The Portland Trail Blazers are in quite an interesting position this season. They are fighting for a Play-In spot in the West, and could potentially even make it up into the top six, but at the same time, teams could be interested in the pieces they have. If they decided to sell, they could get back some decent value and set themselves up even better for the future.
One of the players whom they could maybe look to trade, despite his elite on-court value, is Jrue Holiday. Marc Stein of The Stein Line reported that the New York Knicks have shown an interest in trading for Holiday. If that trade ends up happening, the Blazers would have the chance to do the funniest thing ever.
They could trade Josh Hart or Mitchell Robinson to another East contender.
Blazers could turn Knicks' Jrue Holiday trade into nightmare
These were the reasons Stein gave for the Knicks’ potential interest in Holiday:
“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.”
If the Knicks did make a deal for Holiday, the package would almost certainly have to be Hart and Robinson, purely from a financial standpoint.
So, if New York did add enough draft capital to make that type of deal happen, the Blazers could turn around and do what they did to the Milwaukee Bucks in the Damian Lillard trade.
Portland traded Lillard to the Bucks for Holiday, then turned around and gave Holiday to the Boston Celtics—a direct East competitor to the Bucks. Boston went on to win the championship.
If the Blazers trade Holiday to the Knicks, they could turn around and trade Hart or Robinson to another East contender (like the Celtics, Detroit Pistons, Toronto Raptors, or Cleveland Cavaliers).
New York would probably get better, but so would the teams they are competing against.
Obviously, Portland probably isn’t eager to trade Holiday, but if they do, and if the Knicks get him, the Blazers could make the deal turn into a nightmare for New York.