He turned his prison chess hobby into a wild street hustle. But can he beat the elites?

Almost every day for the last two years, Vincent “VDogg” Hubbard has stood outside the Louisiana Fried Chicken at Manchester and Normandie avenues with a suitcase full of cocoa butter and a traveling chess set.

Slight in stature, with a gap-tooth smile and a blunt tucked into his beanie, the 44-year-old is South L.A.’s preeminent purveyor of everything from African black soap to charcoal toothpaste to bundles of sage. But if you’re a chess enthusiast, you’re more likely to stop by for an over-the-board “a— whooping,” where he’ll snap up your pieces with a side of smack talk before “leaving ’em with two pieces to go.”

“Just without the chicken,” he chuckled, while scanning the dinner rush for potential customers or competitors. “And I usually have ’em before their order’s up.”

As part of the tight-knit street chess community below the I-10, Hubbard is one of many formerly incarcerated gang members who used to play in prison to barter for contraband items or commissary goods. While others may drop the game upon release, chess continues to play a huge part in his life as a viable source of income in a job market that turns its back on people who’ve done time.

Vincent Hubbard poses for a portrait outside his friend’s party bus in South L.A. Hubbard perfected his chess game serving a 10-year prison sentence and now is trying to turn his skill into a career. He’s found it hard to find a job that will hire the formerly incarcerated.

(Jason Armond / Los Angeles Times)

Hubbard packs up his chess board and belongings after spending the afternoon playing chess outside of the Louisiana Fried Chicken.

(Jason Armond / Los Angeles Times)

Hubbard usually measures his wins in $20 bills, earned from speed games against a curious onlooker or a cocky passerby. Unlike the regulars, they don’t know his losses are in the single digits, only that he looks like “a real thug from the ’hood” until he begins to attack, quickly picking off pieces and relentlessly checking his opponent.

“I’m on your head like hair,” Hubbard said, recalling a recent game against a flustered opponent.

“I’m coming out with missiles and whatever. I’m coming out strong,” Hubbard said, playfully boxing the air. And with his unfettered confidence, natural talent and unconventional play style, Hubbard wants to make it known that “nobody could f— with me.” In his mind, not even five-time world chess champion Magnus Carlsen.

After all, he’s already squared off against titled players and is a two-time champion of South L.A.’s Make a Move, but there’s a big difference between winning an amateur tournament like that one and being recognized as a professional player in the highly competitive chess world.

Hubbard is already a pro in the eyes of the United States Chess Federation, but if his ultimate goal is to be one of the very few to make chess a full-time job, he’ll need to receive a certified rating. Culled from the results of several tournaments, his rating will determine how much he can charge for lessons and whether he’ll be able to compete in certain competitions, where the prize money can be in the millions.

Hubbard — a self-taught player — started that path in October by competing in his first rated tournament against established professionals from the Santa Monica Bay Chess Club. It’s a small classical tournament, where one game can last upwards of six excruciating hours. The competition is fierce, mostly motivated by ego and ratings rather than the $200 prize. That’s less than a weekly grandmaster lesson or the entry fee for the upcoming North American Chess Open. For Hubbard, though, that money could be food or more merchandise to sell. It could be rent for the house he shares with several other people waiting for Section 8 vouchers. It could even be the bus fare for the two-hour ride from South L.A. or the $25 entry fee for the club’s next tournament, which he needs for experience if he wants to keep moving up in the chess world.

Vincent Hubbard sets up outside of the Louisiana Fried Chicken for $20 speed games. (Jason Armond/Los Angeles Times)

Vincent Hubbard says he learned chess on his own so doesn’t play like others who were taught specific maneuvers. (Jason Armond / Los Angeles Times)

Chess offered escapism in prison

Born and raised in the Jordan Downs housing project in Watts, Hubbard spent his childhood bouncing between foster care, older relatives and juvenile hall. Initiated into the Grape Street Crips the first day of junior high, he spent his young-adult years in and out of L.A. County Jail, where he realized chess was not only “a good way to pass the time” but a way to obtain some of his favorite snacks, whether they be noodles or Little Debbie’s oatmeal pies.

