The Boston Celtics officially kicked off their offseason maneuvering with a major move on June 23, 2025, by trading Jrue Holiday to the Portland Trail Blazers. In exchange, Boston acquired scoring guard Anfernee Simons and two future second-round draft picks. The deal, confirmed by multiple league sources, is more than just a roster reshuffle—it’s the first domino in a broader salary cap strategy.

Brad Stevens, the Celtics’ president of basketball operations, is expected to remain active in the trade market as Boston attempts to clean up a ballooning payroll and get under the second luxury tax apron.

Jrue Holiday, 35, is still widely considered one of the NBA’s top perimeter defenders and a proven postseason contributor. But with three years and $104.4 million remaining on his deal—including a player option for the 2027-28 season—Holiday became an obvious candidate for salary-related movement.

By trading Holiday, the Celtics have saved approximately $4.7 million in salary for the upcoming 2025-26 season and cleared $72 million in future salary commitments from the books. Boston’s ownership group and front office have been transparent about their desire to duck under the league’s restrictive second apron, and this trade is a tangible step in that direction.

Despite the move, Boston remains about $18 million over the second apron. League insiders expect further transactions as Stevens attempts to create flexibility. According to ESPN’s Bobby Marks, this trade is “just the start” of what could be a transformative offseason in Boston.

While Jrue Holiday played an integral role in helping the Celtics capture the 2024 NBA championship, his performance took a noticeable dip during the 2024-25 season. His scoring average dropped, his assist numbers declined, and his three-point shooting regressed from 42.9% to 35.3%.

In the 2025 postseason, Holiday averaged just 9.5 points per game, and a nagging hamstring injury sidelined him for the final three games of Boston’s first-round series against the Orlando Magic.

Though he remains a high-level defender and respected locker room presence, his age (he will be 36 by next postseason) and declining offensive output made him expendable, especially with Jayson Tatum set to miss significant time next season due to an Achilles injury.

On the other hand, Boston acquired Anfernee Simons from Portland. He is younger, more attack-minded, and most importantly, cheaper than Jrue Holiday. The 26-year-old guard averaged 19.3 points per game last season. Unlike Holiday’s long-term financial commitment, Simons’ expiring deal gives the Celtics immediate financial breathing room and potential trade flexibility. His scoring punch could help offset the expected absence of Tatum, and he fits well next to Derrick White in the backcourt—at least for now.

The Celtics also created a $4.1 million trade exception, which, despite being over the second apron, could still be useful under limited conditions due to the new CBA.

Boston’s Next Moves: Porzingis, Hauser, and More?

It is believed around the league that Boston has at least one more trade in them before the summer is over. Kristaps Porzingis, whose contract includes payment of $31 million next year, has appeared in several only off-the-board conversations. It is also noted that Boston are eye-balling Sam Hauser, as a low-cost shooting prospect that may be of interest.

To make the situation even more difficult, there are the contract situations of Derrick White and Jaylen Brown that need immediate addressing. White, as an important member of the Boston defense/backcourt, could also attract the interest of teams who need to compete immediately. Jaylen Brown, off a near-All-NBA season but needing a huge payoff, would not be out of the mix, and nothing seems out of the question as the Celtics remake the cap sheet under the eye of the Tatum recovery timeline.

People are now wondering whether Boston can fall into a temporary bridge year plan- in other words, they just have to remain competitive but stay out of the long-term pitfalls, and hope that Tatum’s return will make them contenders again.

Bringing Jrue Holiday on board appears as a big venture for the Trail Blazers. They once had his rights briefly in 2023, then sent him on a detour to Boston. But this time around, the Trail Blazers seem keen on keeping him. They need someone like him who can be a veteran presence and add some much needed defensive stability.

Holiday joins a young core featuring Scoot Henderson, Deni Avdija, Toumani Camara, and Donovan Clingan. While Henderson was expected to take over as the full-time point guard, the Blazers may see Holiday as both a mentor and a stabilizer. According to reports, Portland was looking to move on from Simons, in part to clear space in the backcourt for Henderson’s development.

Still, the financial commitment is significant: $104 million over three years for a 35-year-old guard, with potential redundancy in the backcourt. Portland is gambling that Holiday’s championship experience and elite defense can elevate a 36-win team to play-in relevance in a stacked Western Conference.

As Bobby Marks noted, this move reflects a shift in Portland’s approach: they are choosing roster certainty over cap flexibility. If the Blazers weren’t planning to re-sign Simons or chase big free agents in 2026, Holiday effectively becomes their marquee acquisition.

To Boston:

• Anfernee Simons: $25.9M (2024-25), $27.7M (2025-26, UFA)

To Portland:

• Jrue Holiday: $30M (2024-25), $32.4M (2025-26), $34.8M (2026-27), $37.2M (Player Option, 2027-28)

Boston eliminates $72M in future obligations and is projected to save up to $40 million in tax penalties in 2025-26. That’s assuming they continue to shave down the payroll further to get under the second apron, which will be necessary to avoid severe roster-building restrictions under the new CBA.

This move is far more strategic than sentimental. Jrue Holiday helped Boston capture Banner 18 and provided moments of brilliance on both ends of the floor. But the NBA is a cold business when it comes to long-term cap health, and Boston’s front office has chosen pragmatism over nostalgia.

To Portland, the acquisition is an odd patchwork of guidance and desire. They hope that the addition of Jrue Holiday will accelerate the process of their young core and that they have a chance to compete in the near future as well.

In the case of Boston, this is just the commencement. The Celtics remain far above the second apron, and rumors of potential trades involving Kristaps Porzingis, Sam Hauser, and others will continue to follow to a large degree as the team readjusts its future.

This much is certain: the Jrue Holiday trade represents a definitive line in the sand in Celtics-land: a shift, not just in the calendar, but in team focus, too: a shift, in other words, to roster realignment.