The Celtics are going to make notable changes to their roster this offseason and one option they will undoubtedly consider is a Jrue Holiday trade. The 34-year-old veteran was an integral part of the Celtics 2024 championship team and remains a valuable part of the roster. However, his play was up-and-down this postseason amid Boston’s disappointing second round exit to the Knicks.
Holiday has plenty of fans within the organization and around the league, but his age and contract situation makes him a potential candidate to be on the move as Boston tries to retool following Jayson Tatum’s injury and a record-breaking projected payroll for next year. Boston agreed to a four-year extension with Holiday last March that kicked in at the start of this season. Here’s the full contract breakdown:
Jrue Holiday extension
2024-25: $30 million
2025-26: $32.4 million
2026-27: $34.8 million
2027-28: $37.2 million
The challenge now for the Celtics’ brass in today’s CBA is finding a taker for Holiday at those salaries while also allowing Boston to start their own cost-cutting as part of a deal. If Holiday isn’t dealt into open cap space (Brooklyn is currently only team with enough space to absorb his deal), the Celtics would need to take back at least $22.5 million for any trade to work under CBA rules for salary matching.
Which teams could be in the market for the guard despite his high salary? Let’s examine some hypothetical trade partners and possible proposals.
WIN-NOW TEAMS
This would be the preferred path for the Celtics if they elect to trade Holiday since the team wouldn’t have to sweeten the pot for an offer as much. A team would want Holiday the player instead of just serving as a landing spot for a big salary.
With that said, trading away high salaried players is a tough move in today’s CBA environment, and finding a home for a 35-year-old guard removed from his prime won’t necessarily be easy. Holiday could still help teams in the backcourt though and with meager free agent options available, getting Holiday at a reasonable price (from an asset perspective) may be appealing. A few teams to monitor on this front.
Dallas Mavericks
Proposal: Jrue Holiday and draft compensation for Daniel Gafford, Caleb Martin, Jaden Hardy and Olivier-Maxence Prosper
The ultimate-win now team after their disastrous Luka Doncic trade. With Kyrie Irving set to miss a large chunk of next season after tearing his Achilles, backcourt help is needed. Defense also wins championships according to Nico Harrison, so Holiday should be able to help this team on that front as well.
With Cooper Flagg expected to enter the equation as a No. 1 overall pick, Dallas also has some expendable wings on the roster to help with salary matching for Holiday.
How much salary Dallas is willing to add onto their payroll ($192 million) for next season is an open question. There’s no question though that Holiday would help this team’s backcourt right away but they may also pursue less expensive salary options via trade. Due to that, Boston may need to sweeten the pot with an asset/pick.
Likelihood? Considerable if Mavericks like Holiday.
Los Angeles Clippers
Proposal: Jrue Holiday and draft compensation for Bogdan Bogdanovic, Drew Eubanks and Jordan Miller
The Clippers were one of the finalists to trade for Holiday two years ago, multiple sources told MassLive. Boston outbid the Clippers for the guard and now could dangle Holiday as a potential addition to the team’s aging core of Kawhi Leonard and James Harden.
The sell here is easy in theory for Stevens. The Clippers upgrade Bogdanovic with Holiday and look better equipped to maximize whatever Leonard and Harden have in the tank. The long-term Holiday contract could give the Clippers pause though as it extends long past the prime of Leonard and Harden. Can the Celtics do enough to sweeten the pot for the Clippers to absorb it? Or do the Clippers have more appealing options available for taking on more money in a Bogdanovic deal?
Likelihood: Possible, but Ballmer needs to be okay going back into the tax.
Detroit Pistons
Proposal: Jrue Holiday and first round pick for Tobias Harris
While it’s enticing to think of Detroit as a good landing spot for Holiday as a potential mentor for Cade Cunningham, it’s a harder sell from a Detroit perspective. Holiday is not on the right timeline with this core, and his big contract will limit future cap room for younger, better options.
There’s also a cheaper alternative free agent guard option available already in Dennis Schroder. It’s tough to imagine the Pistons jumping on this one unless Boston adds serious sweeteners. That’s something the Celtics would understandably be wary of doing given their limited draft capital. These Pistons have gone all-in on adding veterans lately though successfully (see: last season) so certainly worth the call.
Likelihood: Don’t see it.
Houston Rockets
Proposal: Jrue Holiday and draft compensation for Dillon Brooks and Jock Landale
Ime Udoka would surely love to get his hands on Holiday to improve an already stout Houston defense. Yet, Holiday’s career timeline here doesn’t make a lot of sense here in Houston. He’s a better player than Brooks ($21 million) but is he worth paying $11 million more than him for the next few years? Houston’s offense also needs more help than its defense and Holiday doesn’t provide a ton of help there at this stage of his career.
Likelihood: Not without Celtics sweeteners.
Orlando Magic
Proposal: Kentavious Caldwell-Pope and filler for Jrue Holiday and draft compensation
It’s not hard to see the Magic looking for a Caldwell-Pope upgrade after he shot 26.7 percent from the field in the first round from Boston. However, Orlando’s very young core combined with Holiday’s high salary and age are again a tough match. Similar situation here with the Dillon Brooks hypothetical. Holiday is the better player than Caldwell-Pope ($21 million) but he is $10 million per year better? Probably not when there is so much big money committed elsewhere on this roster already.
Likelihood: Not without more Celtics sweeteners. Orlando also may balk at adding big money to payroll as a third option.
CAP SPACE RENTAL TEAMS
There will be plenty of competition around the league to find landing spots for big contracts. Holiday could eventually land a rebuilding team an asset down the line when his deal gets shorter. For now? The price of taking him on likely comes in the form of draft compensation from Boston. The Celtics would also have to take back a contract or two in salary matching in said scenarios.
This would be a tough spot for Brad Stevens to put Holiday in, just one year after signing him to a big extension. Shipping him away to a non-contender for the next three years would be tough business, but potentially the best way for Boston to recalibrate for the future.
A few potential landing spots to watch for if the Celtics go this route.
Utah Jazz: They were in the mix on Holiday two years ago when the Blazers were hunting for offers. They also have the cap flexibility to take his deal with a couple potential expiring contracts to send back. Boston would need to sweeten the pot though.
Washington Wizards: How would Celtics fans react to trading Holiday with a future first round pick to bring Marcus Smart back (and then probably try to trade Smart afterwards)?
Other teams that have flexibility to absorb big long-term deals for draft compensation: Chicago Bulls, Brooklyn Nets
FINAL THOUGHTS
There are a couple of feasible scenarios on this list (Dallas, LA Clippers) to go along with a few painful ones (see: salary dump trades). For that reason, if Boston can’t find a good fit or the price is too high to move him, there is a chance Boston could hold onto the guard for now. It would be stunning for the veteran guard to finish this contract in Boston for the full remaining three years but the Celtics do have alternative options for moving money that could require less draft capital needing to be sent out the door or a lot more assets coming in (see: Jaylen Brown).
If Boston is committed to the younger parts of their core alongside Tatum (Brown/White/Pritchard), moving Holiday is probably the preferred play if major cost cuts are a priority this summer. Don’t look for the trade winds to stop swirling around him anytime soon in the next few weeks.