The rise and fall and rise of Patrick Painter

In the wake of a torrential downpour in early January, a sizeable and slightly random group of artists, collectors and art-curious celebrities descended upon the L.A. Convention Center for an “opening night premiere party”—hosted by Mad Men star Jon Hamm—celebrating the 23rd edition of the L.A. Art Show. Inside this somewhat inscrutable international sprawl, stateside dealers seemed split between kitschy street-art samplings and secondary-market standbys, while Asian and European powerhouses like Seoul’s SM Fine Art and Berlin’s König Galerie respectively showcased Korean Dansaekhwa masters and the in-demand minimalist sculptures of Mexican conceptual artist Jose Dávila. Elsewhere a silver-maned Matthew Modine entertained a gaggle of collectors admiring the actor’s photography from the set of Stanley Kubrick’s Full Metal Jacket, while another group of Hollywood heavies in one of the fair’s larger booths circled around a husky wheelchair-bound dealer. He was wearing snakeskin tennis shoes, black Adidas track pants, a billowy black T-shirt, black knit gloves, blue-lensed Persols, and a tiny black beanie with a sequined Chanel logo that belonged to his wife.

Though he’d shed his second skin of cashmere tracksuits, custom Alexander McQueen furs and blinged-out Chrome Hearts baubles; and his hair had mellowed from its trademark platinum shock to a buzzed pewter; and his once-intimidating bulldog posture had atrophied around the chrome frame of his Nova wheelchair; and he was sober, headed home early—not famously passed out inside his booth in the salad days of Art Basel—there was no mistaking the man in black tonight. This was Patrick Painter, perhaps the most complicated and controversial, iconic yet problematic, Angeleno art dealer to reach the high climes of the international art world...and then all but vanish.

A recent post to the gallery’s Instagram said: “In case you’re wondering... We are still located @ Bergamot Station in Santa Monica!” Such a pitiful social-media plea would have been unthinkable in Painter’s prime, when he lorded over the L.A. scene like the bastard son of P. T. Barnum and Suge Knight, a street-styled autodidact art savant who was mentored by a Who’s Who of legendary dealers, including Leo Castelli and Walter Hopps, by day and by night scandalized cities from L.A. to Berlin alongside art gods like Mike Kelley and Martin Kippenberger.

From the beginning the Long Beach-born dealer identified his operation—Patrick Painter, Inc.—as a corporation first and a gallery second, a nod to another early mentor, pioneering New York dealer Marian Goodman. “She’d say, ‘It’s the art business, Patrick, not a hobby. Always remember that,’” recalls Painter. “I always wanted to keep that in mind.”

Fueled by four-days-on, one-day-off cocaine benders, Painter did just that, once presiding over four L.A. galleries—two in Bergamot Station, one in the Pacific Design Center and another on Melrose—with assistance from a string of top-flight directors (Sarah Watson, Sachi Yoshimoto, Mayo Thompson, Heather Harmon, Michael Briggs) who oversaw a global footprint that spanned the early “hotel fairs” to Art Basel.

“Patrick Painter, to me, is a myth,” says ascendant L.A. gallerist Nino Mier. “I wasn’t a collector, advisor or gallerist when he was at his peak, but I look back at what he did, who he showed and how he conducted his business—good and bad—and I have to say that he had massive balls. He showed the hard stuff and worked with not only some of my favorite artists but he also offered a contrarian vision to the L.A. art scene.”

“In New York everybody had a couple of great artists in the stable, but Patrick had a pretty concentrated group in one place—it was just this powerhouse,” says Sarah Watson, now the director of Sprueth Magers Los Angeles, who left her director position at Deitch Projects in 1997 to open Painter’s gallery. “People knew him really well through his editions, and artists loved to work with him. He was maybe controversial at that time—here’s this new guy taking all these artists and doing well—but that’s the art world.”

Early on Painter made it a principle to never consign work from Manhattan galleries—“People were writing checks to New York for artists who lived down the street,” he says. “I never understood that”—and his mafia-like presence, embellished with a gangster rapper’s wardrobe and a fleet of Lamborghinis (including a Versace edition), lent a certain wild-west cachet to a wide swath of artists who are now at the center of today’s contemporary discourse.

