James Dolan, Knicks
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(3rd L-R) Executive chairman and CEO of The Madison Square Garden Company and executive chairman of MSG Networks James L. Dolan, model Marcela Braga and Tao Group partner Jason Strauss attend a game between the New York Knicks and the Phoenix Suns during the 2019 NBA Summer League.
After silencing a restless home crowd with back-to-back wins to climb out of a 2-9 skid, the New York Knicks find themselves once again at the center of mounting trade speculation as the front office weighs how aggressively to pursue a championship-or-bust season.
The latest development comes from NBA insider Marc Stein, who reported Monday that the Knicks have explored pathways to bolster their backcourt by targeting Portland Trail Blazers guard Jrue Holiday, a two-time NBA champion.
“Another concept that keeps coming up: Rumbles that the Knicks have explored pathways to try to acquire Portland’s Jrue Holiday,” Stein wrote in The Stein Line.
Why the Knicks Are Drawn to Jrue Holiday, per Marc Stein
Jrue Holiday, Jordan Clarkson, Knicks
GettyJrue Holiday of the Portland Trail Blazers drives the ball against Jordan Clarkson of the New York Knicks.
Stein outlined two primary reasons behind New York’s interest in the 35-year-old veteran, who recently returned after missing nearly two months with a right calf strain.
“There are at least two clear reasons why New York would have interest in a player who helped both Milwaukee and Boston win championships this decade,” Stein wrote. “1) 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 [Giannis] Antetokounmpo; 2) New York is believed to hold a longstanding fondness for Holiday as a potential backcourt complement to Jalen Brunson.”
Holiday’s defensive pedigree and postseason experience align with what the Knicks believe they lack most. Under first-year coach Mike Brown, New York’s defense — once its calling card — has slipped to 18th in the league, a troubling sign for a team with title aspirations.
Big Question: Will Knicks Push All-In Midseason?
Despite the fit, Stein questioned whether the Knicks are prepared to make a seismic move before the trade deadline.
“Once again, though, it must be asked: Are the Knicks truly willing to take big swings halfway through the season after Dolan so recently proclaimed the Knicks’ locker room to be the most ‘copacetic’ he has ever seen — while also declaring this season to be championship-or-bust — in that WFAN radio appearance?” Stein wrote.
Owner James Dolan’s comments underscored both stability and urgency, leaving uncertainty about how far New York is willing to go now versus waiting until the offseason.
Mikal Bridges’ Name Surfaces as Portland Interest Revealed
Stein’s report on Holiday follows closely on the heels of separate reporting from Jake Fischer, Stein’s colleague at The Stein Line, who revealed Portland’s long-standing interest in Knicks forward Mikal Bridges.
“League sources say Portland has long admired New York’s Mikal Bridges going back to Damian Lillard’s first stint as a Blazer,” Fischer wrote over the weekend.
The timing is notable, coming as Bridges continues to navigate an uneven offensive stretch.
Bridges’ Recent Struggles Add Fuel to Speculation
Bridges scored nine points on 3-of-16 shooting in Saturday’s 112–109 road win over the Philadelphia 76ers, going 1-for-9 from three-point range. After missing six straight shots, he was benched for much of the fourth quarter as New York closed with a different lineup.
The performance reflected a broader trend. After a strong October — averaging 19.0 points per game while shooting 48.1 percent from three — Bridges’ efficiency has dipped sharply.
In January, he is averaging 14.3 points on 34.8 percent shooting from beyond the arc. His season scoring average of 15.8 points is his lowest since the 2021–22 season.
While the Knicks have remained publicly committed to Bridges as a core piece, the production dip has fueled outside speculation.
What a Jrue Holiday Trade Could Cost the Knicks
A potential Holiday deal would likely require Bridges, Guerschon Yabusele, and an additional salary filler to satisfy matching requirements.
Given that New York surrendered five first-round picks and a pick swap to acquire Bridges, any deal involving him would almost certainly require draft compensation coming back from Portland.
Bridges, who signed a four-year, $150 million extension in August, becomes trade-eligible on Feb. 1, adding a firm date to the timeline.
Knicks at Crossroads as Deadline Nears
With momentum finally stabilizing and expectations firmly set on contention, the Knicks face a familiar dilemma: preserve continuity or swing for championship equity.
Whether that swing comes in the form of a Jrue Holiday pursuit remains to be seen. But as the trade deadline approaches, league insiders believe New York’s actions — or restraint — will define not just this season, but the direction of the franchise.