The Celtics started their work early ahead of Thursday’s trade deadline with the acquisition of Xavier Tillman on Wednesday. The big man helps shore up the team’s depth up front while also leaving open plenty of doors for Boston to make subsequent moves on Thursday in the hours leading up to the trade deadline.
With Lamar Stevens heading out the door in the deal and Brad Stevens openly talking about his hopes of landing a wing last month, there’s still an opportunity for Boston to take another swing on Thursday on adding to the roster.
While there are plenty of names that could help provide some more depth for Boston’s bench at a reasonable cost on the wing (Otto Porter Jr. Delon Wright, Saddiq Bey, Jordan Nwora, Naji Marshall, John Konchar, Torrey Craig, Kris Dunn), there is a notable name that’s still worth wondering about.
The Celtics have the assets to take a big swing at Alex Caruso and make the Bulls listen. A closer look at what a serious offer would look like and whether it’s a realistic possibility.
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Salary matching for potential trade
Caruso is in the third year of a four-year contract with the Bulls, earning $9.4 million this season. That number would be too big to fit into the Grant Williams TPE for the Celtics but the team could maneuver some players on the bench to make the money work without touching their top six players.
Boston would need to send out at least $8.6 million to fall within salary-matching parameters for a second apron team. Boston could do that by cobbling together some salary at the back end of their roster along with a key guard.
Payton Pritchard ($4 million) would get the Celtics almost halfway there. From there, three more players would need to be included to get to the $8.8 million. Assuming Sam Hauser and Luke Kornet are off limits in this deal, that means a combination of Oshae Brissett, Dalano Banton, Svi Mykhailiuk and Jordan Walsh would need to head out the door to reach that $8.8 million.
Now any 4-for-1 trade would be tough to pull off for roster space reasons but the Celtics would be able to use the Grant Williams TPE in this scenario if they wanted to take back some talent. Chicago could send back multiple players that fit into the TPE to eliminate the need for the Bulls to waive or trade away other players simply to create roster space.
The Bulls have a few of cheaper players that could fit in this type of scenario such as Torrey Craig ($2.5 million) or Terry Taylor ($2 million). Craig could end up being useful depth on the wing as well for Boston in said scenario.
How many draft picks should Celtics be willing to offer?
With the salary matching workable in theory, the bigger question for Stevens and the Celtics front office is how hard to push on the draft compensation front in a potential offer. Multiple reports out of Chicago have signaled that the Bulls are content to keep Caruso unless they are ‘bowled over’ in a deal.
The inclusion of Pritchard in any offer would change the dynamics somewhat for Boston on draft compensation. He’s well-liked within the organization and is under a very reasonable contract long term that should hold some value (perhaps slight) around the league. Would the Bulls insist on two future first-round picks in addition to Pritchard for Caruso? Or could the Celtics sell the prospect of multiple second-round picks along with the first-round pick to the Bulls due to Pritchard’s value? The latter scenario feels unlikely with Chicago’s reported insistence on staying competitive and making a run at the play-in tournament.
The dynamics of offering two first-round picks would be complicated for Boston and limiting for the future. How lightly protected would they be willing to make them? How far out would they be willing to trade them to entice the Bulls? Would some additional sweetener be required with second-round picks? How far the Celtics would be willing to go here makes all the difference but it’s a path that should be considered. A 2024 first round pick and a lightly protected future first round pick (beyond 2026) should gain Chicago’s attention.
Insurance for Jrue Holiday’s future?
The veteran guard is on an expiring contract with Boston and spoke to MassLive last month about his desire to stay in Boston long-term. While the Celtics would certainly like to retain the former All-Star, the challenge will be fitting him into the budget. Boston will need to make tough choices by the summer of 2025 about which starters they would like to retain if they plan on keeping Jayson Tatum and Jaylen Brown together while their super-max contracts kick in.
The odds of Boston being able to keep Holiday and White both around that point on new deals seem remote. Acquiring Caruso this year would not only increase Boston’s title odds in theory this season but could also protect against the possibility that Holiday’s salary demands are a bit too high for Boston’s tastes. Caruso is also earning a modest $9.5 million so throwing a bevy at draft picks is easier to swallow from that standpoint. If Holiday stays, the Celtics have a phenomenal top-7 players in their rotation for the next 1.5 years. If they lose Holiday, having Caruso around at least provides an acceptable replacement for one year.
Final thoughts
All of these considerations won’t mean much if the Bulls don’t have a semi-reasonable asking price for Caruso. Anything beyond two first-round picks and Pritchard is something Boston will understandably walk away from (and there’s a case to be made for the front office to not even stretch that for). However, during a season in which Boston has pushed a lot of their chips in with the acquisition of Holiday back in September, Caruso is a playoff proven performer who would be a notable upgrade over Pritchard. Given the level of competition waiting in the later rounds of the postseason for this group, that type of boost could be warranted.
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