“Once I was at a party in London’s Cadogan Square hosted by Ivor Braka, a prestigious British art dealer,” recalls Marc Spiegler, the global director of Art Basel. “I was talking to a young British dealer, and we were looking at a Francis Picabia painting. Patrick rolls up to the two of us in his velour tracksuit and rocking a dookie rope chain. He says, ‘Yo, I’ve got the greatest effing Picabia in L.A.’ He showed us a picture on his phone and then strode away into the night. And this tony old Etonian dealer says, ‘Who was that?’ I said, ‘That’s Patrick Painter.’ And he says, gobsmacked, ‘Impossible! Patrick Painter is a legendary Los Angeles gallerist.’ And I said, ‘No, man, believe me, that’s Patrick Painter. ’”

Despite appearances, Painter’s eye was indeed the stuff of legend. He was the first person to show Picabia in L.A. His pioneering multiples company, Patrick Painter Editions, put out high-caliber works with nearly every contemporary luminary (and repped the estate of conceptual icon Bas Jan Ader) during its 17-year run. His brick-and-mortar operations would give a major L.A. platform to countless others: Glenn Brown, Richard Prince, Harmony Korine, Albert Oehlen, Shirin Neshat, Sigmar Polke, André Butzer, George Condo, Larry Johnson, Sylvie Fleury, Liz Craft, Peter Saul, Kenny Scharf, Won Ju Lim, Valie Export, Jim Shaw, Mike Kelley and Paul McCarthy. The latter three, who have since become the holy trinity of the contemporary L.A. scene, decamped from Rosamund Felsen Gallery to form the hometown core of his roster for nearly a decade.

“He offered them money to make that change, and they were getting to that point where they wanted to do works that required fabrication and I didn’t have that kind of money, so he gave it to them,” says Felsen, who first met Painter at her gallery, then based in West Hollywood, during a show for Kelley. “You couldn’t have a relationship with him, at least I couldn’t. He wasn’t normal. We would communicate because he was buying art from me, but then it became clear that he wanted what I had, and he took it with money, so that was the end. He was not a friend. He was a junkie who had major health and psychological problems, that was my opinion of him.”

“Everyone likes to blame dealers for things that artists do, but the artists made the choices to go elsewhere,” says Watson. “Although I do sympathize with the dealers when they leave, there are ways of handling it elegantly.”

When he opened his gallery in 1997, Painter took over the space of another pioneering L.A. dealer, Burnett Miller, just two doors down from Felsen. He also began selling the works of his new stars for much higher prices—still relatively cheap in today’s market—and helped facilitate the production of marquee pieces like Poetics, Kelley’s large-scale video-projection with Tony Oursler, and John Glenn Memorial Detroit River Reclamation Project, a gallery-filling sculptural installation that debuted in Kelley’s “Black Out” show at Painter’s Bergamot space in 2002. A precursor of sorts to the artist’s Memory Ware and Kandor series, the piece was fabricated from the color-coded flotsam and jetsam Kelley dredged from the eponymous waterway. While Felsen surely felt burned, her former artists were now making the most epic work (and money) of their careers.

“He entered the scene in Los Angeles at this interesting time,” says Jeffrey Deitch. “There was a wipeout after the early-nineties art depression and several galleries closed up shop, and he came in during this period when it was wide open and quickly established himself as the most interesting L.A. gallery for the newer generation of artists.”

The New York-based gallerist and former MOCA director was one of the first art-world players to meet Painter back in the late 1980s, when he was “a hunky guy in a tweed jacket” who collected big-ticket works—Sigmar Polke, On Kawara and Ed Ruscha paintings; Robert Gober, Donald Judd and Bruce Nauman sculptures—by the bunches from the world’s top galleries and auction houses with the backing of his then-girlfriend Winnie Fung, whose father founded the Hong Kong financial services giant Sun Hung Kai & Co. The couple even commissioned Julian Schnabel to make plate paintings of themselves. In the wake of their 1989 breakup, however, Painter and Fung attempted to offload a portrait of Schnabel’s old flame Ahn Duong for an estimate three times higher than what they had purchased it for just four years prior. When it failed to sell at a 1990 Sotheby’s auction, the couple—and by default, Schnabel—were skewered in multiple articles, as well as in Anthony Haden-Guest’s 1996 art-world tell-all True Colors, as arbiters of the eighties bubble.

