The Boston Celtics of the 2025-26 season are embarking on a transformative journey as they trade Jrue Holiday to the Trail Blazers in exchange for Anfernee Simons and two future second-round picks.

Holiday, who played a pivotal role in the Celtics’ 2024 championship run, was traded for several reasons:

• His current salary exceeds that of Simons by $5 million this season, and he is locked into three more expensive years of his contract, while Simons is on an expiring deal.
• The Celtics still have approximately $18 million above the second apron and aim to reduce it, indicating more roster adjustments are likely.
• At only 26, Simons provides a significant age advantage, bringing fresh energy to the lineup at a time when Holiday recorded his lowest average points per game since his rookie season and played in just 62 games.

While Simons may not be as strong defensively as Holiday, he brings a scoring capability that averaged 19.3 points per game in the 2024-25 season and can significantly impact the Celtics’ future, especially as they adapt to playing without Jayson Tatum for part of the upcoming season.

For further insights, one can look at the critical assessment of the trade’s implications conducted by analysts, which points out that the Celtics have potentially improved through this strategic move. Sam Quinn’s analysis raises questions about the Trail Blazers’ perspective and strategic objectives in this trade.