BOSTON – The Boston Celtics have officially moved on from veteran guard Jrue Holiday, ending months of speculation about his future. According to Shams Charania of ESPN, the Celtics traded Jrue Holiday to the Portland Trail Blazers in exchange for sharpshooter Anfernee Simons and two second-round picks. The deal signals a strategic shift for Boston, especially with star forward Jayson Tatum expected to miss the entirety of next season.
Celtics Trade Jrue Holiday for 38.1% 3-Point Flamethrower
Jrue Holiday’s Tenure in Boston Comes to a Close
Holiday, a respected two-way guard, played a crucial role in helping the Celtics win a championship last year. While known for his elite perimeter defense, Holiday struggled to find a consistent scoring rhythm in Boston’s crowded offensive hierarchy. He averaged 11.1 points per game and shot 35.3% from beyond the arc—his lowest three-point percentage since the 2019–2020 season.
Holiday’s offensive output declined largely due to his role as a fourth or fifth option behind Boston’s stars. In Milwaukee, where he earned All-Star and All-Defensive honors, Holiday operated with more freedom. His limitations in Boston reflected less on his talent and more on the team’s structure.
Holiday can still impact winning at a high level, albeit not as consistently as before. Approaching his late 30s, he can’t be expected to perform at an elite level in every game.
Celtics Acquire Simons, a Premier Shooter
The Celtics receive 25-year-old Simons, a dynamic guard known for his perimeter scoring. Simons averaged 19.3 points per game last season and shot 36.3% from three-point range. Despite a slight dip, his career mark from distance stands at an impressive 38.1%.
That number is significant for a Celtics team that thrives on spacing. Boston’s front office must believe Simons can slot into a key scoring role, particularly with Tatum sidelined. With better spacing and playmakers around him, Simons’ efficiency could rise again. His addition adds youth and scoring versatility to a roster that is adjusting to an uncertain short-term outlook.
Simons has one of the purest shooting strokes in the league. He just needs the right environment to thrive. For Boston, that environment may already be in place.
Portland’s Intentions Remain Unclear
It’s uncertain whether the Trail Blazers will keep Holiday or use him as trade bait once again. This isn’t Holiday’s first stop in Portland. He was briefly a Blazer following the Damian Lillard trade before being rerouted to Boston.
Now back in Portland, Holiday could serve as a mentor to Scoot Henderson, the No. 2 pick in 2023. With Henderson expected to be a centerpiece for the future, a year under Holiday’s wing could be valuable. Still, Portland could move him again, depending on market demand.
The Dallas Mavericks and Sacramento Kings have already expressed interest in Holiday. Dallas, in particular, needs a short-term solution at point guard while Kyrie Irving recovers from an ACL injury. With Jrue Holiday’s Celtics chapter over, a new one could quickly begin in Texas or California.
A New NBA Offseason Era
The trade marks another major domino in an already frantic NBA offseason. Desmond Bane was recently shipped to the Orlando Magic while Kevin Durant landed in Houston hours before Game 7 of the NBA Finals. Now, Jrue Holiday’s time on the Celtics has concluded, and both Boston and Portland find themselves pivoting in different directions.
Boston gains salary flexibility and an elite shooter who fits their evolving identity. Portland acquires a veteran who can either anchor young talent or become a valuable trade chip.
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