Jrue Holiday agreed to a four-year, $135 million extension on Wednesday, according to Adrian Wojnarowski, erasing any chance he reaches free agency this summer. The deal potentially keeps him in Boston through the 2027-28 season, with that final year a player option, according to Adam Himmelsbach.
Here are some takeaways without knowing all the fine contract details yet.
- Holiday reportedly declined his $37.4-million player option as part of the extension and will instead make roughly $30.1 next season, serious luxury tax savings for the Celtics as Jaylen Brown begins his super max extension. That’s the biggest win for Boston beyond keeping Holiday in town long-term, with Brian Robb calculating $35-million in savings including luxury tax while Bobby Marks predicted that Boston could sneak below the second tax apron next season if necessary.
- Holiday’s big wins: $35-million in 2027 at age 36 and $37.4-million at 37. He joined Steph Curry, Al Horford and LeBron James among the richest contracts signed this late into an NBA career.
- The role adjustment Holiday already underwent prepares him to acclimate more successfully into success later into his career. This extension probably looks worse in Milwaukee, where they often depended on him as a No. 2 option on offense. He’s taking 5.3 fewer shots per night in Boston and shooting 43.1% from three, including the best corner mark in the league (61.1% on 90 att.). He’s also quarterbacking the defense.
- Signing Holiday to a contract like this felt inevitable in adding him in September. That trade created a six month breathing period until he became extension-eligible again on Apr. 1. The deal came together between Boston and Holiday agent Jason Glushon, the architect of the most recent Jaylen Brown and Al Horford contracts. He also represented Marcus Smart and will soon search for Sam Hauser’s first big pay day over the next year.
- The $135-million number doesn’t look as bad next to $221-million, the max extension Holiday could’ve signed starting at $51-million. He couldn’t find that in free agency, but some teams like Detroit, Oklahoma City and Philadelphia could’ve stressed Boston entering a second apron environment where finding a Holiday replacement would’ve been next to impossible. The two sides could’ve played out the year on his player option, but that was probably less enticing to Holiday after sacrificing so much at 33.
- This deal almost certainly won’t age well by 2027-2028. That’s the cost of guaranteeing the highest possible chance of winning now, like giving up the 2028 draft pick swap to the Spurs in the Derrick White deal and sending two firsts to the Trail Blazers for Holiday in the first place, alongside Malcolm Brogdon and Robert Williams III to fulfill Portland’s value of four first round picks on the star guard. They loved Holiday and it’s paid off immensely in year one.
- The books for 2024-25 now: Brown $49.4M, Tatum $34.8M, Holiday $30.1M, Porzingis $29.3M, White $20.0M, Horford $9.5M, Pritchard $6.7M, Springer $4.0M, Brissett $2.5M (player option), Walsh $1.9M, Queta $2.2M (projected non-guaranteed), Hauser $2.0M, along with first and second-round picks. Marks calculated that as falling $6-7 million over the second apron. That means a frozen draft pick, no mid-level exception, no aggregating salaries in trades and other penalties like not being able to buy expensive buyout players. Repeater tax payments loom in the later stages of Holiday’s deal too, but they have some time prior.
- The question on everyone’s mind: how does this impact Derrick White? Jayson Tatum will inevitably sign his super max extension, that’ll begin in 2025-26, this summer. White appears less likely to sign on long-term, limited by his relatively lower finishing salary to close this deal. He can only extend for starting at 140% of $20-million, roughly $27-million, with 8% raises that would amount to just over $120-million over four years. That’s not enough in today’s cap environment for an all-defensive starting point guard who’s shooting just south of 40% from three, but that restriction lifts in free agency. The Celtics showed some pause in extending him two years before he reaches that point, so now he’ll likely reach the open market in 2025. Boston maintains Bird Rights and the ability to pay him up to his max then. Holiday doesn’t change that in the near term, his short term pay cut could actually help, but his salary being larger and on the books later could become a consideration as the team charts its 2027-28 finances. A distant consideration as this deal shows, however. White turns 30 next season and would begin his next contract at 31.
