The DeMar DeRozan trade from the Toronto Raptors to the San Antonio Spurs back in 2018 still remains to be one of the most shocking transactions in recent memory. The Raptors did end up the big winners of that trade after Kawhi Leonard led the team to its first NBA championship in franchise history. However, there’s no denying that the sacrifice it took to achieve this ultimate goal remains to be a hard pill to swallow for Toronto fans to this very day.

DeRozan was the Raptors’ long-time servant and he was absolutely loved throughout Canada. Not many saw this trade coming and it caught most of us off guard. The same can be said for DeRozan himself, as well as former Toronto teammate Kyle Lowry. According to Lowry, who now plies his trade for the Miami Heat, DeRozan was in an utter state of shock when they spoke on the phone moments after DeMar learned about the trade:

“I was distraught,” Lowry told Tyler R. Tynes of GQ. “Because he was really distraught. That’s my brother. I ain’t talk for like five minutes—just sitting there with him on the phone. You don’t know what to say; he never thought he would be traded. For both of us, it was like, ‘Goddamn!’”

That would have been a really awkward phone conversation and an undeniably heartbreaking one as well. DeRozan and Lowry spent many years together as teammates with the Raptors and they’ve been through so many battles together on the basketball court. They developed quite the friendship off of it as well, which made their parting of ways even more difficult.

Lowry knows that this was all part of the game and that at the end of the day, the NBA is a business. However, the Heat guard could not help but express the betrayal they both felt at that very moment:

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“S–t happens,” Lowry continued. “But, for him to have poured so much into a country, a city and a franchise, where guys didn’t wanna go and didn’t want to stay, and he’s pouring his heart and soul into that? It hurt.”

DeRozan himself opened up about that unforgettable moment and you can almost feel his emotions based on his heartbreaking account:

“It was one of those moments, that was just like, ‘What the f–k?!’” DeRozan says. “It was a hit. It was heavy. I felt everything, anger, resentment, frustration.” He felt connected to Toronto—really, truly bonded in a way that transcended the contract he’d signed—and it was being taken away from him. “Every emotion you could think of negatively, I felt that. It took me a long time to figure out.”

Lowry ended up winning a chip with the Raptors right after DeRozan left. He’s now with the Heat, who are considered to be one of the top contenders in the East. The same can be said about the Chicago Bulls, who have been on an onslaught thanks to DeRozan’s strong play. Right now, the Heat and the Bulls are the two top teams in the conference.

All is well that ends well, I guess. However, what you cannot take away is the pain both these men felt on that fateful day. These are the types of things that just stick with you forever.