping, including "a cellphone in his name showing 18 months’ worth of ad postings for sex work, with logs of clients’ payments and dates," according to the SF Standard.

Days later, in court, he sported another orange ensemble: a jail uniform.

Ricci Wynne's predictable fall

Analysis: I knew this day would come. For one thing, I grew up with guys like Ricci Wynne. There are people who go straight and leave behind the criminal lifestyle, but they don't patrol the streets in search of conflict and attention. Wynne's haughty attitude and appetite for drama made him a ticking time bomb.

And then there was the Instagram account, where he avidly documented what appeared to be a lucrative crime-themed lifestyle. Federal probation officials will be hard-pressed to explain why they believed a convicted drug trafficker with few marketable skills could afford a swank high-rise apartment with Bay Bridge views, a $72,000 Mercedes, a Gucci and Givenchy wardrobe and regular (court-sanctioned) luxury travels around the globe.

Wynne's decision to broadcast the bling was dumb, but he couldn't help himself. While blasting addiction and crime for clicks, law enforcement officials allege that Wynne himself was addicted ... to an illicitly ostentatious lifestyle. And he was indisputably addicted to social media.

In fact, Wynne appears to have gotten hooked on multiple algorithms at once. One algorithm – the Predatory Voyeur algo – rewarded him for posting exploitative videos of the addicted and suffering. Another – the Right-Wing Influencer algo – boosted him for attacking Democrats. The third algorithm – the Luxury Lifestyle Influencer algo – may prove the most consequential of all. It lured Wynne into publicizing an opulent, pimp-coded lifestyle that will no doubt catch the interest of prosecutors.

Wynne gained online celebrity by using his camera to snitch on others. In the end, perhaps he couldn't help but snitch on himself. Like an Instagram Icarus, he flew too high. Now begins the predictable fall of this minor Greek myth in Gucci slippers.

How to Pimp a City

Pimps typically operate through a mix of force and seduction. Often, they lavish their victims with flattery and "love." They find a weakness and pretend to fill the void. In reality, however, a pimp only cares about himself. He lives to exploit and punish. He takes what he wants from others using coercion and/or force.

Wynne used force to – metaphorically – pimp the dysfunction and poverty of San Francisco's poorest residents. He shoved his camera in their faces, capitalizing on their misfortunes to glorify himself. He transformed suffering into profit, never hesitating to assume a threatening posture when someone tried to resist.

But the poor weren't the only people Wynne put into his service. His crusader act "turned out" many people in the San Francisco establishment who should have known better. Among the tricked:

Mayor-Elect Daniel Lurie

No one will ever accuse Daniel Lurie of having street smarts. One look at Wynne's Instagram feed should have been enough to make him persona non grata, but Lurie sought him out. The Levi-Strauss heir toured the Tenderloin with Wynne. He even filmed a video in which he thanked Wynne for his endorsement.

It's not clear why Lurie thought he needed Wynne's endorsement, but he should fire whichever staffer approved the stunt. If Lurie continues to be this gullible, his political career will be very short. What a terrible omen at a time when S.F. needs leaders with wisdom.

Lurie wasn't the only politician to get taken in by Wynne. Mayor London Breed posed with him (before he turned on her), and District 6 Supervisor Matt Dorsey joined Wynne at a rally to "save city streets from drugs."

California state Senator Brian W. Jones, R-San Diego, deserves a special mention for bringing Wynne all the way to Sacramento to testify at a committee hearing on homelessness.

The Federal Court system

Judge Charles Breyer gave Wynne a big break in 2019, ignoring pleas from federal prosecutors who sought a twelve-year sentence. That's understandable. Wynne's lawyers told a sob story about the childhood abuse he endured at the hands of his father, who was also a criminal.

But it's not clear why the court repeatedly approved Wynne's globe-trotting travels, or why no one in the federal probation system got suspicious after seeing his pimptastic 'Gram. In any case, I doubt Wynne can play the judge's heartstrings next time around.

San Francisco law enforcement

The San Francisco Deputy Sheriffs' Association proudly embraced Wynne and even considered endorsing him for public office. The union's president personally reached out to Wynne and constantly sought his attention on social media.

SF District Attorney Brooke Jenkins apparently invited Wynne into her office to hear his ideas for improving the city. Now she'll have to throw the book at him to save her own skin.

Was he openly clowning the cops for sport?

One exception: The SFPD, which has repeatedly tried to put Wynne where he belongs. Good job.

Bay Area TV stations:

KRON and ABC 7 competed to pump up Wynne's profile.

Lyanne Melendez of ABC 7 deserves special recognition for sucking up to the alleged pimp. In 2022, Melendez attacked me on Twitter, suggesting that I should be ashamed for criticizing such a nice young man. Ironically, she even had the nerve to call me "imberbe" (Spanish for "callow" or "inexperienced").

But this investigative journalism genius hasn't said a peep since Wynne's arrest. Imberbe, indeed.

Perhaps this tragic debacle will encourage local newsrooms to set a higher standard for those whom they choose to lionize. Doubtful. But if Wynne is found guilty, some local journalists should also face accountability for their complicity in building up his credibility, which may have been weaponized in the furtherance of the very criminality they spend so much time screeching about.

(Note to S.F. readers: There are a few other guilty so-called "journalists" not worth naming in print. You know who they are.)

The Abstinence-Only "Recovery" Movement

Wynne became the face of an aggressively anti-science movement opposed to evidence-based harm reduction strategies that are proven to save lives. This retrograde movement succeeded in closing down S.F.'s only overdose prevention center, which had successfully reversed over 300 overdoses.

S.F. has become a breeding ground for attention-seeking haters of harm reduction, and there are still a few wannabe Riccis on the scene – former drug dealers or unhinged types who harvest attention by punching down on the addicted or mentally ill. Wynne was their undisputed king, and his disgrace should spark some humility and soul-searching among those who embraced him.

Y Combinator CEO Garry Tan

Unsurprisingly, political novice Garry Tan jumped on the Ricci Wynne train. Wynne's bullying cruelty of the poor, coupled with his algorithmic savvy, apparently tickled Tan's fancy. In fact, Tan seemed to think Wynne's style of vigilante voyeurism was helping to make SF great again.

Tan claims to be religious and, since the Lord works in mysterious ways, I wonder what lesson he'll draw from this hot mess.

News reports suggest that Wynne's alleged prostitution ring catered to wealthy tech workers. That certainly complicates Tan's preferred narrative, which is that tech is here to clean up crime.

Ricci Wynne's future

Conclusion: You'll notice I didn't name Fox hosts like Jesse Watters or (former Fox host) Tucker Carlson as Wynne's marks. They were more like Wynne's clients. He gave them exactly what they wanted, and that's all that mattered.

After all, granting legitimacy to criminals is what they do every day at Fox. With Wynne likely unavailable for live interviews until sometime around mid-century, they'll forget all about him.

But don't count Ricci Wynne out for good. Over the last few months, he made yet another strategic move – by tapping into the MAGA algo. Just as he bet on Lurie to win the mayor's race, Wynne bet on Donald Trump to win the presidency.

It's clear that the SFPD and the DA want to put Ricci Wynne away for a long, long time. The way this country's going, however, don't be surprised if he winds up with a presidential pardon and a plum White House appointment. The Drug Enforcement Administration (DEA) seems like a good fit.