However, things took a turn when he was arrested in Oklahoma on drug-trafficking charges in 2000, just three days shy of his 21st birthday. Sentenced to 10 years in the state penitentiary, Hubbard perfected his game over the next decade, studying Aron Nimzowitsch’s “My System” and playing correspondence chess with other inmates.

“In maximum security, we’d draw a board and then shape tissue with water into the pieces,” he said, explaining that he’d send messages containing his moves via old chewing tobacco cans, thrown “24 cells down from the dude I’m trying to play.” And with not much else to do, Hubbard used chess as his “PlayStation,” a mental escape from prison life where he could focus on a singular goal — checkmating his opponent — by finding innovative ways to adapt to unexpected situations or setbacks.

“Chess is an outlet, and it’s a way for me to use my brain,” he said, adding that he eventually became known as the Oklahoma State Penitentiary’s “Evil Emperor.” With his ability to conquer the chessboard, Hubbard would immerse himself in the game, spending countless hours in his cell, treating his makeshift pieces like “those little feudal societies where the king’s gonna take over other kingdoms.”

He snickered, “I’m out there in the South, and I’m like, ‘Come through. Who thou plays me thou peasants?’”

In addition to playing $20 street chess, Vincent Hubbard also sells goods like cocoa butter, which he carries along with his chess set.

(Jason Armond / Los Angeles Times)

Between these little quips and his winning streak, Hubbard is a beloved and well-respected figure within the street chess community, said Make a Move tournament founder Jerimiah Payne.

“Everyone loves V’s charisma, and it’s really good to see somebody like that in these kinds of spaces,” said the West Adams-raised player, who began the roving event as a more “comfortable” alternative to other L.A. chess events, which can feel unwelcoming to outsiders.

“[It’s for people] from the neighborhood that would probably never compete at one of those other chess tournaments, like the … rated ones,” he said. Because, contrary to stereotypes, Payne explained that chess is a “great unifier,” before adding that Make a Move was partially inspired by seeing Bloods and Crips play together when he went to jail for burglary.

At its core, Make a Move is a love letter to the street chess community, cultivating an environment that mirrors the players’ welcoming attitudes and willingness to help one another grow. Yet despite its increasing popularity within the L.A. chess scene, Hubbard said the warmth has rarely been reciprocated when he walks into an “established” chess event. Rather, he feels a palpable chill in the air. “People be clutching their purses or their wallets when they go by. You see their body language, freezing up,” he said. To him, the message is clear: You shouldn’t be here.

Vincent Hubbard competes at a tournament hosted by the Santa Monica Bay Chess Club at St. Andrews Lutheran Church.

(Jason Armond / Los Angeles Times)

Breaking in as ‘the black sheep’

“When you think chess, you think of class and prestige … respect and nobility,” Hubbard said, alluding to how he’s constantly underestimated by more affluent players.

The microaggressions happen irrespective of setting. At casual meetups in bars and cafes, they’ll inch closer together, avoiding direct eye contact in favor of pointed whispers and sideways glances. At the tournament, the room goes silent and everyone stares when they think he’s not looking, especially the helicopter moms waiting for their chess prodigies. Everyone seems both curious and afraid of what could be inside his suitcase.

“[I’m] the black sheep,” Hubbard shrugged. “But I’m used to being the bad guy in the movie anyway.”

It’s “TenTrey Day” — the biggest holiday for Grape Street Crips — and Hubbard is completely “graped out” to represent his roots at the Santa Monica Bay Chess Club tournament. Dressed in head-to-toe purple, he’s easy to spot inside the beige meeting room of a small Sawtelle church, with his bright bandanna and matching camo pants and T-shirt. This time, everyone seems too scared to look at him, even when his back is turned.

For this game, it’s his turn to play black pieces, which move second and, theoretically speaking, lose more often than white. The obvious symbolism doesn’t escape Hubbard while he’s outside taking a mid-game smoke, watching his opponent ponder their next move. Coincidentally, his competition is also in a purple shirt, which Hubbard finds almost as funny as the old man who tosses a barely smoked cigarette into the gutter to avoid him.

He makes a teasing comment about the other man’s eagerness to run back inside. It’s like the way he used to speed-walk to the other side of Watts, just to learn basic chess moves on a church computer. The only difference, he laughed, is that he was getting chased through rival gang territory.

“I had to figure out all the other s— for myself, honestly,” Hubbard said. He sounds tired, his voice missing its usual bravado as he admits to having a rough start to the tournament. He’s won one game and drawn another and, after a particularly disheartening defeat, he even skipped a round to save the last of his cash, opting to play on the street instead, “because why show up if I’m gonna lose anyway?”

“A lot of these dudes, all they do is study lines. They read books. Some of them got photographic memories,” Hubbard said while nodding toward the tournament hall.

“Whereas on the street, or in the ’hood, or whatever, the average player just plays,” he explained. “They don’t understand the intricacies or the fundamentals of chess,” Hubbard sighed. “Chess is so simple but complicated. It’s easier said than done.”

While in prison, Vincent Hubbard crafted chess pieces out of paper towels and water. Now he hopes to turn chess into a career by competing in competitions and teaching others.

(Jason Armond / Los Angeles Times)

Evolving from a pawn

However, fellow street player and Hubbard’s longtime family friend, William “Chill” Somerville, used a more apt allegory to describe their intertwined chess journeys, explaining that everyone forgets a pawn’s innate potential — the power it has once it crosses the board.

“If you make the right moves in the right steps, it can become a rook, it can become a queen, it can become a bishop,” he said. “And life is like that.

“So if you make the right moves and steps, then you can be bigger than a pawn. Even if they looking at you as one,” he continued, before explaining that this is why the two decided to create Prolific Chess, a new organization that aims to make the game accessible to everyone from schoolkids to people living on Skid Row.

With a gentle demeanor and a sprinkle of gray in his beard, Somerville similarly fell in love with chess in L.A. County Jail. While he was being held on two charges of attempted murder prior to his acquittal, chess became a way to “relax,” to create and think outside of the box, which ultimately helped him realize, “You’re bigger than what you’re looking at.

“You’re bigger than what the people say you are,” he said, almost like a mantra. “You’ll become what you want.”

Since then, he’s become a Watts community ambassador and mental health advocate who wants to help people gain confidence from chess. So after years of playing against Hubbard in a shipping container on the empty lot next to his house, Somerville refurbished a party bus with a stripper pole and alligator skin upholstery into a suave mobile chess center. He brings chess tournaments, workshops and seminars to every corner of South L.A. through Prolific Chess.

Vincent Hubbard takes a smoke break during the Santa Monica Bay Chess Club tournament. After this one, he’ll have to keep competing to solidify his official rankings with the U.S. Chess Federation.

(Jason Armond / Los Angeles Times)

For both men, chess was a lifeline during hard times that turned into a lifelong passion. And now, Hubbard hopes to break further into the professional chess community so that he can build a career that extends beyond the streets. He has a provisional rating with the U.S. Chess Federation that puts him in the 80th percentile of members, but he must keep competing for that rating to become official.

“I represent a lot of [the] misfortunate, or underprivileged, or have-nots,” he said. “Regular people out here that might not have opportunities.

“So when I’m playing chess, I’m representing everybody in my neighborhood. Everybody in my city … Wattsangeles.”

Hubbard smiles down at his phone, looking up which bus will take him back to South L.A. “Because how many people there get to say that they play chess, and that they’re now a professional?”