Celtics trade Jrue Holiday for Anfernee Simons
The Celtics have traded point guard Jrue Holiday for Anfernee Simons and two second round picks. This comes after a dissappointing season where the Celtics lost in the 2nd round to the New York Knicks. This was always a likely outcome, even if the Celtics repeated, given how expensive the team would be. The dissappointing loss, along with Jrue already showing signs of decline and 3 more years averaging nearly $35 million per season, it was an easy choice.
During the 2024 season, Jrue was one of the best role players in the league, bringing his usual all defensive abilities, along with elite shooting and helping space the floor for a historic offense, shooting 42.9% from three, and a staggering 61.9% on corner threes. This trade was the final piece to thrust the Celtics into a dominant championship run, and it cannot be overstated how big he was for the 2024 team.
Image via @JWeinbachNBA
Unfortunately, things move fast in this league, and Jrue is a shining example of that. His corner three-point percentage fell off a cliff, shooting just over 30% in the 2025 season, and 35.3% overall on threes. His defense was still elite, but the offensive drop off was noticeable, and it carried over in the playoffs.
With Tatum's injury, the Celtics will not be anywhere close to seriously competing in the 2026 season, so salary had to be dumped, and Jrue carried a ton of extra salary. Anfernee Simons will have a $5 million lower cap hit and is on an expiring deal. Essentially, the Celtics get a better offensive player who is still young and has upside, on a cheaper deal, and if he does not perform well, the Celtics lose nothing, because of the 2 2nd round picks they gained in the trade.
While the Celtics could still look to flip Simons, for now let's assume he is staying on the team. The Celtics will have a back court of Derrick White and Anfernee Simons, two guys who get up a ton of threes, perfect for Mazzulla's offense. Simons is a career 38% thee point shooter, and from 2022-2024, his volume jumped to 8.5 3 point attempts per game and shot nearly 39%, but in 2025 he shot just 36%.
With the Celtics improved spacing, along with the team's ball movement, should allow Simons to get tons of clean looks. Simons will be playing in a luxurious middle ground, he is playing on a prove it deal, but the team's expectations will not be very high, so the pressure to be excellent should not affect his confidence and play like we have seen it do to other players.
This is a good start to the Celtics offseason, but there will be more moves, and Kristaps Porzingis will likely be next. These next two months will now reshape a new era of Celtics basketball.