The Boston Celtics are trying to thread a tiny needle, keeping together the core of their championship team while selling off the rest of the roster to save money. Should they consider moving off of Derrick White if in return they gain financial flexibility and future assets?
The devastating injury for the Celtics happened in last year's playoffs and determined their offseason strategy. For the Houston Rockets, that injury just happened, as veteran point guard Fred VanVleet tore his ACL and will likely miss the entire season.
The Rockets will go into the season with their current roster and see if their young players are ready to step up, but almost certainly they will need to look to the trade market to replace some of what VanVleet brought: playmaking, on-ball scoring, off-ball spacing, point of attack defense and championship leadership. There are precious few such players in the NBA.
The Boston Celtics have one of them, of course, in Derrick White. He checks all of the boxes, with a bit less on-ball scoring and a bit more versatile defense. White is, in fact, one of the handful of best defensive guards in the league, which is all the more impressive given that guard defense tends to be a young man's game.
Yet White is also 31 years old, and while the Celtics and their fans may hope this descent into restructuring the roster is a one-year blip, the reality is that the Celtics will likely need another year or two to get back into the ranks of contention. And by that point, White will be 33 or 34 and very much aging out of his prime.
White's value will never be higher; if the Rockets come to the Celtics with a massive offer, should Boston consider? Let's take a look at this trade pitched on Space City Scoop and see if it would make sense for the Celtics to accept.
The Rockets could trade for Derrick White
Because the Celtics are trying to get out of the luxury tax, any trade for White will need to include financial savings. At the same time, the Rockets are hard-capped at the first tax apron and perilously close right now, so they need to reduce their salary as well. That requires adding in a third team, the Brooklyn Nets, who can take on the contract of Fred VanVleet in this deal.
Here is what such a trade could look like:
The Rockets add Derrick White to propel them back into the ranks of contention while saving a few million to open up breathing room under the first apron. The Brooklyn Nets take on a large chunk of salary for this season in exchange for a first-round pick, and if VanVleet opts into his contract for next season suddenly they have a valuable asset to flip next summer.
What about the Celtics? This deal leans into the "gap year" idea for the Celtics, as the only win-now piece they would get back is two-way forward Haywood Highsmith. But in return they get a trifecta of valuable assets that can form a foundation for building the next great Celtics team.
Reed Sheppard was at the top of many draft boards heading into the 2024 NBA Draft, a high-volume shooter and playmaker. The Celtics love high-volume shooters, although Sheppard's defensive chops are not up to Boston level. He could develop into a starter with the Celtics, or he can bomb away this year and be at the centerpiece of a trade package for a star down the line.
Boston also picks up two picks, one of which is the better of Houston and Brooklyn's first-round picks in 2027. The Rockets project to be quite good in 2027, but the Nets are likely to still be quite bad. The Celtics have certainly reaped the rewards of owning Brooklyn pick swaps in the past; could they once again land a top pick to add to their core of Jayson Tatum and Jaylen Brown?
Finally, the Celtics also save around $12 million in this deal, dropping them out of the luxury tax entirely. This allows them to move on from Anfernee Simons in a trade that brings back value, not merely saves them money. It sets them up financially to build the team back into contention in the next few years by resetting the luxury tax clock.
Is that enough to trade Derrick White? Perhaps not; he is beloved in Boston and the perfect star-level role player for a contender. Yet his value will never be higher, and this trade brings back legitimate assets for the future.
Should the Celtics consider this midseason trade? Yeah, they at least need to think long and hard about it.