The Boston Celtics have had a record-breaking regular season, winning 64 out of their 82 games. This outstanding regular season performance ranks as the Celtics’ fourth-best record in franchise history. Boston’s front office deserves a lot of credit for building such a complete roster. However, the future of two key players, Jrue Holiday and Derrick White, remained uncertain until recently.

The past week, the Boston Celtics handed Holiday a four-year contract extension worth $135 million. But Derrick White’s future still remains up in the air. While star players like Jayson Tatum and Jalen Brown have attracted plaudits for Boston’s incredible form, it is Derrick White who has been instrumental in doing the gritty work on defense. Having been traded from the Spurs in Feb 2022, White has averaged career-high 15.2 points, 5.2 assists, and 4.2 rebounds. Therefore, handing him a contract extension may lie as a priority for the Celtics’ front office.

Derrick White is under contract for just one more year before becoming an unrestricted free agent in 2025. However, he will become eligible for a four-year contract extension worth $123 million beginning from 1st July. Celtics’ president Brad Stevens recently provided an encouraging update on White’s contract extension situation. He said, “I can’t talk about much with things that we’re not allowed to discuss until July 1, but Derrick’s had an amazing year. Derrick is a huge, huge part of our team and we want him around for as long as we can keep him around.”

Derrick White has also publicly stated his desire to stay in Boston on several occasions. Before the Celtics’ first game of the 2023-24 season, White said, “I love being here. We got another year after this one.” So if both parties want the same outcome, why hasn’t Derrick White signed a contract extension till now?

Derrick White’s contract could have a significant impact on Boston’s future

The Boston Celtics are currently regarded as one of the best teams in the NBA. However, it has come at a cost. The Celtics have the fifth highest payroll for the 2023-24 season, totalling $183.5 million. Furthermore, they will also be paying $39.1 million in luxury tax bills. But these figures don’t include both Jaylen Brown and Jrue Holiday’s contract extension, which will increase their payroll to approximately $196 million; which could make the Celtics the most expensive team.

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Therefore, it comes as no surprise that the Celtics are taking time to negotiate Derrick White’s contract extension. If they decide to hand White the contract extension, the Celtics payroll for the 2025-26 season would be on pace to cost more than $300 million in tax penalties alone. Few owners will have the appetite to stomach such a high payroll for just one season. However, tax penalties would be the least of the Boston Celtics’ problems. For, they are also on pace to cross the second apron, which will come with its set of repercussions.

Falling over the second apron would greatly affect Boston’s maneuverability to pull off trades, as they will not be allowed to aggregate player salaries. Furthermore, they won’t be allowed to use any preexisting trade exceptions. However, those figures are still more than a season away. If the Celtics manage to win a title during this time period, the ownership wouldn’t mind such a huge luxury tax bill.