“He was one of the big buyers, and then he started this multiples business in Hong Kong,” says Deitch. Painter launched his editions company in 1990 with $100,000 in start-up capital from his mother, Lila Lee Escalante, who married Conrad Escalante, founder of the Superior Outdoor Display sign company, and became one of richest women in Long Beach. With some help from a printer in Vancouver who worked with Stan Douglas, Rodney Graham and Jeff Wall, he launched the business with photo editions by Wall, Juan Muñoz, Richard Prince and Larry Johnson and then began producing basically anything an artist wanted—provided it was “their vision and looked like their original work”—from vinyl carpets with Andrea Zittel to silicone dwarf-head sculptures with Paul McCarthy to a pair of silver rings by the late Cuban-American artist Felix Gonzales-Torres, which fetched more than $400,000 at a 2011 Christie’s sale.

“The value my editions went to is shocking, I wish I could have afforded to keep them all,” says Painter today. “Sometimes I gave them away as presents to artists—or traded with them—and looking back I wish I would have just given flowers. They were so good they sold at regular auctions. You didn’t see them in the editions auctions.”

While the business was going gangbusters—so well in fact that in 1996 he staged 20 editions shows around the world—two of his biggest stars (Kelley and McCarthy) threatened to stop showing in L.A. unless he opened a gallery. “I didn’t want to open a gallery,” Painter explains, seated behind his desk and chain-smoking Naturals, which he feverishly chases with Coke Zeros. His neck is wrapped in a skull scarf from Alexander McQueen and he’s dressed all in black save for a pair of white tennis shoes. His short-sleeve shirt reveals a smattering of tattoos—on his right forearm, a knife with a Madonna head and a rosary; on the left, the Latin word vires (“strength in all things”).

“I thought about it, and I was like, ‘I’m Irish-American like these two guys are, maybe god is telling me something.’ So I said, ‘Yeah, I’ll do it,’” recalls Painter. “But the first year I didn’t show any paintings at all because of my name, so I showed Harmony Korine, Dan Graham, Tony Oursler. I wanted to make it really clear it wasn’t a painting gallery.” While wildcards like outlaw auteur Korine set the tone for Painter’s riotous, star-studded openings, where Korine was once sucker-punched by a fan, some suggest the dealer was the real draw.

“For many years Patrick was the show, or as much of the show as the artists were,” says Dean Valentine, who collected heavily with Painter when he was the president of Walt Disney Television. “That matters, because when you’re living in Los Angeles and you have to drive twenty miles to get to a gallery, you want the tour to have been worth it. Patrick added an entertainment value that was really helpful.”

The entertainment didn’t end at the gallery. Painter also redefined the concept of the artist dinner—at least in L.A.—via libidinous bacchanals with late-night dancing at Dominick’s, Mr. Chow and the Avalon Hotel that spilled into the morning hours at his art-filled West Hollywood duplex, where you’d find actors mingling with artists mingling with the dealer’s Irish contingent—tattoo artist Mark Mahoney, who inked much of Painter’s body (including a massive “Irish” on Painter’s back), or Father Greg Boyle, the Angeleno Jesuit who reforms ex-gang members through his L.A. mission Homeboy Industries. “They were in our world, they came to our dinners, and that was part of Patrick’s genius, to take these people from different worlds with different interests and pull them into our vernacular,” remembers Harmon.

Painter’s ability to adapt to any environment started young. When he was six years old, his step-father sent him away from their beachside Greene & Greene bungalow to go to the Southern California Military Academy. His older brother, Craig, drowned in a surfing accident in Hermosa Beach when Painter was one, so his step-siblings—including Greg and Joe Escalante, who became, respectively, a renowned L.A. gallerist and a founding member of the Vandals—were his nuclear family. While Painter remained close with them during his formative years, he grew estranged from them as adults, and Painter says Joe once called him “violent” on his Barely Legal Radio show.

