Dec 7, 2025; Toronto, Ontario, CAN; Boston Celtics forward Jaylen Brown (7) controls the ball against Toronto Raptors guard Scottie Barnes (4) during the second half at Scotiabank Arena. Mandatory Credit: John E. Sokolowski-Imagn Images
Major Splash: Jaylen Brown, Boston Celtics

Raptors receive: Jaylen Brown

Celtics receive: RJ Barrett, Jakob Poeltl, Ochai Agbaji, 2027 first-round pick, 2029 first-round pick, 2031 first-round pick (top-10 protected)

In this scenario, the Raptors trade RJ Barrett, Jakob Poeltl, Ochai Agbaji and three first-round picks to the Boston Celtics for Jaylen Brown. On the surface, that may seem like too steep of a price. Yet, the soon-to-be five-time All-Star has proven he has what it takes to be a No. 1 option for a playoff team. As arguably the most dominant two-way player in the league, he’d bring the best of Barrett’s offense, the best of Agbaji’s defense, and more. In essence, he’ll elevate Toronto’s play at both ends of the floor at a time when they want to take a step up as a franchise.

To be clear, there’s no indication that the Celtics want to trade Brown or that he’s available. Even so, the right offer could be too difficult to pass up. With this package, Boston would acquire three starters (one of whom routinely displays borderline All-Star talent) and three first-round picks. If Jayson Tatum’s injury proves to be career-altering, this could be the type of deal that helps them navigate their next era.