Toronto. Or, as the locals call it, “The 6ix”.
The nickname was popularized by the world-famous rapper Drake, one of the most influential figures to ever come out of the city. The Canadian artist has always been closely connected to his hometown and, since 2013, has also served as the global ambassador of the Toronto Raptors.
Drake rarely misses a big Raptors night. He is often sitting courtside, hyping up the team, celebrating every big play and living every moment like a true fan. And during Kawhi Leonard’s unforgettable stint in Toronto, the two built a special bond.
“The Klaw” made history with the Raptors in 2019, leading the franchise to its first-ever NBA championship and earning Finals MVP honors. Drake was there every step of the way, celebrating one of the greatest seasons in the organization’s history.
Kawhi Leonard and the Toronto Raptors are expected to start extension talks this week -- and the two-time Finals MVP will do so with new representation. Leonard has hired Harrison Gaines, Esq. of SLASH Sports as his new agent.
— Shams Charania (@ShamsCharania) July 6, 2026
ESPN Story: https://t.co/5n0D0vR4dJ
The two shared plenty of iconic moments together. Their connection was never hidden, with Drake constantly hyping Leonard up, even during warmups before games. But their time together in Toronto came to an end when Kawhi decided to sign a three-year, $103 million deal with his hometown team, the LA Clippers. And honestly, how do you say no to that?
Still, the bond between them never really disappeared. Drake and Leonard kept hanging out, while Kawhi even made a memorable appearance in Drake’s 2021 music video for “Way 2 Sexy”, alongside Future and Young Thug. It instantly became a hilarious easter egg, with Leonard dancing awkwardly and staring at the others in classic deadpan fashion.
Now, seven years after his incredible one-year run with the Raptors, the 2019 Finals MVP is finally back in Toronto, chasing the possibility of another magical chapter.
But as much as his return to the Raptors has fans excited, the internet seems just as hyped about one other thing: Kawhi linking up with Drake again.