“I don’t remember saying that, but if I did say that, I’m sure I was telling a joke, he was never violent,” says Escalante, who remarked how happy Painter looked when they caught up at the L.A. Art Show in January. The two hadn’t really hung out since Painter’s behavior got the brothers kicked out of a Beverly Hills hot spot in the late eighties. “It was like you were at the last party of Orson Welles’s life when you were out on the town with him. He’s going to order the finest wine, smoke the cigar with the greatest provenance, then start pontificating and name-dropping.”

To wit: Painter often jokes about marching into the New York galleries of David Zwirner and Gagosian demanding money owed from the dealers, and he allegedly hung a Berlin drug dealer out of a window by his belt at the Four Seasons. “I always tried to get arrested for art but never did,” says Painter. Though he claims that “people like to amp up stories on me,” Painter himself may well be the mythologizer-in-chief. “People like to think I’m a gangster, but they don’t even know what a gangster is.”

That might be true, but Painter has always cut an intimidating figure. It probably rubbed off from his father, Virgil Guy Painter. His parents split up when he was two, and his dad, a skilled ad salesman, ultimately ended up in Canada. Despite his absence, Painter became a born closer, just like his father. “I’m a natural salesman,” explains Painter. “At military school, they’d pull me out of class to take parents around to give them a tour. I didn’t get it at the time, but they were actually making money off me.”

As payback, Painter extorted booze from the new recruits in exchange for protection from bullies. By the time he was 12 he says he was dropping acid every other day, and by age 14 he was selling it for the Brotherhood of Eternal Love, an Orange County-based “hippie mafia” that manufactured and sold the lion’s share of the world’s LSD in the 1960s and 1970s. He says that after getting arrested for robbing $100,000 worth of jewelry from a family friend—and facing three years in Chino—his mother pulled some strings, got him out of jail on a day pass, and secured a passport the same day. He was sent to live with his father in Toronto. This north-of-the-border odyssey quickly became its own prison. His father, he says, was abusive. One particularly salient beating occurred after Painter laughed when his dad blamed him forbreaking his watch. In response, Painter says, his father took a golf club to him. Painter soon ran away.

He couch-surfed with hippie friends, but his father eventually found him and put him to work selling magazines door-to-door in Vancouver. He learned to hit his $60 quota in no time but soon discovered the business was a training ground for local mafia looking to burgle and scam unsuspecting customers. Rather than potentially ending up in jail, he opted to get his GED back in Long Beach, then briefly studied business and theater at Loyola Marymount until he was accepted to London’s Royal Academy of Dramatic Art.

“I wanted to know where the money was coming from so I could secure my future,” says Painter, who is still very proud of getting accepted to RADA. But before flying to London, he made a fateful trip to Vancouver and ended up staying after his old magazine boss offered him a “gangster straight” job managing a group of “skimmers” (people who sold subscriptions in parking lots). “I loved being an actor,” says Painter, “but at that point I had some epiphany. I was on the floor from being drunk or on drugs, and I just saw my whole life in front of my eyes, so I bailed.”

The mobster aspects of the Canadian magazine gig soon wore on Painter, and a year in he jumped at an opportunity to sell insurance for MetLife. “It wasn’t the grooviest job, but it was a step up,” says Painter, who quickly became a branch manager and sales trainer. He was living with someone when he met Winnie Fung, who was promoting concerts at the time. “I didn’t know who she was for a year and a half until we went to these dragon-boat races,” says Painter. “I said, ‘Let’s root for your bank, because she had a Bank of East Asia credit card.’ She said, ‘Yeah, that’s my bank.’ I said, ‘Yeah, I got it.’ She said, ‘No, I own the bank.’”

His big break came when he scored a transfer to Paris selling annuities. Due to some internal regulations at the bank, he was basically “getting paid to do nothing,” he says, so with plenty of money and downtime on his hands, Painter decided to check out the Paris art scene. A trip to the Centre Pompidou changed his life forever.

