It broke just about every Toronto Raptors fan's heart when beloved franchise player DeMar DeRozan was dealt to the San Antonio Spurs in 2018 in a deal that brought superstar and fun guy Kawhi Leonard to Canada.

Of course, much of the pain subsided for fans by the time the Raptors had gone on to win the NBA Finals in 2019, with Leonard awarded Finals MVP.

Leonard's stay in Toronto was short-lived, now the centrepiece of the Los Angeles Clippers, and DeRozan has since left San Antonio to play for the Chicago Bulls. Still, even a few years later, the trade is a constant discussion topic and a source of lingering pain.

DeMar sat down for an interview with Golden State Warriors forward and part-time commentator Draymond Green, discussing his career path and the infamous trade that still weighs heavily.

It's not the first time he's discussed the trade or the Raptors winning a championship without him, but it's definitely the most in-depth he's talked about the topics on record.

DeRozan talks about his culture shock during his first few months attending USC, where he would bounce back and forth between college and his home in Compton to stay grounded. It wouldn't be as easy a few years later, when he was drafted by Toronto 9th overall in 2009.

Draymond Green sets the stage for his career path in Toronto by asking him about draft night all those years ago.

"So, as a kid, essentially, 18, 19 years old, heading into the draft, it's possible you could end up in Michigan. You could end up in Florida, Louisiana. Not only do you end up far away from L.A. You end up in another country," says Green. 

"Take me there. Take me to draft night, getting drafted to Toronto. What's the first thing that goes through your mind?"

DeMar admits he wasn't prepared until the last minute for the possibility of being signed by the lone team outside of the United States.

"I didn't have a passport. I didn't have none of that sh*t. Threw me off. Like, damn, nobody I know has a passport. I got my passport two days before the draft to go to Toronto. I remember going up there by myself that next morning. I'm seeing sh*t in an airport in French. I'm like losing it."

It was just like how he felt in those first months at USC, but the comforts of home were no longer just a 25-minute drive away.

"There go the whole culture shock all over again. And this time around it's somewhere where I can't just go home. I didn't have nobody with me. I was by myself. I remember I was still wearing Chucks in the wintertime. I didn't know how to dress. I'd never been to the cold."

But DeRozan would, as we all know, get very comfortable in Toronto, becoming a cornerstone of the Raptors franchise he helped reinvigorate and a pillar of the community in the process.

The end of the 2017-18 season brought more playoff disappointment at the hands of LeBron James, and while many expected shakeups like the firing of then-coach Dwayne Casey, nobody could have predicted what came next.

Certainly not DeRozan.

He talks about how Raptors GM Masai Ujiri had met with him two days before the trade that shocked the NBA, assuring the star that his time in Toronto was not coming to an end.

"We had a f*cking dinner, you know, have a sit-down and have a conversation about like, all right, we about to do this thing. We're about to give it one more shot, blah, blah, blah. And two days later, you get a call. That was the sh*t that hurt."

"He calls me, so, one, I'm in a movie theatre. To this day, I do not watch this movie — Equalizer 2. My phone keep ringing. It's Masai. I'm like, what the f*ck?. So he texted me and said, 'Deebo, give me a call when you get a chance.'"

"So soon as I send a text back, I get on the 'Gram. I'm like, I don't see nothing on the 'Gram. I'm on Twitter. I'm Googling sh*t. So I'm like, all right. He's just in my mind. So I leave the movie theatre. I get in the car. Call him back. He didn't answer. I'm like, probably ain't nothing. He call me back, asking how was the movie? Like, some casual sh*t, you know what I mean?"

Then Ujiri dropped the bombshell, "We just traded you to San Antonio."

DeRozan immediately asked his driver to pull over, and walked down the street in complete shock.

"I sat outside at a Jack in the Box or Del Taco for like two hours. Swear to god."

"So when it happened, it hit me hard, you know what I mean? It hurt like sh*t because, you know, my whole mindset was like, yo, I'm riding and dying."

"A lot of people always think I was bitter, I was this and all this, like, nah. It f*cked me up because people don't know how much I had put into it. You know, the conversations I had with players, with coaches, the long nights and long days playing through all types of sh*t."

During the Raptors historic Championship-winning run in 2019, DeRozan had to take a break from social media and even left the country during the Finals series, but despite not being part of it, he's happy for his former teammates.

"I'm happy for those guys that won it and everything, but you know, of course, that was my goal was to be the one to make that happen. You know what I mean?"

He was clearly happy for them, and has been spotted with former Raptors teammates on several occasions since being traded.

"We are all expendable at some point, you know what I mean?" he said. "Facts. We only have a short window to do what we do."