Jrue Holiday enters the 2025 offseason as the most widely reported Celtic who could move this offseason in an effort to dodge the second apron. His age, slightly diminished productivity in 2024-25 and the clear value he could provide to ascending or contending teams all make it plausible he could become the one to go. Holiday exited the season after a solid playoff run, albeit one limited by a hamstring injury, hopeful that the Celtics can continue to contend for championships and hopeful he’ll be part of it.
He signed an extension in 2024 that carries through a player option in 2028 worth three-years, $104.4 million.
“I think we still have a really, really great opportunity, and a great window to be successful and win a championship again,” Holiday said last week. “I think the talent that we have, not only on the court, but the coaching staff, all the way up to Brad has been amazing. The opportunity to win is now and I still want to be part of it.”
Jake Fischer reported that Boston might have to attach draft capital to Holiday due to the long-term nature of his contract. The length of the deal did feel bold at the time, beginning in his age-34 season where he had a $37.3 million player option. It’s possible the Celtics knew he would decline it and explore free agency. It’s also feasible that the team wanted to reap the benefits of reducing his salary to $30 million for immediate tax benefits in exchange for guaranteed money later. Holiday benefited from that for obvious reasons. Boston allowed itself to run back a championship roster and have control over his future, whether they wanted to trade him or retain him.
Yet one thing that became evident since the new CBA began is the power of an expiring contract. The Clippers let Paul George go and utilized those savings on quality role players. Sign-and-trades along with recovering draft assets while moving on from guaranteed long-term money like Holiday’s could prove more rare this decade.
Holiday’s salaries aren’t exorbitant as a percentage of the cap. He’ll make roughly 20% of the NBA salary cap over the next three seasons. Other players who make that percentage now include Devin Vassell, Jerami Grant, Nic Claxton, Miles Bridges, John Collins and Andrew Wiggins. Considering his defensive skill set, his impact doesn’t fall far below those players, but it’s not clear who he’ll be at 37 after an injury-filled year.
That’ll inevitably limit the number of teams interested in him this season, along with other rivals potentially becoming interested in downsizing their payroll. Other contenders might look to stars like Giannis Antetokounmpo before considering a Holiday-level addition. The Celtics will need to exercise some patience.
There are some suitors who make sense, and even some trades where Boston could avoid sending out draft compensation. As we wrote here previously, the Celtics don’t have the maximum flexibility with their future first round picks, so they’ll need to exercise some caution in when they deal them and for what. Boston doesn’t need to dive below the apron and luxury tax lines until the trade deadline, but the best opportunities for moving money come in the offseason.
They also won’t have much control over which opportunities emerge around the league. The Brooklyn Nets’ cap space will prove necessary to offload the greatest percentage of any contract the Celtics send out by re-routing money elsewhere.
Holiday remains a valuable player in Boston for winning and stability’s sake. They could carry any player, including him, into the season to assess this group’s chance of competing before deciding on their future later.
If they make the call, organizationally, to take a step back, here are some possible trades that could emerge.
Dallas Mavericks
This is the most likely Holiday trade if other teams (the Nets) are willing to absorb Daniel Gafford and PJ Washington. The Mavericks would take on Holiday’s long-term money into a salary slot where they could potentially save money through Gafford and Washington’s expiring contracts. So Boston would probably compensate the third team in this case.
How much? It would depend on whether Dallas moves on from Caleb Martin, who’s owed three-years, $29 million, or smaller salaries like Olivier-Maxence Prosper ($3M), Jaden Hardy ($6M) and Dwight Powell ($4M player option). Since the Mavs save money in that trade too, they could potentially help incentivize the Nets to do it.
That’s only if they value Holiday’s ability to sustain the team through Kyrie Irving’s absence, which will continue through at least January. Dallas might find better ways to utilize its surplus at forward and center, but their need for guard help with only Klay Thompson, Brandon Williams and Hardy signed at guard. Dante Exum is a free agent.
