When the playoffs begin in mid-April, the Boston Celtics’ primary focus will soon turn to their pursuit of the coveted Banner 18. But first, the team needs to think through at least one piece of future housekeeping.
On April 1, six months after the deal that brought him from Portland, Jrue Holiday is eligible for an extension. It is clear that both parties want to work together for a long time. Holiday, who will shortly turn 34, was acquired by the Celtics for a high price in October, and he has set himself up for his next big paycheck.
The question is whether the Celtics can afford to be the team that splurges on Holiday given their soaring budget, which will see supermax deals for Jayson Tatum and Jaylen Brown hit the books over the following two summers. It will be challenging for Boston to retain every member of the core of this season for an extended period of time due to a restrictive new collective bargaining agreement.
While building a championship-caliber team, Celtics president of basketball operations Brad Stevens has welcomed contract extensions. However, the team’s current starting five, which has collectively paid over $156 million this season, may eventually exceed $200 million annually.
Before training camp began in October, the Celtics traded away Robert Williams III, Malcolm Brogdon, and a 2024 first-round selection to acquire Holiday. With his great play this season, Holiday is in a good position to opt out and secure a lucrative extension, perhaps lasting up to four years, that might propel him closer to the end of his NBA career. Holiday has a $39.4 million player option for the 2024–25 season.
Some have questioned if Holiday would accept a lower payment to extend his time in Boston by more years. Although Holiday has already accepted sacrifice in Boston, he has effectively increased his market value. Holiday is making 44.5 percent of his shots from beyond the 3-point arc, including a scorching 65.2% from the foul line, a career-high. He will probably make an All-Defense team for the fourth time in a row because he is still an excellent defender. The unimpressive roster of unrestricted free agents expected to enter the market this summer should further guarantee that Holiday’s talents will come at a premium cost.
Stevens acted swiftly to extend Kristaps Porzingis for two seasons at a total of $60 million after acquiring the big man in June of last year. However, the Celtics must be frugal with their spending because Derrick White, their backcourt partner, is also available for an extension and will be approaching the final year of his team-friendly contract next season. Future decisions regarding the composition of this team’s core will need to be made.
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.
Boston may start Payton Pritchard or Hauser, a less expensive option, in the starting lineup in an effort to save money the next season. However, it would be painful to let Holiday go after having to spend a high amount to sign him for the 2023–24 campaign. If Holiday left, there would be trade opportunities to recover value, but that is rarely the best course of action.
