A little over a year ago, the Boston Celtics were flying high. They were coming off their 18th championship in dominating fashion, gentlemen sweeping Luka Doncic and the Dallas Mavericks. But things move fast in the NBA, and after a second-round exit to the New York Knicks in the Eastern Conference playoffs, they are taking a massive turn to better prepare themselves for the future.
With Jayson Tatum feared to miss most of the 2025-26 season with a torn Achilles, Boston is pivoting to a soft rebuild, evident by their moves this offseason of trading key pieces from their championship team. They offloaded Jrue Holiday to the Portland Trail Blazers and Kristaps Porzingis to the Atlanta Hawks in what were salary dump trades.
President of Basketball Operations Brad Stevens always seems to have something up his sleeve, and there could still be moves to be made, including guard Derrick White.
Derrick White Shipped up North to Toronto in a Trade Idea
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It feels disingenuous to call White a role player because of how important he has been to the Celtics since he arrived from the San Antonio Spurs in 2022. In his postseason career with Boston, he's averaged 13.3 points per game, shooting 39% from deep while also playing stellar defense. But his four-year $118 million extension may be too much for the Celtics to carry while they enter a gap year without their MVP-candidate Tatum.
Enter the Toronto Raptors, who themselves have been undergoing a rebuild but look to finally break through this season after acquiring former All-Star Brandon Ingram from the New Orleans Pelicans at last year's trade deadline. White could be the perfect complementary piece to a Raptors team with a lot of young, unproven talent.
Dave Holcomb of Sports Illustrated [proposed](https://www.si.com/onsi/fantasy/nba/derrick-white-nba-mock-trade-boston-celtics-toronto-raptors-rumors-news) the deal:
Boston Celtics receive: Gradey Dick, three first-round picks, and a future conditional pick swap
Toronto Raptors receive: Derrick White
"The Celtics are set to regress even with White on the roster in 2025-26." Wrote Holcomb. "If they traded him for multiple first-round picks, Boston could accelerate any potential rebuild that may be looming for the franchise."
While the Celtics are giving up the best player in the deal, they're getting back a bevy of draft capital that they can use in the future to move up in the 2026 NBA Draft or go all-in on acquiring a new star player once Tatum returns from injury.
"The Celtics don't have to eventually use every selection in the draft. They could repackage them for players once it's confirmed Tatum is back healthy and ready to make Boston competitive again."
It remains to be seen if Boston plans on moving off White, but if they were to, they would get quite the haul in return and set themselves up well for the future. Who knows? Maybe a certain superstar out of Milwaukee will request a trade this upcoming season, and the Celtics will be ready with draft picks hand over fist.