The Portland Trail Blazers are in a unique spot leading up to the Feb. 5 trade deadline. They have been named as potential buyers, as adding another piece to make a playoff push suddenly makes perfect sense. At the same time, they should also consider being sellers when it comes to two key pieces: Jrue Holiday and Jerami Grant.
Portland has two overpaid veterans on its roster and should explore ways to shed one of those contracts, primarily to create financial flexibility to renegotiate and extend Deni Avdija's contract down the road. One way to achieve this would be to send Holiday to the New York Knicks.
Marc Stein recently reported on The Stein Line that the Knicks have "explored pathways" (subscription required) to acquiring Portland's veteran guard.
Should Portland trade Jrue Holiday?
Giannis Antetokounmpo trade talks have only intensified as the deadline has gotten closer, and the Knicks being a favorite landing spot could factor into their interest in acquiring Holiday. Additionally, Holiday's positional versatility makes him an ideal pairing for just about any star in the league, including New York's Jalen Brunson.
"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 reports.
The Blazers have been circulating in trade rumors as of late, with the Knicks emerging as a potential trade partner. Jake Fischer previously reported on The Stein Line that Portland is exploring ways to capitalize on a Giannis-Knicks trade (subscription required) as a possible third party, especially given its leverage with Milwaukee's future draft capital thanks to the Damian Lillard deal.
This latest Jrue Holiday-Knicks connection is much more surprising. It's important to note that Stein adds that some have insisted that the Knicks are focused on making a smaller deal centered around trade candidate Guerschon Yabusele. So this theoretical Holiday trade largely depends on how the Giannis-Bucks situation unfolds. The Knicks would be much more inclined to sacrifice assets for Holiday and take on his contract if he were only a stepping stone to landing a much bigger piece.
The Giannis-Knicks rumors are already complicated enough, so attempting to figure out Portland's potential role as a facilitator adds layers to an already messy situation. Regardless, it's encouraging that Holiday still seems to have trade value around the league.
Portland faces a challenging decision of whether to part ways with one of their best players right when they're looking to make a playoff push, but it's a good situation for them to be in.