After a disappointing playoff exit and compounded by star Jayson Tatum‘s season-ending Achilles injury, the Boston Celtics have stunned fans by trading two-time NBA champion Jrue Holiday to the Portland Trail Blazers.
In return, they secured sharpshooter Anfernee Simons and two future second-round picks. Here’s a full breakdown of why this trade makes sense for both parties, and what it signals for Boston’s future.
The driving force behind the trade lies in the Celtics‘ precarious salary structure. With Tatum sidelined and plans to pursue deeper playoff runs, Boston risked slipping into the dreaded “second apron” of the luxury tax, triggering severe financial penalties.
Holiday‘s massive upcoming salaries ($32.4 M in 2025-26 and increasing thereafter) were a key concern.
By sending Holiday‘s contract to Portland, Boston saves approximately $40 million in luxury tax exposure. As Reuters outlines, Holiday is midcontract on a $134.4 million deal, making the divestment essential to avoiding crippling tax bills.
NBC Sports Boston confirms Dallas even explored Holiday as cost-cutting leverage, though acquiring his contract posed complications. ESPN’s Bobby Marks emphasized the need to trim nearly $20 million to leave that second apron threshold intact.
Performance decline and long-term planning
Beyond dollars and cents, Boston also assessed Holiday‘s on-court value. At 35, he posted just 11.1 points, 3.9 assists, and 4.3 rebounds last season-his lowest scoring output since his rookie campaign.
His 35.3% three-point shooting also marked a decline from prior years.
Still, his defensive mastery and championship pedigree remain attractive. As The Athletic’s Jay King noted, despite sliding shot efficiency, Holiday‘s leadership and kill-court reputation make him valuable for contenders.
The trade assets: Simons and future picks
In return, Boston acquired All-Star guard Anfernee Simons, plus two second-round selections. At 26, Simons aligns seamlessly with Joe Mazzulla’s three-point-focused offense, averaging 19-20 points and hitting nearly 38% from deep last season.
Moreover, Simons is on an expiring contract, offering Boston short-term firing power with none of the long-term salary commitments tied to Holiday.
With Jayson Tatum out and a potential overhaul looming, front office movement seems inevitable.
NBA insider Jake Fischer reports that Boston may need to trade Kristaps Porziis or Sam Hauser as well to balance finances.
Leadership inefficiency under a rich payroll was noted by former co-owner Wyc Grousbeck: “It’s not the luxury tax bill, it’s the basketball penalties,” he said of the second-apron constraints.
Read the full article here
