
Jrue Holiday is returning to the Western Conference after spending the last five years of his career with Boston and Milwaukee. The Celtics traded the two-time champion to the Trail Blazers in exchange for Anfernee Simons and two second-round draft picks on Monday, June 23rd, 2025, just one day after the NBA Finals concluded. Holiday will make $32.4 million next season, and his current deal will only become more expensive.
He missed out on an All-Defensive Team selection this past season—the first time since 2020. Going into a season where he will be 35 years old, Boston decided to be proactive and move off of Holiday’s contract while adding some youth in Anfernee Simons. What will be interesting to see is whether Jrue Holiday can assist the Portland Trail Blazers in their current rebuilding phase.