Chris Forsberg

Will the Celtics splurge to extend Jrue Holiday after April 1?

Can the Celtics afford to keep the talented veteran guard past this season?

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The Boston Celtics' singular focus soon will shift to their quest for the elusive Banner 18 when the playoffs arrive in mid-April. But before that, there is at least one bit of future housekeeping the team must ponder.

Six months removed from the trade that delivered him from Portland, Jrue Holiday becomes extension eligible on April 1. Both sides have obvious interest in a long-term partnership. The Celtics paid a hefty price to acquire Holiday in October and the soon-to-be 34-year-old guard has positioned himself for his next big payday.

The question is whether the Celtics, with a ballooning payroll that will see supermax deals for Jaylen Brown and Jayson Tatum hit the books over the next two summers, can afford to be the team that splurges on Holiday. A restrictive new collective bargaining agreement will make it tough for Boston to keep together all the pieces of this season's core deeper into the future.

Celtics president of basketball operations Brad Stevens has embraced extensions while crafting a championship-caliber roster, but the Celtics' current starting five, on the books this season at roughly $156 million in combined salaries, soon could cost in excess of $200 million per year.

The Celtics shipped out Robert Williams III, Malcolm Brogdon, and a 2024 first-round pick to acquire Holiday before the start of training camp in October. Holiday has a $39.4 million player option for the 2024-25 season but, given his strong play this season, is well positioned to opt out and secure a lucrative extension — for as much as four years -- that could take him toward the finish line of his NBA career.

Some have wondered whether Holiday would take a reduced rate to add years to his stay in Boston. Holiday already has embraced sacrifice in Boston but has bolstered his market value with efficiency. Holiday is shooting a career-best 44.5 percent beyond the 3-point arc, including a sizzling 65.2 percent from the corners. He remains an elite defender who seems likely to land on a fourth consecutive All-Defense team. An unspectacular list of unrestricted free agents set to hit the market this summer should further ensure a high price tag for Holiday’s services.

After acquiring Kristaps Porzingis last June, Stevens moved quickly to extend the big man for two seasons at a total of $60 million. But with backcourt mate Derrick White also extension-eligible and entering the final year of his team-friendly deal next season, the Celtics have to be diligent with how they spend. Decisions loom on what exactly the core of this team looks like in the future.

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Any decision — whether it’s to splurge or pivot -- gets a little easier if the Celtics win an NBA title this June. But waiting until the summer to tackle Holiday’s future also leaves open the possibility that he could opt out and explore other options.

That’s somewhat daunting when you consider a contending team like the Philadelphia 76ers will have available cap space this summer. Just think back to 2019, when Al Horford surprisingly elected to opt out of the final year of his deal — albeit after a maddening Celtics season filled with drama and a disappointing finish — to sign with the 76ers. Horford and Holiday share the same agent in Jason Glushon, who also represents the recently extended Brown and the soon-to-be payday-seeking Sam Hauser.

Given the harsh realities of the new CBA, along with potential repeater penalties looming as max-money deals for Tatum and Brown hit the books, the Celtics must decide if it's prudent to pay Holiday and endure the consequences of a bloated payroll, or ponder more immediate avenues to corral spending. The Celtics will trigger repeater penalties next year if they are in the tax for a third consecutive season, or could stiff-arm them a bit by avoiding the tax before Tatum’s supermax hits in the books in 2025-26.

In a quest to drive down costs next year, Boston could elevate a low-cost option like Hauser or the previously-extended Payton Pritchard to the starting lineup. But letting Holiday walk away would sting after paying a steep price to acquire him for the 2023-24 season. There would be trade options to recoup value if Holiday departed, but that’s rarely ideal.

The Celtics have a total salary commitment of roughly $184 million this year, which will deliver a luxury tax bill around $40 million. Even bringing back Holiday at a rate near his player option has the Celtics' roster cost shooting north of $200 million next season, and that’s before potential re-signings of role players like Luke Kornet and Xavier Tillman. Boston would be looking a $300+ million total spend after luxury tax penalties.

Maybe that sort of spend is more palpable than it had been in the past. There is new TV money coming down the road, franchise values are off the charts, and expansion eventually could infuse money that might help ownership justify heavy spends for title-caliber teams.

Holiday has stated, privately and publicly, that he’d like to be in Boston long term. The Celtics have gushed about what he’s brought to the team, particularly in sacrificing some of his individual stats for the betterment of the team this season.

Extensions have helped Stevens keep his team focused on the main goal. It seems unlikely, even if the two sides don’t come to an agreement in early April, that Holiday’s future would be a distraction during the team’s playoff run, but the Celtics are headed towards some tricky decisions sooner than later.

Boston’s front office deserves credit for having the foresight to splurge now in the infancy of the new CBA and constructing a roster that has produced the best record in basketball. This sort of roster might not be sustainable long term, but it’s put Boston in a position to chase Banner 18 before those tougher decisions have to be made.

And those prickly decisions become a little easier to make if a new Larry O’Brien Trophy finds its way to the Auerbach Center this summer.

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