In a blockbuster move that shook up the NBA, the Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks.
This trade marks the first major deal since the 2025 NBA Finals, and it raises questions about the future of both teams. Here’s an in-depth look at how each side fares in this surprising trade.
Boston Celtics: A
The Celtics are giving up Jrue Holiday, a veteran All-Star guard, and getting Anfernee Simons in return. At 35 years old, Holiday’s decline was evident in the previous season
Despite still being a strong defender, his age and hefty contract ($32.4 million in the 2024-25 season, $34.8 million in the next) were likely weighing on the Celtics’ salary cap. With Jayson Tatum leading the team, Boston was in need of flexibility, and this deal provides that.
Holiday still holds value but is arguably not worth the expensive salary he commands for a team like the Celtics that has championship aspirations and needs to manage cap space. Boston’s primary goal in this deal is cap relief, and by shipping out Holiday, they shed the burden of his salary.
The two second-round picks are valuable assets, but the real win comes with the acquisition of Simons. At just 26 years old, Simons is a promising player, averaging 20.7 points per game over the last three seasons and possessing a potent three-point shooting ability.
He could help fill a void in Boston’s offense, especially with Tatum sidelined temporarily. Simons is a young player with room to grow, which is a key win for Boston in this deal.
In summary, the Celtics come out on top in this trade. They get much-needed cap relief and a promising young guard without giving up any significant assets for their future. This is a win-win for Boston.
Portland Trail Blazers: C-
The Portland Trail Blazers, on the other hand, took a much riskier approach. They acquired Jrue Holiday in an effort to balance their roster and aid the development of their young core, including Shaedon Sharpe and Scoot Henderson.
While Holiday’s veteran leadership could prove valuable to the team’s young players, the Blazers’ decision to bring him in is questionable for several reasons.
Holiday’s age (he’s entering his 35th season) and salary make this an odd fit for Portland, a team that is still in a rebuilding phase. Portland hopes that Holiday’s presence can help the young guards develop, similar to how Chris Paul helped Shai Gilgeous-Alexander in Oklahoma City.
However, given the financial commitment involved, it’s a move that could backfire. The Blazers will be on the hook for over $73 million in combined salary for Holiday and Jerami Grant by the 2027-28 season, which could severely limit their flexibility moving forward.
Additionally, Simons was a valuable asset for the Blazers, and trading him for a player on the decline doesn’t appear to be a wise decision. While Holiday is still a solid defender, his offensive game has been inconsistent, and his aging body could struggle in Portland’s up-tempo system. Plus, the Blazers had other options for adding veteran leadership without committing long-term money to an aging player.
On the positive side, Holiday’s defensive capabilities will help strengthen a Portland defense that improved post-All-Star break, but his fit alongside Henderson and Sharpe is uncertain. Portland may hope that the presence of Holiday will accelerate their rebuild, but the downside here is significant, especially given the long-term financial implications.
Boston Celtics: The Celtics win this trade by shedding Holiday’s contract while adding a promising young guard in Simons who could fit well into their system. They get cap flexibility and two second-round picks, making this an overall A for Boston.
Portland Trail Blazers: The Blazers took a gamble on a declining Jrue Holiday, hoping his leadership and defense will help their young core. However, the financial commitment, combined with the fact they gave up Simons, makes this a questionable move. Given the long-term implications, Portland earns a C- grade.
