The Knicks’ ongoing search for ways to raise their ceiling ahead of the Feb. 5 NBA trade deadline has reportedly led them to at least explore a familiar name: Jrue Holiday.
In his “Monday Night Confidential” notes, Marc Stein reported “rumbles” that New York has explored pathways to try to acquire Holiday from the Portland Trail Blazers. Stein framed the interest around two themes that keep resurfacing in league circles: first, the belief that adding Holiday could make the Knicks an even more appealing landing spot for Giannis Antetokounmpo, Holiday’s former championship teammate in Milwaukee; second, New York’s long-running admiration for Holiday as a potential backcourt complement to Jalen Brunson.
Holiday, 35, is the type of player front offices chase when the games get heavy, an elite defensive guard with postseason scars and rings. He helped the Bucks win the 2021 title and was a key piece of Boston’s 2024 championship run, giving him a rare résumé as a two-time champion in this decade. He’s also expensive and under contract: Holiday is on a four-year deal in the $134–135 million range, which shapes any realistic trade math.
The wrinkle here is Portland’s perspective. The Blazers reacquired Holiday in the summer of 2025, and any decision to move him again would come down to timing, leverage, and whether Portland prefers future flexibility over keeping a veteran who can stabilize a young roster. For New York, the question is cost, and whether the Knicks would be willing to part with meaningful rotation pieces or draft capital for a win-now guard whose value is highest in May and June.
