The 2019 NBA playoffs saw the Toronto Raptors win their first-ever title behind first-year head coach Nick Nurse and league superstar Kawhi Leonard. Their title run was full of memorable moments, including Kawhi Leonard's four-bounce rimshot buzzer-beater to sink the Sixers in the second round. The Raptors would eventually win the title with a 4-2 series win over the Golden State Warriors.
Meanwhile, Drake became a persistent figure on the sidelines, cheering on his hometown team. Drake has an interesting history with Toronto sports. A string of failures by teams from the Canadian city, often after Drake was in attendance or shoutout the team, has led fans to declare the rapper to be cursed. However, not only did the Raptors win the 2019 title, but Drake also tormented a then-owner of the Sixers with some masterful trolling.
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Drake Had "No Chill" After Game 7 Buzzer-Beater
Appearing on the All The Smoke podcast, Michael Rubin, who owned a stake in the Sixers between 2011 and 2022, revealed just how much Drake had trolled him. “My worst memory of Drake is in the middle of Game 7 of the playoffs, he sends me a picture of himself wearing Sixers shorts. He said, ‘I’m coming for you,'” Rubin recalled. “As soon as I saw him in Sixers shorts, I said, ‘We’re losing this fucking game.’ That jinx-ass muthafucka. Just put on these shorts and I knew it was a wrap." Rubin was right, of course, as Kawhi Leonard ended the game with the aforementioned four-bounce buzzer-beater. However, Drake was not done with Rubin.
“By the way, I’ve never seen someone FaceTime me more times and me ignore him more than after that game. He had no chill. We had just lost [to Kawhi’s shot] and he FaceTimed every two seconds. I just never picked up. I just went home depressed.” The pair apparently quickly reconciled, with TMZ spotting them gambling in The Bahamas after the Finals. However, Drake would also go on to reference Rubin in "When To Say When" on Dark Lane Demo Tapes. “I watched Michael Rubin win a million off a couple hands/ I decide what to see next like it’s on demand/ I decide what to be next like I’m switchin’ plans/ I’ma tell you what you feel next like the weatherman."
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