New York Knicks, Jrue Holiday Can Benefit From Damian Lillard Trade Aftermath

Though Giannis Antetokounmpo is probably out of the question, the New York Knicks can still benefit from the trade that paired him with Damian Lillard.

Dame Time finally reached midnight in the Pacific Northwest.

The basketball-loving public's recurring nightmare of Damian Lillard fanfiction is finally over, as a three-team trade sent the longtime Portland Trail Blazer to the Milwaukee Bucks. Though he reportedly pined for the Miami Heat, Lillard appears to have accepted his Wisconsin-bound fate, one made easier to swallow with the promise of collaborating with Giannis Antetokounmpo.

As is tradition, observers have compiled a list of winners and losers from the deal. Those looking for a quick, lazy laugh will inevitably turn to the New York Knicks, who appear to have missed out on another superstar on the move. The Bucks fulfilling Antetokounmpo's request to take a return to the NBA Finals more seriously serves as a de facto sealing of his immediate fate barring full-on disaster. 

While no immediate move will match Antetokounmpo or Lillard's impact, the Knicks still stand to benefit from what comes next. 

For one thing, the idea of either Antetokounmpo or Lillard taking to Madison Square Garden's hardwood for opening night on Oct. 25 was a pipe dream at best. Even if Antetokounmpo was disgruntled, it felt like the Bucks had one more year to work with him no matter what. The Knicks could've made a Lillard trade work but it would've required a lot of maneuvering on their end.

Jrue Holiday (21) guards Knicks backcourt man Quentin Grimes (6) / