“Check,” I say, sliding my white queen across a few inches of plastic chess board. Tee Grizzley laughs, blocks my attack on his king with a knight, and announces, as if to an audience of groveling medieval courtesans, “The check, indeed, was frivolous!”

Not so fast: I swing my own knight up from the wings. “Check.” He looks at the board and furrows his brow. “Ooowee!” he exclaims, appraising the situation. “He got me together right quick.”

After spending most of the game on defense against Grizzley’s systematic onslaught, I’ve found an opening. My knight has “forked” his king and queen, requiring him to move the former and allowing me to capture the latter.

“It's interesting that you would do that,” says the Detroit rap sensation, who plays chess the way some people play one-on-one basketball: accompanied by a stream of jovial shit-talk. “I didn't take you for the kind of person who would try to play with me like that.”

I push the advantage, moving my queen further up the board to chase his king. Big mistake — I’ve ignored a lurking bishop, and now it’s payback time.

“You ain't done yet,” he says as he snags my best piece, adding, in a hammy stage whisper, “But you will be!”

A few minutes later, after Grizzley’s finished roasting my error and mincing my defenses, I am.

“You know what you did wrong?” he asks, as I tip my king over.

“Started playing me!”

My ignominious defeat takes place in the drab conference room of a Hilton in King of Prussia, Pennsylvania, where Tee Grizzley has traveled at the invitation of Gloria Carter, mother of JAY-Z (an avowed Grizzley fan). Ms. Carter runs the Shawn Carter Foundation, an organization dedicated to helping high schoolers from tough backgrounds pursue higher education.

To that end, she’s spent the previous week leading a group of a few dozen students from New York City on a whirlwind tour of HBCUs up and down the Eastern Seaboard. For their last day, she’s booked something special — a lesson in chess and life from an artist who knows his fair share about both.

When I arrive at 10 a.m., the students are already there, seated around conference tables with chess boards, wearing shirts that read “College Bound.” They’re in the middle of an introduction from a rotund chess instructor, who, having run through what each piece does, is now fruitlessly trying to explain the game’s arcane system of algebraic notation. Kids stifle yawns and check their phones. It is, as they say, too early for this.

Then Grizzley appears. The room erupts in cheers; teens start playing his songs off their phones and streaming on Instagram Live, bringing friends and family into digital proximity with the star. He walks slowly to the front of the room, giant bear claw chain glinting under fluorescent lights.

“In chess, you gotta come up with a strategy,” begins Grizzley, after Ms. Carter shushes the crowd. “I made a lot of plans in my life. I’ma do this, I’ma do that, this is gonna happen, that's gonna happen. And a lot of stuff don't go as planned. You really gotta act on events as they unfold. That’s how I compare chess to life.”

This might sound like vague motivational boilerplate, but the 24-year-old is referring to a specific disrupted goal, the same one his audience is now pursuing: a college degree.

Grizzley grew up on Joy Road on Detroit’s West side. “People killed people every day,” he recalls, later that morning. He was close with his uncle, who was involved in gang activity. “There used to be real hitmen in my neighborhood, real killers. And he used to go to war with them.” His uncle’s fearlessness motivated him to pursue his dreams at all costs, and what he dreamed about was higher education. “If he's not scared to go after that, damn, I could go up to college and say, ‘I'm gonna do better than anybody’,” he remembers thinking.

Throughout high school, Grizzley studied hard and steered clear of violence and drugs. His life outside the classroom was far from easy — in 2011, his mother was sentenced to fifteen years in prison for drug trafficking. The following year, his father was killed. But he never gave up on his ambition, and in 2013, he enrolled at Michigan State, majoring in Finance and Accounting. He was the first person in his family to attend college, and he loved it. “So many resources, so many good people, it was real diverse.”

But by the end of his freshman year, Grizzley ran out of money to pay for school. In February of 2014, he and another student were arrested for stealing cash and laptops from the dorms of fellow students. After his release on bail, with a trial pending, he fled to Kentucky, where he was arrested after the owner of a jewelry store he was attempting to rob pulled a gun on him.

“In Kentucky, it was like, I’m about to do this for some lawyer money for the case I got in Michigan,” he told XXL. “Basically, I just needed some money and had to do what I had to do.”

After the second arrest, he landed in prison back in Michigan. It was there that the rapper first encountered chess. He learned from an older guy who “could not be beat,” he recalls. “He was cold-blooded. Wouldn’t give you a single pawn for free.”

Soon enough, Grizzley was playing for money. He rapidly elevated his game; there’s a “real high level” of chess in prison, he notes, and real consequences. “You could get butchered over chess.”

Chess is a game of feints and sacrifices. But it’s also about meeting force with force, calling the bluffs of opponents who mask weak strategy behind an overconfident offense (case in point: my doomed queen). After his arrest, a prosecutor offered Grizzley a deal. He could plead guilty to a series of charges carrying a ten-year sentence, or face up to 30 years if convicted. On his breakout single “First Day Out,” Grizzley memorialized his response: “I told them crackers holla at me when they sober!”

“This was my thought process,” he explains. “The same people that's gonna die in ten years, which is my grandma, my granddad, most of my old relatives, the same people that's gonna die in ten years are gonna die in thirty years. That's like coming home with a new identity, like plastic surgery. Nobody’s gonna know you.” Grizzley fought the case and was sentenced to 18 months behind bars.

Looking back, he feels like incarceration gave him an opportunity to reset. Grizzley started reading voraciously: “I read autobiographies, I read dictator's handbooks, I read real estate books, I read hood novels, science fiction books.” (His favorite: Rich Dad, Poor Dad.) Prison also gave him the time to write his debut mixtape My Moment; he filmed the video for “First Day Out” on his actual first day out.

Back in Philly, Grizzley concludes his speech with a long digression about the value of a four-year degree in today’s job market. “You all filled out your FAFSA?” He asks. A chorus of voices answer, “Yup!”

“Good, that's free money!”

Then he traverses the room, taking on all challengers in quick chess matches. Most of the kids have never played before, but one girl from the Bronx — who picked up the game while in a suspension program at school — is a strong opponent, both in strategy and banter. “You could be my protege,” quips Grizzley, after taking her queen. “I would have beat you if people weren’t watching!” she responds.

Later, while Grizzley poses for photos, Ms. Carter and I chat about the program.

“These kids need to know about making mistakes and changing their lives,” she says. “When they first come in, they see chess boards, and they're like, ‘Oh I don’t think I wanna do this…’ Bringing somebody that struggled and then used chess to become a better person, it gives them incentive. They’re not gonna stop playing here. They're walking out with chess sets, so when they go home, they're gonna play chess.”

After the kids get back on the bus and head home, Grizzley and I play a game. I ask if he’s drawn to chess because it requires the same kind of shrewd risk vs. reward analysis he’s employed throughout his life, whether in prison, Detroit, or the music industry.

”Yeah, I would say that.” He moves a rook.

Checkmate.