The New York Knicks reportedly have interest in acquiring Jrue Holiday. The Portland Trail Blazers own a bunch of the Milwaukee Bucks' future draft picks, have interest in New York's Mikal Bridges, and would like to use any trade involving Giannis Antetokounmpo as a way to improve their roster. By landing Holiday and Milwaukee's draft picks in a deal involving Bridges ahead of the deadline, the Knicks could have a unique offer for Giannis that just might land the Greek Freak in the Big Apple by the offseason – or maybe even earlier.
Knicks' interest in Holiday could be precursor to Giannis trade
In a Monday night edition of The Stein Line, NBA insider Marc Stein covered the Knicks heavily with the NBA's trade deadline approaching on February 5. The scribe wrote about All-Star center Karl-Anthony Towns and the chances that New York moves him ahead of the deadline, as well as a follow-up on Jake Fischer's Sunday report for his newsletter.
"Another concept that keeps coming up: Rumbles that the Knicks have explored pathways to try to acquire Portland's Jrue Holiday. 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: 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 Antetokounmpo; 2) New York is believed to hold a longstanding fondness for Holiday as a potential backcourt complement to Jalen Brunson," Stein wrote.
This lays the groundwork for some interesting changes ahead of the trade deadline. If the Knicks think it's possible that they can make a trade involving them sending out Bridges but getting both Holiday and Milwaukee's draft capital in return, that changes the game with regard to any future pursuit of Antetokounmpo's services.
It also lines up perfectly with a rumor that NBA analyst Zach Lowe said he was hearing on an insane trade rumor that involved the Knicks landing both Antetokounmpo and Holiday in the same deal. Whatever Lowe was hearing, it seems like he heard it correctly.
Even if they had to revisit trade talks with the Bucks in the 2026 offseason, Stein seems to think that an acquisition of Holiday would make Giannis even more interested in playing home games at Madison Square Garden. The team would have the salaries required to make a deal work and could sell Antetokounmpo on playing with both Brunson and Holiday, as well as every other player that doesn't get sent out in any potential deals.
It's unknown if Portland would want to use the Bucks' draft capital to turn someone like Holiday into someone like Bridges, especially before any deals involving Antetokounmpo himself go down. But if they think the Knicks are going to be the team that eventually lands him, they might be best served doing business with them now and trying to pry whatever young players they're interested in from New York's roster in the process of swapping Holiday for another talented two-way player that is six years younger.