The Celtics are trading Jrue Holiday back to Portland for Anfernee Simons and picks, prioritizing payroll flexibility. With stars like Jayson Tatum injured and Porziņģis uncertain, Boston’s future is in flux as new ownership weighs steep tax penalties and roster direction.
After helping the Boston Celtics capture a record-setting 18th NBA championship, Jrue Holiday is heading back to the team that briefly held his rights just a year ago.
Jrue Holiday
Jrue Holiday
Team: Boston Celtics
Position: PG
Age: 35
Height: 193 cm
Weight: 82 kg
Birth place: Los Angeles, United States of America
According to multiple reports, Boston has agreed to trade the veteran guard to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks.
The deal, not yet official, was confirmed by a person familiar with the negotiations who spoke to the Associated Press on condition of anonymity. ESPN first reported the trade details early Tuesday. The move signals a potential shift in direction for a Celtics team that now faces mounting financial pressure, uncertain health, and difficult decisions about its core.
Holiday, 34, played a pivotal role in Boston’s title run after arriving in a trade from Portland last fall—just days after the Blazers initially acquired him from the Milwaukee Bucks in the blockbuster Damian Lillard deal. In his lone season with Boston, Holiday earned his sixth All-Defensive Team selection, bringing veteran poise and defensive tenacity to a loaded starting five.
Yet despite his on-court impact, the Celtics were likely motivated to move Holiday due to the $104.4 million still owed over the next three seasons of the contract extension he signed last year. With Jayson Tatum and Jaylen Brown both on $300+ million deals, Boston’s payroll had ballooned to a projected $225 million, with a staggering $280 million tax bill looming — a combined total that would have shattered NBA financial records.
Holiday’s scoring had dipped to 11.1 points per game, the lowest since his rookie season, though his leadership remained invaluable. Meanwhile, Simons, 25, brings a much-needed offensive boost to Boston’s backcourt after averaging 19.3 points per game last season and 22.6 the year before.
Jrue Holiday
Jrue Holiday
Jrue Holiday
MIN: 30.86
PTS: 10.89 (50.07%)
REB: 4.27
As: 3.87
ST: 1.04
BL: 0.4
TO: 1.33
GM: 70
The Celtics are also managing a series of health setbacks. Tatum, the team’s All-NBA forward, is expected to miss a substantial portion of next season following Achilles surgery. Brown, who signed a five-year, $304 million deal, is coming off knee surgery.
And big man Kristaps Porzingis, due $60 million through 2026, struggled with injuries and illness throughout the playoffs.
The departure of Holiday raises further questions about whether Boston plans to retool or simply shed salary under its new ownership group. A March purchase agreement valued the franchise at over $6.1 billion, but the financial implications of the NBA’s new collective bargaining agreement — including harsh penalties for exceeding both tax aprons — appear to be reshaping how the Celtics manage their championship window.
Before the trade, Boston had already blown past the $155 million luxury tax line, with projections showing it would also exceed the first apron ($196M) and second apron ($208M) thresholds. These higher tiers come with severe roster-building restrictions, including limited trade flexibility and reduced access to free agents.
Team president Brad Stevens, speaking last month after the team’s playoff elimination, acknowledged the challenges of maintaining a contender under the current system. “That’s a good question. I don’t know,” he said when asked if championship windows are shrinking under the cap rules. “Certainly it is more challenging in certain circumstances for sure.”
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