Celtics Face Payroll Crunch as Jrue Holiday Trade Rumors Intensify

The Boston Celtics must make difficult roster choices because their payroll could reach unprecedented heights during the upcoming NBA offseason. The NBA Draft takes place on June 25, 2025, followed by free agency, while the team must handle the strict salary cap regulations of the league. Among the players caught in the rumor mill is veteran guard Jrue Holiday, whose time in Boston may be nearing an end, according to a recent report from Chowder and Champions. The Celtics’ financial strategy is further complicated by broader market trends, such as the potential expansion of North Dakota sports betting, which could influence franchise valuations and revenue streams for high-spending teams like Boston.

The Celtics, coming off a second-round playoff exit in 2025, are projecting a $500 million payroll for the 2025-26 season, including hefty luxury tax penalties. The new collective bargaining agreement’s second-apron restrictions have pushed the president of basketball operations, Brad Stevens, to consider trading high-salary players. Holiday, a two-time NBA champion and six-time All-Defense selection, is a prime candidate with his $34.8 million salary for the upcoming season. His contract, which runs through 2027-28 with a player option, makes him an attractive trade piece for teams seeking a proven veteran.

Holiday’s potential exit stems not from his performance but from Boston’s depth at guard and the rise of younger, cost-effective talent. Payton Pritchard, the reigning Sixth Man of the Year, has solidified his role as a dynamic bench spark, earning $7.2 million next season. Derrick White, younger and on a longer, cheaper contract, outperformed Holiday in most statistical categories last season, making him a more valuable long-term asset. The Celtics’ pre-draft workouts, heavily focused on NBA-ready shooting guards, signal their intent to bolster backcourt depth, potentially at Holiday’s expense.

Trade speculation around Holiday has intensified, with several teams reportedly interested. The Los Angeles Clippers, who bid for Holiday in 2023 when he was traded from Portland, are among the suitors eyeing the 34-year-old guard. A deal could involve players like Bogdan Bogdanovic and Drew Eubanks, though salary-matching rules complicate matters after the new league year begins on July 6. The Dallas Mavericks have also emerged as a possible destination, looking to pair Holiday’s defensive prowess and championship experience with Kyrie Irving and Anthony Davis. NBA insider Marc Stein notes Dallas is exploring “feasible trade pathways” despite the complexities of Holiday’s $104 million contract over three years.

The Celtics’ financial constraints are exacerbated by Jayson Tatum’s Achilles injury, which will likely sideline him for most or all of 2025-26. His $54.1 million salary, part of the richest contract in NBA history, remains on the books, forcing Boston to weigh short-term competitiveness against long-term flexibility. Trading Holiday could help duck under the second apron, unfreezing their 2033 first-round pick and avoiding repeater tax penalties. However, any deal would need to return significant value, with reports suggesting Boston seeks at least a first-round pick.

Other players, like Kristaps Porzingis and Sam Hauser, are also on the trade block. Porzingis, with a $30.7 million expiring contract, has drawn interest from teams like the Phoenix Suns, while Hauser’s $45 million extension and elite three-point shooting make him a cost-cutting target. Boston must balance these moves while preserving the core of Tatum, Jaylen Brown, and White, who are locked in through 2028-29. The team’s interest in the 2025 draft, considered deep and talented, could further shape their strategy.

As the draft approaches, Holiday remains professional amid the uncertainty after Boston’s playoff loss, focusing on preparation over speculation. Whether he stays or goes, the Celtics’ decisions in the coming weeks will shape the franchise’s trajectory for years to come.