
The New York Knicks have been struggling since their NBA Cup victory in mid-December. They've gone 11-9 over that stretch, and the front office knows something needs to change before the February 5 trade deadline. The latest name to surface in trade discussions is one that carries serious championship credentials.
Marc Stein reported in his Monday Night Confidential newsletter that the Knicks have explored pathways to try to acquire Portland Trail Blazers guard Jrue Holiday. Stein framed the interest around two key points that keep coming up in league circles.
"The presumption that acquiring Holiday — if there's a way — would make the Knicks an even more attractive destination to Holiday's former Bucks teammate Antetokounmpo," Stein wrote.
The second reason is simpler
"New York is believed to hold a longstanding fondness for Holiday as a potential backcourt complement to Jalen Brunson," he wrote.
That fondness makes sense when you look at Holiday's resume. He won championships with Milwaukee in 2021 and Boston in 2024. He's made six All-Defensive teams and has been the kind of two-way guard that contenders chase when the games matter most. This season, he's putting up 15.3 points, 6.9 assists, and 4.5 rebounds in 19 games for Portland.
The simplest route involves sending Mikal Bridges and Mitchell Robinson to Portland. Bridges makes $24.9 million while Robinson earns $12.9 million, which gets close enough to Holiday's $32.4 million to make the money work.
There's also a more ambitious version of this trade floating around. A three-team deal would bring both Giannis Antetokounmpo and Holiday to New York. The framework has Karl-Anthony Towns heading to Milwaukee along with young prospects like Pacome Dadiet and Mohamed Diawara plus draft picks. Portland would get Bridges and Guerschon Yabusele in return.
The Knicks roster would look totally different, but all the more powerful.Holiday's six All-Defensive selections paired with Giannis' two-way dominance would fix the defensive issues that have plagued New York lately. Even the simpler deal still gives the Knicks Holiday's playoff experience and elite perimeter defense next to Brunson, which addresses a real need.
Here's where things fall apart. Start with the age and injury concerns. Bridges is 29 years old and hasn't missed a game in forever. Holiday is 35 and has played just 18 games this season because of a calf injury that kept him out nearly two months. This trade idea swaps a younger, healthier player who's available every night for someone who's already dealing with the wear and tear of a 17-year career.
Bridges is averaging 15.6 points, 4.4 rebounds, and 4.2 assists this season while playing every single game.
Robinson's been even more valuable in ways that don't always show up in the box score. He's averaging 9.1 rebounds per game and leads the entire NBA in offensive rebounding. Those second-chance opportunities have been the difference in close games all season, giving the Knicks extra possessions when they need them most.
Once he's gone, that production doesn't just magically get replaced by Holiday's defense, no matter how good it is.
The three-team deal has even bigger problems, starting with why Milwaukee would ever agree to it. They'd be trading Giannis, a 31-year-old generational talent who does everything at an elite level, for Towns, who's shooting 46.9 percent this season in a career-worst performance.
Towns doesn't provide Giannis' defensive impact or his ability to take over games on both ends. If the Bucks are actually moving their franchise player, they're getting way better offers than that.
For the Knicks, they'd be building around two guys in their mid-30s. Giannis is 31, Holiday is 35. The idea requires New York give up Bridges right as he's entering his prime, plus whatever young pieces, for a core that's already aging. That window closes fast, and if injuries hit, there's no flexibility.
Portland's timeline doesn't match up either. They got Holiday from Boston just seven months ago by sending out Anfernee Simons. The Blazers are 19-21 and trying to make a playoff push with their young core. Why would they turn around and flip Holiday for Bridges and Robinson or Yabusele when they just committed to having him as a veteran leader? It doesn't make sense unless someone's overpaying, and the Knicks don't have the assets to do that.
Then there's the money. Holiday is owed over $104 million through 2027-28. The Knicks are already hard-capped right up against the second apron. Taking on that contract for a 35-year-old means they can't make any other moves to add depth or can't pivot if something goes wrong. That's not how teams build sustained success.
The Knicks would be smarter to stick with what they have or look for smaller upgrades that don't gut the roster. Yabusele's name keeps coming up in trade discussions, and that's the kind of move that makes more sense right now.
Holiday's a champion who knows how to win. Nobody's questioning that. But giving up Bridges and Robinson while taking on a massive contract for someone who's 35 and already missed half the season? That's too steep a price for what you're getting back.
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