The agent told The Athletic that DeRozan, who can utilize a player option in his contract to end his time with the Spurs, and former Toronto Raptors teammate Fred VanVleet may sign with the Detroit Pistons to reunite with head coach Dwane Casey.
"DeMar doesn't like San Antonio and doesn't want to be there," the agent said. "If those guys leave, they land with Dwane Casey in Detroit. That relationship with the former coach is strong. Comes down to money [for VanVleet] and the situation in Toronto is rough with the taxes. VanVleet on the Pistons elevates his status as the No. 1-2 guy on a team."
DeRozan was traded from the Raptors to the Spurs in July 2018 as part of a blockbuster deal that sent Kawhi Leonard to Toronto. It was a stunning move after the USC product spent the first decade of his career with the franchise and built a strong friendship with backcourt mate Kyle Lowry.
Casey, who'd been fired by the Raptors two months earlier, was quickly hired by the Pistons.
That offseason's overhaul resulted in Toronto capturing its first NBA championship in 2019 with Leonard being named the Finals MVP.
The move that made the title possible shocked the longtime face of the franchise, though. He told ESPN's Chris Haynes in the aftermath of the trade it caught him off guard because previous discussions with the front office led him to believe he wasn't getting moved:
"Man, I was really stuck. I couldn't think for a second because it just didn't feel real. I didn't have no indication like it would be something else. If I knew that, I wouldn't have reacted the way I did. I would have been prepared for it. But it caught me completely off-guard because I'm thinking this is another summer. Move forward. I talked to my teammates every single day how we can get better. So to hit me with that at midnight out the blue, like, c'mon. Two days prior, it was asked, 'Is anything going on?' If it is, just let me know because the rumors keep coming up. Two days later, you're going here."
DeRozan has continued to produce at a high level in San Antonio. He averaged 22.1 points, which ranked 18th in the NBA, 5.6 assists and 5.5 rebounds in 68 games during the 2019-20 season.
The Spurs had restructured their offense to fit the mid-range strengths of the 31-year-old California native and power forward LaMarcus Aldridge, which was a unique change at a time when most teams are revolving their offensive game plan around the three-point shot.
Now, with the team's playoff streak ending after 22 years, a partial rebuild may take place, which could include the departures of both DeRozan and Aldridge, who has one year left on his contract.
Portland Trail Blazers guard Damian Lillard mentioned Aldridge as the former teammate he'd most like to see return in an April Q&A session. The post was later deleted.
It sets the stage for a potentially roster-altering offseason in San Antonio, and perhaps reunions in both Detroit and Portland in the months ahead.