“I saw Twombly first, then I saw this Gilbert and George piece from the Bloody Life series,” recalls Painter, noting the artists’ taunting hand gestures in the chaotic self-portrait perturbed him. “I got in a street fight with this picture. I was pissed. I went back the next day to be pissed at it again, and the next day after that, and I’m like, ‘I think I like the damn thing.’ I thought I was schizophrenic. Then I went to the Left Bank and checked out about twenty galleries and asked everyone about the Gilbert and George: ‘Do you think it’s okay?’” After realizing the “street fight” was simply a profound experience of art, Painter got the bug, and with encouragement from Fung, he started collecting. The couple even took an apartment in New York above Christie’s so he could be closer to the action.

“From the beginning he was very savvy, and I always enjoyed connecting with him, because it’s quite rare that someone comes onto the scene and just gets it very quickly,” says Deitch. “A lot of the new people you might meet, they don’t have a clue, but he’s one of the special people who just got it right away.”

“I just thought it was like shopping, I didn’t even know it would go up in value later,” admits Painter, who became a fixture of the late-eighties auction scene for scooping up gems like a Gerhard Richter landscape for $80,000, which could easily fetch more than 100 times as much today. But in the wake of that 1990 Sotheby’s auction, his reputation shifted from market maker to “the guy who killed the market,” he says. “It was nuts.”

With his relationship on the rocks, he asked Leo Castelli if he would teach him to be an art dealer in 1989. “We didn’t have set hours, I didn’t get paid, but it was a mentorship,” says Painter, who did the same thing a year later on the west coast with renowned curator and Ferus Gallery co-founder Walter Hopps. “Up until I got married, most of my friends were thugs, like bringing semi-trailers full of weed to L.A. and flipping deals with the Hell’s Angels for a million dollars,” he says. “So for me, calling Leo was the natural thing to do. No one in the art world did it, and I couldn’t figure it out. I was like, How do you start this thing and not ask a G in it? And that’s still how I’m talking and thinking.”

Though Castelli would often slap Painter upside the head if he bungled something, he also introduced him to artists like Ed Ruscha, who first met Painter three decades ago in Paris and went on to produce seven photographic editions with the dealer. He also served as the best man—in a brown Gucci tuxedo— at his 2005 wedding at the Hotel Bel-Air to Soo-Jin Jeong, a South Korean athletic trainer who is now the director of the gallery. At their reception, Mike Kelley, Jim Shaw and collector David Teiger danced the night away as the world’s best air-guitar player took the stage. While the party raged until the early morning, in retrospect it might be considered the Nero moment of the Painter empire.

In the years leading up to Painter’s cervical spinal fusion surgery—the result of deteriorated discs—in 2011, after a lifelong run with drug and alcohol addictions, his relationships with many of the artists at the foundation of Patrick Painter, Inc., grew strained. Some of his biggest stars, including McCarthy, who pushed Painter to open the gallery and is now represented by Hauser & Wirth; Shaw, who did six solo shows with Painter but is now represented by Blum & Poe; and Glenn Brown, whose painting career Painter launched and who now shows with Gagosian, refused to be interviewed for this story. Those who did seem to view Painter as a wayward-brother type who despite his estrangement from them, or the art world, they will always consider family.

“Patrick is an art-world original who has an amazing sense for great art and artists,” notes Spiegler. “He was an OG, and even if at a certain point the fairs didn’t make sense for him, I miss his presence at our shows. Today’s art world needs more people like him—and fewer financier types.”

At the premiere party Painter was dressing the part, doing his best to conjure this OG posture of yore. He greeted a steady stream of well-wishers; told insider tales of Hollywood gossip; mugged for a series of event photographers alongside old friends like Chris and Roberta Hanley, the husband-wife producing duo behind Buffalo ‘66 and American Psycho who once cast Painter as an undertaker. While the energy was high, and his new stable of artists were all stoked by the attention—Painter would even secure a promising studio visit for mid-career painter Chaz Guest with Miami-based mega-collectors Don and Mera Rubell—the 63-year-old iteration of this infamous art-world raconteur seemed light years from the Long Beach-born legend who ran the L.A. scene from the mid-nineties to mid-aughts.

“Maybe people saw in him the outlaw guy that mirrored their own outlaw image they had of themselves,” says Butzer, who made his stateside debut with Painter in 2004 but now shows with Nino Mier. “To me, he seemed like a fun guy, and he had some good but eventually some bad humor.”

