Brad Stevens pushed all the right buttons during his first few seasons as Celtics president of basketball operations. He brought back key familiar faces (Al Horford) and moved on from beloved injury prone ones (Robert Williams, Marcus Smart) before their values dipped en route to putting together a loaded roster that won a title in 2024.
The groundwork was laid out by Danny Ainge nearly a decade ago in drafting Jayson Tatum and Jaylen Brown but Stevens put the necessary supplemental players around the duo. He pushed in the majority of the Celtics’ poker chips in the last two seasons and came out with a title. That part of the planning paid off masterfully.
Stevens and Boston’s front office did put together a fascinating tactic in the midst of planning out their future with a contender. Over the last two years, they decided to pay everyone that matter over the long haul, likely knowing full well the team had no realistic chance of keeping all these pricy long-term deals on Boston’s books beyond the 2024-25 season. Seven of Boston’s eight core rotation players signed long-term extensions between the summer of 2023 and the start of the 2024-25 season.
Some choices were easy (Jayson Tatum and Jaylen Brown supermax contracts). Some were necessary to get a trade done (Kristaps Porzingis). A couple were incredibly savvy (Payton Pritchard and Derrick White’s deals look like bargains a year later).
Ultimately, everyone in the rotation short of 38-year-old Al Horford got paid long-term money. The decision to give out those deals helped to foster a great locker room atmosphere, multiple players told MassLive. No one was gunning for their own stats, since everyone had long-term security.
However, Stevens and the front office have painted themselves into a potential corner beginning this offseason with some of that freewheeling spending. The entire league knows the Celtics need to cut payroll heading into next season. Stevens knew the entire NBA world would see this. Now comes the hard part for the Celtics as the bill comes due for those long-term deals with big raises for Jayson Tatum, Derrick White and Sam Hauser all kicking in this summer.
The premise that Stevens handed out those long-term deals went beyond the positive impact on Boston’s locker room cohesion. The team must have believed all of these deals (short of maybe Jrue Holiday’s) would age well enough over time where moving them would not be an issue, when the time would come. In fact, the bet was that most, if not all of these deals would be able to produce assets for Boston in a trade even if salary trimming was a necessary part of the deal. The thought process?
“Yes, the whole world knows we need to trade one of our core pieces, We will get good bids for them anyway since teams will want those players even with our motives being obvious.”
That thesis is going to be put to a harsh test though following Boston’s stunning second round exit. Holiday’s still a valuable player, but his decline has begun at age 34 and he is still set to make over $104 million over the next three years. Holiday declined a $37 million player option for a lower starting salary ($30 million) this year (which saved Boston tens of millions in luxury tax penalties) but that expensive lengthy deal could be a big obstacle on the trade market.
Porzingis’ deal is set to expire next summer but his value has plummeted in the wake of an injury and illness riddled campaign. It’s tough to imagine Boston getting an asset for getting him off their books at this point. Instead, they may need to sweeten the pot to move him elsewhere.
Ultimately, the extension gamble could still work out. The deals for White and Pritchard will certainly age well and both of those players could be moved for a haul but Boston doesn’t want to do that with either for obvious reasons. Jaylen Brown should fetch a good haul if he becomes available but he’s an All-Star in his prime. Sam Hauser should be attractive to some team needing shooting if he becomes a cost casualty. None of these guys are necessarily the players Boston wants to move now.
Still, the contract for Holiday will be the big test here. The Celtics did not need to give him that extension at that extended length last spring and it ultimately has not aged very well just a year later. Porzingis has not contributed much of anything in Boston’s last two playoff runs due to injury and illness so there will be
All it takes is one compelling offer to emerge for Holiday or Porzingis for the extension gamble to pay off. If not, a more dramatic reset for the franchise could be required in the wake of Jayson Tatum’s injury if moving these big money deals ends up costing Boston valuable assets.