(photo via. Troy Wayrynen-Imagn Images | Troy Wayrynen-Imagn Images)
Brad Stevens cannot keep getting away with this.
In a late night trade, Brad Stevens and the Boston Celtics have agreed to send Jrue Holiday to the Portland Trailblazers for Anfernee Simons and two 2nd round picks (per Shams).
The 33 year old Holiday will be joining Portland for the second time, and just like his first stint, I expect him to be moved before the season begins. Portland now has a complicated roster especially at the guard position with former 2nd overall pick Scoot Henderson and Shadeon Sharpe leading the way.
For Boston, they gain a 26 year old guard who fits the timeline of their two stars Jaylen Brown and Jayson Tatum. Simons is an UFA in 2026 and is owed $26 million dollars over the next season.
It was very well reported that the Celtics were loading to make a large move this off-season. With the team well over the 2nd Apron and superstar Jayson Tatum sustaining an achilles tear that will likely sideline him the entirety of the 2025-2026 season, a move to wiggle under the apron was well on its way. With this move the Celtics duck below the 2nd apron mark and around $72 million over the next 3 years.
Simons averaged 19 points while shooting 42% from the field in his 2024-2025 campaign while knocking down 36% of his shots from deep. Simons adds additional ball handling and scoring to help fill Tatum’s absence for the upcoming season.
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