Over the past six months, when I explained to people that I was interested in writing a story on the improbably named dealer on the heels of his twentieth anniversary at Bergamot, I invariably got one version of the following responses from nearly every artist, curator or dealer I attempted to reach: Why the hell are you doing a story on Patrick Painter? What took you so long? Who is Patrick Painter? He still has a gallery? Is he dead?

In fact, Kenny Scharf, who did three shows with Painter, asked many of these same questions. But when Scharf was having a hard time getting his work back from Tony Shafrazi after 20 years with the New York dealer, it was Painter who used his powers of persuasion to extricate a vault of paintings. “He was a big bully when I needed a bully,” says Scharf, who hasn’t spoken with Painter for years. “I used to like a lot of things about him, and I really liked the artists he was showing. He had his crazy side that would freak people out, but I always thought it was funny. Maybe it shouldn’t have been funny because it had to do with addiction and stuff like that, but it wasn’t politically correct, and that’s what was fun about him. He would fall asleep with a whole plate of fried chicken on his chest in his booth at Art Basel. It was hysterical, that attitude, but in the end his style and what attracted me endedup backfiring and not working for me.”

An old friend and contemporary, Tim Blum, of Blum & Poe, sees Painter as a classic Icarus figure. “He blew up and had a gallery that was second to none with a future as bright and endless as he wished,” he says. “He flamed out brutally and quickly but forever left an imprint on the art world globally, and definitively in Los Angeles.”

To be fair, most of Painter’s financial problems and artist fallouts occurred at a point when his drug habits were at an all-time high and his health at an all-time low. Did Painter fall on financial hardships and make some questionable deals? Yes. Did he alienate a lot of artists and burn a lot of bridges in the process? Sure. “My dad taught me one thing: Never lie to yourself,” says Painter. “I would like to think that no one thought I ever lied to myself or fooled myself.I have a genuine love and appreciation for art and artists. It’s not ‘poor me’ or ‘feel sorry for me’—I think life gives you exactly what you deserve. I guess because of my reputation people wanted to be associated with me up to a point, but after my surgery, did anybody stand up for me?”

Though Painter had dealt with a hitch in his step for years, when he was relegated to a wheelchair at Art Basel in 2010, Soo-Jin threatened to divorce him if he didn’t see a doctor immediately upon returning to the states. Had the physician not admitted him into surgery that night, Painter might very well be a quadriplegic today.

“When they were wheeling me into the operating room they said, ‘There’s a fifty-percent chance you won’t be able to speak,’” recalls Painter. “I said, ‘Wait a minute, if I’m a quadriplegic at least I can sell art over the phone.’ I really had no idea what was going on at that time.” Painter had incidentally donated more than 100 works from his personal collection to the Hammer Museum when he and Soo-Jin were married, and as a result he was unwittingly a VIP at Cedars Sinai. “When you’re going through something like that and you’ve got VIP treatment, it’s like a miracle from god. You didn’t give the art knowing you’d get something like that out of it, but you sure appreciate it.”

That good fortune followed Painter out of the hospital. For the next 136 days straight he claims he sold at least one artwork a day. Ultimately, though, the painkillers became too addictive and he fell into a depression from which he couldn’t emerge. “I got shook, and I had never been shook before,” says Painter. “When you’re always super confident, that’s a pretty big deal.”

It was during this low point that his old friend, the late art advisor Carolyn Glasoe Bailey, whom he met decades ago and dated for a short time, made an unexpected house call. “She looked at me, kind of in that way someone who’s known you for twenty years can look at you,” recalls Painter. “I always trusted what she said one-hundred percent. She says, ‘Honey, don’t you think it’s time for you to stop now?’ I said, ‘Do you really think that?’ She says, ‘I do.’ That really hit me hard.”

Painter ended up at the Betty Ford Clinic, but once he emerged he developed narcolepsy and totally lost control of the business, which was hemorrhaging money with the overhead of three galleries and 32 employees. Thinking he could get a jumpstart from a TV opportunity, he agreed to appear as a dealer/expert on Final Offer, a short-lived Antiques Roadshow-meets-Shark Tank reality vehicle. He thought it would boost business, but artists thought otherwise. He was actually on the set when he got the call about Kelley’s suicide. “That was a really hard thing,” says Painter. “Then I started getting all these calls from the media.”

