#5: DeMar DeRozan
During his three years in San Antonio, DeMar DeRozan put up big numbers but wanted to play in a bigger market after his play was largely ignored. The grass isn't always greener, however. While the Chicago Bulls had a strong season during DeRozan's first year with the team, they missed the playoffs last season.
Chicago could decide to run it back, but he will be a free agent after next season. If they again fail to live up to expectations, the Bulls might trade him before next summer, when he will be nearly 35 years old. His first choice in free agency might not be his former team, but he was a Spur when they were just trying to remain competitive post-Kawhi Leonard. Now, they look much more appealing as an option, perhaps even more so in the summer of 2024.
Although there is a way to envision DeRozan giving the Spurs a look in free agency, there would need to be mutual interest. Even though he didn't burn bridges by leaving, there was a reason why the team failed to win much during his tenure: he's a highly skilled scorer and passer, but he needs the ball in his hands to be effective, and he isn't a good defender. Neither of those things make him a good fit now, let alone in a year. Never say never, but a reunion probably isn't going to happen.