DeMar DeRozan spent the first nine seasons of his career with the Toronto Raptors, becoming a beloved figure within the organization.

So when he was traded to the San Antonio Spurs ahead of the 2018-19 season, he was devastated, as he revealed on The Pivot Podcast Tuesday (25:10 mark):

"It f--ked me up, I'm being honest. It's crazy. I'm more than comfortable talking about it now but for the longest time it f--ked me up because, one, that was the place I wanted to be, thought I was going to be, gave everything to. Like my whole motivation and drive was to simply put Toronto on the map. I wanted to follow the whole motto of, you know, Kobe [Bryant], my favorite player, I wanted to play on one team. I had it all mapped out. So when I got traded it was such a blow because at the time I was dealing with my family stuff, like you said, that was when my dad first started getting sick. That was the first time in my professional career where I just felt like out of it, I felt lost. I started to question every single thing."

DeRozan said the night he learned of the move, he was sitting in a movie premiere for Equalizer 2, just down the row from Denzel Washington. He said his phone kept blowing up during the movie and when he left the theater got the call that he had been dealt.

"I didn't tell nobody in the car what happened when I got the phone call," he added. "I just told told dude to stop the car. I got out the car, started walking. I just walked down the street, sat in front of a fast food restaurant and I, like, I just start crying. Like, I just I couldn't believe it."

The Raptors traded DeRozan, Jakob Poeltl and a protected 2019 first-round pick (which eventually turned into Keldon Johnson) for Kawhi Leonard and Danny Green. It was the most important trade in Raptors' history, resulting in a title for the team in the 2018-19 season.

The good times didn't last long in Toronto—Leonard signed with his hometown Los Angeles Clippers in the summer of 2019 and the team has won just once playoff series since. But banners are forever.

As for DeRozan, he spent three seasons in San Antonio before moving on to the Chicago Bulls in a sign-and-trade deal in 2021. It proved to be a fantastic decision—he's averaged 25.5 points per game over the last three seasons, with two All-Star berths mixed in.

Granted, the Bulls only made the playoffs once in his three seasons in Chicago, failing to advance past the Play-In Tournament in each of the last two years. But it's been a positive third act after the transition from Toronto to San Antonio was a difficult one for DeRozan.