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.”