This summer was always going to be an offseason of change for the Boston Celtics. Brad Stevens and Boston’s front office made a strategic push for a title for the last two years, netting the franchise their first championship in over a decade before a disappointing second-round exit in 2025. Even before Jayson Tatum went down with a torn Achilles, moves were inevitable for this group due to Boston’s ballooning payroll. However, Stevens and his staff made an intriguing choice over the last two years while planning for an inevitable change, opting to sign nearly their entire rotation to extensions amid this window of opportunity.
Some of those extensions were no-brainers (Jayson Tatum, Jaylen Brown). Others look like huge steals already (Derrick White, Payton Pritchard) from a value standpoint. The one big one that created some uncertainty involved [Jrue Holiday](https://www.masslive.com/celtics/2025/06/boston-celtics-trade-jrue-holiday-to-blazers-for-anfernee-simons-draft-picks.html). The Celtics gave the 33-year-old four additional years last April despite the very apparent reality they would not be able to afford him (or other key players) beyond the 2024-25 season.
Ultimately, Stevens bet on the value of his players like Holiday holding up even as some aged beyond their primes. That gamble started to pay off on Monday night when the Celtics agreed to send Holiday to the Blazers for [Anfernee Simons](https://www.masslive.com/celtics/2025/06/what-anfernee-simons-brings-to-boston-celtics-after-jrue-holiday-trade.html) and two future second-round picks (2029, 2030).
Holiday’s long-term money scared off some suitors but there was still a market for the 35-year-old veteran known for his defensive versatility and championship pedigree. Sacramento and Dallas were among the suitors for Holiday in recent weeks but the Celtics were able to check off multiple boxes in getting this deal done with Portland. They started the process of trimming payroll (reducing next year’s cap hit by $4.7 million) and also brought in a player whose age timeline (26) could conceivably fit in Boston or with other teams around the league in a subsequent deal.
Simons is earning $27.6 million next year, but without long-term money attached to him, that should make him an easier player to move in a secondary trade, if that’s the path the Celtics want to go. Adding two second-round picks for 2029 and 2030 also doesn’t seem like a big deal for now, but that helps Boston replenish their draft cupboard that had taken a hit amid the Celtics’ all-in push over the next two years.
Stevens’ work this summer is far from done. Boston’s payroll remains $18 million above the second apron and the Celtics could opt to try to cut far more than that since they are still $37 million over the luxury tax line currently, which is especially costly with the Celtics facing stiffer penalties for being a repeater tax team. Trades involving multiple rotation players seems inevitable at this point. The names involved will obviously depend on the strength of the offers.
It’s still not clear what path the Celtics will take to get to more cost savings but the Simons trade was a good first step in that direction, netting Boston assets for a risky gamble on a Holiday extension. rather than letting Holiday walk away for nothing (without an extension).
What road Stevens takes from here is a mystery for now, but the Celtics are well positioned now to continuing retooling for Jayson Tatum’s looming return while bringing their spending back down to a sustainable level.