On Wednesday, Jrue Holiday secured a four-year extension worth $135 million, as reported by Adrian Wojnarowski, eliminating any possibility of him entering free agency this summer. According to Adam Himmelsbach, this agreement could keep him with Boston until the 2027-28 season, including a player option for the final year.

Key points from the agreement include:

Holiday opted out of his $37.4 million player option for the upcoming season, choosing to earn about $30.1 million instead. This move provides the Celtics significant savings under the luxury tax, particularly valuable as Jaylen Brown starts his super max extension. Estimates suggest Boston could save around $35 million, including luxury tax savings, with Bobby Marks indicating the possibility of the Celtics falling below the second tax threshold next season if needed.

Holiday’s financial highlights include earning $35 million at age 36 and $37.4 million at age 37, joining the ranks of Steph Curry, Al Horford, and LeBron James in securing one of the most lucrative contracts later in an NBA career.

Holiday’s adaptation to a changed role in Boston, compared to his time in Milwaukee where he was a primary offensive option, sets him up for success in the later stages of his career. His efficiency has improved in Boston, where he’s taking fewer shots but making a higher percentage from the three-point line, leading the league in corner three-point percentage.

The extension, negotiated between Boston and Holiday’s agent, Jrue Holiday Secures $135 Million Extension with Celtics, Influencing Team’s Financial Strategy and Future Composition

was anticipated since his trade to the Celtics. Glushon, who has a history of securing significant contracts for players like Jaylen Brown and Al Horford, played a key role in this deal.

While Holiday’s $135 million extension might seem substantial, it’s relatively modest compared to the maximum $221 million extension he could have pursued. This decision reflects a strategic compromise to ensure Boston’s competitive position, given the difficulties in replacing Holiday and maintaining financial flexibility under the salary cap.

Critics argue the deal might not favor Boston by its end in 2027-28, citing the sacrifices made, including draft picks, to secure Holiday. Nonetheless, this move underscores Boston’s commitment to winning now.

Looking ahead to the 2024-25 season, Boston’s salary commitments include significant figures for Brown, Tatum, Holiday, Porzingis, and others, placing the team just under the luxury tax threshold. This financial strategy limits their flexibility in trades and acquiring players but is a calculated risk to maintain a competitive roster.

One significant question is how this deal affects Derrick White’s future with the team, especially considering Jayson Tatum’s upcoming super max extension. White’s potential extension is limited by salary cap rules, making his long-term future with the Celtics uncertain. However, Boston retains the right to offer him a competitive deal when he reaches free agency.

In summary, Holiday’s extension reflects Boston’s strategic financial management and commitment to maintaining a competitive core, with considerations for future financial implications and team composition.

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