8. Gary Trent Jr.
Tatum left Duke to enter the 2017 NBA Draft with Trent Jr. replacing him for the Blue Devils. Duke made the Elite Eight in 2018 with Marvin Bagley III, Wendell Carter Jr., and Grayson Allen playing alongside Trent Jr. The former Blue Devils certainly have a connection and plenty to bond over.
Trent Jr. has an $18.5 million player option for next season that he is expected to decline to become an unrestricted free agent. The six-foot-five wing has averaged 17.7 points and 1.6 steals since joining the Raptors in 2021. With the entire league searching for wing depth, Trent Jr. is likely to cash in on a massive payday.
Would he have interest in taking a pay cut to join Jayson Tatum in Boston? That seems extremely unlikely, so the Celtics would have to pull off a sign-and-trade for the 24-year-old. Would Boston be willing to give up Malcolm Brogdon or Derrick White to get Trent Jr. from Toronto?
The Raptors are facing an uncertain offseason. They will have a new coach and are likely to shake up their roster after missing the playoffs for the second time in three years. Could Gary Trent Jr. be playing for a different team next season? Do not rule it out, but the Boston Celtics seem to be an unlikely option.