After the Portland Trail Blazers traded Anfernee Simons for Jrue Holiday early in the offseason, some expected Portland would immediately try to flip the veteran guard for more future-oriented assets. However, the Blazers have held fast — as Holiday’s introductory press conference in July reaffirmed — that they expect the new guard to play an important role in the 2025-26 regular season.

Just two months before the Blazers finalized the deal for Holiday, ESPN senior writer Baxter Holmes wrote an expansive profile on the decorated guard and how he became one of the NBA’s best defenders. Holmes wrote the piece as Holiday and the Celtics were still playing in the 2025 Eastern Conference Playoffs, attempting to win their second consecutive NBA Championship (an effort that ultimately ended in t

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