Desouza loved to act growing up in Baltimore, but when push came to shove he knew getting a computer science degree at the University of Maryland was the more sensible option. It’s not that that path wasn’t fulfilling, he says; “I was a software engineer. I was like writing codes and apps and all that shit,” he says. But he really wanted to act. So he quit his job coding, got a real estate gig where he could make his own hours, and readied himself for what he believed was going to be a very long grind: years or even decades before he got his first big break, with a lot of Megabus rides from Baltimore to Manhattan and back ahead of him. “I was going back and forth to New York at three or four AM to get into the city by eight or nine in the morning so that I could audition for Law & Order or something,” he recalls. “Then get back home by five in the afternoon.”
Not quite a year after quitting his day job, Desouza stumbled into his big break. He saw HBO was casting for a role “for this basketball player, six-foot or above with some acting and basketball skills.” He sent in a tape and within a week he was on a Skype call with McKay and the show’s other producers. The young actor chopped it up with them for about 15 minutes and went on his way. Desouza was used to that. What he wasn’t used to was hearing the words McKay left him with: “Just know as of right now you didn’t fuck anything up.”
McKay told him it could be some time before he’d hear back, but then a few weeks later the call came through: he’d scored his first major role. Of course there was one big thing he had to do: he had to learn to really play ball. Winning Time is about basketball players, and becoming a basketball player—a pro basketball player, not a pickup one—took practice. Lots of it. “Three hours a day, five days a week,” Desouza says. It was conditioning for the first hour, then skills stuff, everything from shooting and passing to the fast breaks the team was famous for. “It was a pretty rigorous process,” he recalls. But the point of it all was to make sure they got everything right—to make sure Hughes had Kareem’s skyhook and Isaiah could toss a perfect no-look pass. Desouza focused on his footwork, to make his jump shot look exactly like Cooper’s.
But his primary challenge was a little tougher: Michael Cooper is right-handed, while Desouza is a lefty. During the first practice, the actors were introduced to Idan Ravin, the longtime basketball skills coach (he’s worked with everybody from Steph Curry to Kevin Durant) who was tasked with getting the actors into shape. Ravin looked at Desouza dribbling with his left and asked him to switch it up. “So I grabbed the ball and I shot it and he stared at me for a few seconds and he said, ‘Wait, you’re left-handed? And I said yeah. He said ‘that’s a problem.’” Fix a problem like that means putting in even more work. “We had to practice for two years before we even started shooting the show,” Desouza says. “We would wake up at seven or eight A.M. to go to practice.” When they took down the rims off public basketball hoops in Los Angeles at the start of the pandemic, Desouza and his team kept showing up. “We were just shooting the ball against the backboard,” he says, their skills coach Zooming in from a laptop on the East Coast.