The Baltimore kid who gave 'Winning Time' an underdog soul

When the season finale of the controversial HBO series “Winning Time” aired last week, it garnered more than 1.6 million viewers across platforms. Jerry West very likely wasn’t one of those viewers. However it wouldn’t be a reach to believe the NBA legend’s criticism over his portrayal in the show — as a tempestuous and profane malcontent who vacillates between anger and despair — helped boost ratings.

Count me as one of the curious. I tuned in all for 10 episodes. As a snobby sports fan, at times purely hate-watching just to nitpick the show for taking creative license as it retold an already dramatic story laid out in Jeff Pearlman’s book, “Showtime.” How convenient it is in episode 5 that a baby Kobe Bryant just happens to be in the stands when his dad’s team plays the Los Angeles Lakers in Magic Johnson’s rookie debut. And sure, let’s all suspend disbelief as the 1979-80 Lakers took that make-or-break Christmas road trip to Indiana, Detroit and Boston in episode 7 — when in reality they played in Kansas City and Utah before returning to the Fabulous Forum on Dec. 28 for the big Magic vs. Bird showdown.

There are many more moments that make you want to watch every episode as an unofficial fact-checker, but then there are scenes like the one in episode 6 between veteran actor Wood Harris and newbie Delante Desouza.

Two years ago, Desouza, a Baltimore native and University of Maryland alum, had never heard of a pick-and-roll — “I would’ve thought: ‘Oh, a football pick, like an interception. And then a roll, I guess a roll to the touchdown, like the goal line,” he told me, laughing at his limited sports knowledge.

But here he is playing Michael Cooper, one of the more earnest characters on a roster filled with superstars, and he’s stressing inside a hospital waiting room about his future on the team.

Harris, the actor who portrays Spencer Haywood, notices his teammate’s glum demeanor.

“Brotha, I ain’t know you but a minute but what I can say is you are the nervousest cat in a building full of people who are dying. Didn’t nobody end up in the NBA by accident.”

Desouza as Cooper: “I don’t know, Spence. Maybe I’m the first.”

“No, you not. You’re supposed to be here, you understand?”

In that moment, there was truth.

Desouza, 27, had every intention of making a career in computer science and being the one in his family to break beyond the poverty line. The son of a Jamaican immigrant who delivered the Baltimore Sun and a public-school employee who assisted special needs children, Desouza remembers his family not having much while growing up in northwest Baltimore. So it was a big deal when his father saved up money and brought the family a home computer — Windows 98, you could play Minesweeper on it.

Socially fearful and painfully shy, Desouza wasn’t much for going outside and playing ball, so he took to the computer. By the time he got to College Park, he settled on computer science and thought his life was set, until he joined the workforce and discovered he hated his job.

“Computers and software development was a hobby, not a passion,” Desouza said.

Around the same time his father purchased the computer, a then-14-year-old Desouza had stumbled into acting. He joined the Arena Players, which boasts of being the longest operating African American community theater in the nation. And this being Baltimore, he had Robert Chew, who played Proposition Joe from “The Wire,” as one of his acting coaches.

Before leaving for college, Chew reminded Desouza he had a knack for acting. Years later, when Desouza realized his true passion was the stage, not software, he started taking 4 a.m. Megabus rides to New York City for auditions. On the bus, he’d fire up his laptop because he wasn’t taking off days from work, and then arrive in the city to read off lines in whatever cop procedural was casting at the time.

“It was a crazy grind,” Desouza remembered.

Desouza made that trip about 15 times and never booked a gig. His IMDb page looked exactly like mine — blank. It wasn’t until the summer of 2019 that Desouza was scrolling an actor’s website and came across an open casting call looking for a Michael Cooper type: someone 6 feet or above, who played basketball and was shaped like a beanpole. Desouza filled two of the three categories — the man knew nothing about basketball, remember? — but looked at Cooper circa the ‘80s and noticed an uncanny resemblance. Despite his lack of basketball knowledge, he sent in a headshot and a video of himself pretending to play the game, even though he’s left-handed and Cooper is not.

“And it was terrible,” he said.

Still, the show’s producers looked past all that and saw Desouza as Cooper, their lob-catching, defensive dynamo who worries about making the team. When Desouza stepped on set, he said, he embodied the same anxiety of his character.

Though other newcomers such as Quincy Isaiah (Magic Johnson) and Solomon Hughes (Kareem Abdul-Jabbar) make splashy debuts, the show features an ensemble cast of heavyweights, including Sally Field, Adrien Brody, John C. Reilly and Harris. Not to mention that Adam McKay, the producer and director behind “Succession,” “The Big Short” and “Anchorman,” was yelling direction into a megaphone on Desouza’s first day on set. In a scene shot for the show’s pilot that was ultimately cut, Desouza had to play basketball with Isaiah in front of 600 extras.

“I’m about to have a nervous breakdown,” he recalled.

The anxiety in doing his first project, and fear of not being able to keep up with the actors, powered Desouza’s scenes when Cooper was feeling nervous about getting cut or falling out of the coach’s favor. But the man who didn’t know what a pick-and-roll was made it look believable during episode 7 when Cooper set a screen for Magic and received the ball back to make the game-winning layup.

Of course, this never happened in the real game. That season when the Lakers defeated the Celtics in Boston, Norm Nixon’s free throws with three seconds remaining made the difference in the 110-108 win. Those kind of liberties can make a sports fan roll their eyes — and if you’re Jerry West, demand a public retraction.

Most of the Showtime Lakers and current brass want nothing to do with the show, probably because the narrative plays up their part in the wild, wild west days of the late ‘70s and early ‘80s (Reilly as the late Dr. Jerry Buss is equal parts Austin Powers, Hugh Hefner and Creepy Dad you wouldn’t bring your girlfriends home to meet). So Desouza takes his time when answering the criticism the show has received from some of the living legends it depicts.

“The thing is with the entire show,” Desouza said after taking a beat. “I mean, first and foremost Jerry West, he’s entitled to his opinion about his portrayal on the show. Whether that be a positive opinion or a negative opinion. Just like Magic and Kareem and everyone who’s spoken publicly about how they feel about the show. All of their opinions are very much valid. The thing about the show — and HBO has come out and said this — ‘Winning Time’ is not a documentary. It’s a fictionalized work of art.”

He continued.

“The reason I feel personally that some things are changed or some things are embellished is because we were just trying to encapsulate all the facets of humanity within these prolific people,” Desouza said. “And present it to an audience to one, make enjoyable TV, but two, make people fall in love with these characters.”

Which is why it was easy to fall in love with Desouza’s Cooper. There is a story beneath all the fictional game results, the glitz and gluttonous behavior throughout the show. The story of a businessman (Buss) building an empire, a player (Magic) longing for respect, a coach (Jack McKinney) fighting for his life’s work and even an everyman like Cooper, trying to keep up. It is the story of strivers, and Desouza — the Baltimore kid turned computer science graduate and now enchanting co-star — adds every sports fan’s character to this Hollywood creation: the underdog.