With the NBA trade deadline looming on February 5, front offices across the league are working the phones, weighing short-term moves against long-term vision. And while all eyes are understandably on the Giannis Antetokounmpo situation in Milwaukee - the kind of franchise-altering headline that sends shockwaves through the league - there’s another name quietly gaining traction in New York: Jrue Holiday.
Holiday returned to Boston on Monday for the first time since being dealt to Portland, and while the Celtics faithful showed their appreciation, it was the words from his former teammates that really hit home. Payton Pritchard summed it up best after Boston’s 102-94 win over the Blazers: “It was such a pleasure being his teammate.
I learned so much… just a great human being. Obviously, a wonderful basketball player, but the teammate he was and just to be around, I'm very grateful for it.”
That kind of praise doesn’t come lightly in a league where locker room chemistry can make or break a playoff run. And it’s exactly the type of intangible that has the Knicks seriously eyeing Holiday as the trade deadline approaches.
According to veteran NBA insider Marc Stein, New York has been exploring ways to pry Holiday from Portland. There are two big reasons why this makes sense for the Knicks - and both go beyond just what Holiday brings on the court.
First, there’s the not-so-subtle connection to Antetokounmpo. Holiday and Giannis won a title together in Milwaukee, and the idea of reuniting them in New York is more than just fantasy basketball. If the Knicks can land Holiday now, it could be the first domino in a much larger plan - one that ends with a two-time MVP wearing orange and blue.
Second, the Knicks have long admired Holiday as a potential backcourt partner for Jalen Brunson. And it’s easy to see why.
Brunson has been electric offensively, but his presence - along with Karl-Anthony Towns - creates defensive vulnerabilities that opposing teams have been happy to exploit. The Knicks currently sit 18th in defensive rating, and that’s a red flag for any team with real championship aspirations.
Enter Holiday, who at 35 is still one of the league’s most dependable two-way guards. He doesn’t just play defense - he changes games with it.
His ability to guard multiple positions, fight through screens, and make smart rotations would immediately raise the Knicks' defensive ceiling. Whether he’s sharing the floor with Brunson, Towns, or both, Holiday’s presence would help stabilize a unit that’s been inconsistent all season.
Of course, there’s the financial side of it. Holiday carries a hefty $34.8 million cap hit for the 2026-27 season and holds a player option worth $37.2 million the year after.
That’s not pocket change, even for a big-market team like New York. But with owner James Dolan reportedly labeling this season as “championship-or-bust,” the front office may be willing to absorb that cost if it means a legitimate shot at ending a title drought that stretches back to 1973.
The Celtics, for their part, would prefer to see Holiday stay in Portland - far away from the Eastern Conference arms race. They know better than most what kind of impact he can have on a team’s title chances. He was a key piece in their own recent run, and his leadership, professionalism, and defensive tenacity left a lasting impression in Boston.
For the Knicks, the stakes are clear. Holiday isn’t just a short-term upgrade; he’s a culture setter, a playoff-tested veteran who can help Brunson carry the load and elevate the team on both ends.
And if adding him now helps lay the groundwork for a Giannis pursuit down the line? That’s the kind of long game that could change the trajectory of the franchise.
New York has the assets, the ambition, and the urgency. Now, it’s just a matter of whether they can make the pieces fit - and whether Portland is willing to pick up the phone.