Note as well, for cap purposes, that No. 1 overall pick Cooper Flagg will make $13.8-million next year. That means if they hard-cap themselves at the second apron by trading for Holiday, they need to stay far below the second apron line. That could force them to trade more, rather than fewer players in this deal, and raises the question of whether it’s worth shedding depth for Holiday. I’d consider this deal possible, but improbable.
Orlando Magic
This trade feels more plausible. The Magic need shooting and a veteran presence, and Holiday doesn’t compromise their defense. He could even start next to Jalen Suggs and create a ferocious back court. The Celtics help offset some financial concerns in this deal by bringing back Kentavious Caldwell-Pope, a risk ahead of his age-33 season, but his salary declines to $21.6 million for the next two seasons, far below Holiday’s number. He also provides some comparable skills, though his shooting fell to 34.2% from deep after back-to-back 40% seasons in Denver. Gary Harris Jr. would join him as a capable depth player and expiring contract that the Celtics could move later. Ideally, Orlando could re-route the other outgoing salaries, perhaps Goga Bitadze and Jett Howard’s deals, elsewhere. Injured Moe Wagner ($11M) could also move. Calling the Nets.
LA Clippers
The Clippers have some middle-tier salary players, including Bogdan Bogdanović and Derrick Jones Jr., and Drew Eubanks. Those three players combine for enough salary to match Holiday, a player they had interest in two years ago. Boston wouldn’t save a ton of money even while re-routing Eubanks elsewhere. Bogdanović would be more difficult to trade on a two-year deal, Atlanta had to attach draft picks when they sent him to LA, but Jones Jr. would probably draw interest now or later. This would be the kind of trade where the Celtics reduce their payroll in several steps over time. If Boston brought back all the salaries, they might avoid sending out picks.
Charlotte Hornets
The Hornets have expiring salary players who could save the Celtics money immediately and after next season if they can’t trade them later in the season. Is Charlotte ready to make a veteran addition? Charles Lee’s presence as a former Holiday coach between Milwaukee and Boston makes it worth watching. The Hornets have almost $45-million in space below the first apron, so they’re a potential destination for Holiday and Sam Hauser.
The Giannis trade
If no teams want Holiday outright to begin the summer, maybe the Celtics get involved in one of the offseason’s larger trades like a potential Giannis Antetokounmpo one. If the Spurs need to offload Devin Vassell, Keldon Johnson, Jeremy Sochan and others while acquiring Antetokounmpo, they could opt to add multiple rotation players or one larger starting level talent in addition to their new star. Splurging on Holiday would limit the Spurs’ depth, as they’d become hard-capped and only have just short of $60-million in space below the second apron after bringing in Holiday and Antetokounmpo, whose chemistry is obvious. San Antonio would need to trade six players to make the money work, and Milwaukee probably won’t want to acquire all of them.
If the Celtics help facilitate the trade while getting below the second apron, perhaps by enticing Brooklyn with draft capital, it would allow them to include Hauser in the money-shuffling. Deals that don’t finish with the Celtics below the second apron can’t involve multiple Boston players going out. The Celtics save roughly $23 million and can slide below the apron with this and another move like declining JD Davison’s team option.
Conclusion: There are multiple reasons for the Celtics could explore trading Holiday, from him playing on a long-term deal to avoiding the risk of injury or further decline into this season, along with the benefits of Payton Pritchard knowing he would start to begin next year. It could also jump start the process of moving the players who come back in a Holiday deal if Boston doesn’t see them as long-term parts of the team or wants to further reduce salary. That process will probably happen in several steps due to the nature of the CBA, and once the Celtics get below the second apron, they have more flexibility to do different types of trades.
I do not picture Holiday entering training camp with the team, but they shouldn’t rush or force a trade just to do it. There are too many teams that would still want one of the highest-regarded competitors in the league if he’s still playing at that level. Remember, the Celtics don’t need to dodge the apron until the deadline.