By the time Painter emerged from rehab, nearly all of the artists he had championed were leaving (or had left) for greener pastures. (Kelley never left his stable, even after jumping to Gagosian in 2005.) To get things back on track he was forced to sell beloved works out of his personal collection from dear departed friends, including Kelley, Kippenberger and Juan Muñoz.

Despite the turmoil—and all things considered, it doesn’t seem possible for a figure like Painter to rise so high so fast without some kind of crash—it appears that the ship is righting itself of late, and despite a recent bout with the flu, Painter seems to be very clear, perhaps the clearest he’s been in years. “I had dinner with him just last week,” says Ed Ruscha. “He’s out and around. He has some health issues, but his game just doesn’t give up.”

Proof of this ride-or-die tenacity can be found in the case of Chaz Guest. Though he’s made headlines with a recent painting of Trayvon Martin and managed to privately sell his portraits of black icons and buffalo soldiers to the likes of Oprah Winfrey, Tyler Perry, President Obama and Quincy Jones over the past three decades, Guest couldn’t break into the art world proper until Painter offered him a solo show last year featuring paintings derived from Guest’s graphic novel Buffalo Warrior, which is now being courted by Hollywood producers.

“I’ve been selling my work all over the world—it’s hung at the White House, and I’ve painted for kings—but I was never in the elite art world,” says Guest, who cites Painter as the only contemporary dealer who saw the value in his work and delivered with connections to collectors like the Rubells. “I just wasn’t reaching those people.”

While the gallery isn’t opening shows at regular intervals and Painter’s name hasn’t been on the tip of tastemaker tongues for a good decade, his eye is still very well regarded by plenty of top collectors. As recently as 2014 he showed (and sold) works from the collection of Blake Byrne, who gave the biggest gift to MOCA in the history of the institution.

“I think he’s a good dealer,” says Byrne. “He’s fallen on harder times, but it’s part of the art world. Now he’s having to start over a bit, but you don’t lose the eye. Today the competition is stiff because there are galleries with lots of capital behind them, and if you’re an individual entrepreneur, it’s a tougher road to hoe. But could he make a comeback?Yeah, he’s got the energy and he’s a likeable guy. He knows his stuff and he’s been around.”

“Evelyn, can you turn off the lights back here because we’re about to cook chickens, man,” Painter yells to an assistant back at his office. While the door is open to the lot where his black Mercedes G Wagon is parked, he’s got a mean sweat on his brow. Through a cloud of cigarette smoke Painter admires a Medardo Rosso bust on a white plinth and explains how he’d like to pair the Italian sculptor’s work—two bronzes from his personal collection—with five ceramic sculptures by New York artist Arlene Shechet.

“I think it’d be a pretty bitchin’ show,” he says, as he directs two assistants to install a Shechet piece—he bought it a decade from his old neighbor, Shoshana Wayne Gallery, out of the artist’s first ceramics show—alongside the Rosso. “I didn’t even know who she was, but it reminded me of Bruce Nauman’s wax cats. It really has a good vibe.” He asks his assistant to take a photo of the works together and send it to Shechet as a pitch on the concept.

“That’s a good idea,” Shechet told me over the phone. She never received the pitch and is working toward a fall show with Susanne Vielmetter Los Angeles Projects, but says, “I’m a huge fan of Medardo Rosso. I think there’s something one-hundred-percent correct about his pairing. I’m currently showing with other people in L.A., but that doesn’t mean a great historical show couldn’t be interesting.”

Painter is also looking at new gallery locations and is in talks with some well-known New York and L.A. artists (including Zoe Crosher) about restarting the editions business. He’s even stalking some old outlaw contemporaries like Bali-based art star Ashley Bickerton, who is considering a move to L.A. and possibly showing with Painter, whom Bickerton calls “the been-there-done-that guy” who has “fought the wars in the trenches.”

“I think if he were just arriving and developed a company and roster like he had, he would crush it, frankly,” says Tim Blum. “Anything is possible, and if he got his act somewhat together, plenty of folks would line up for the ride!”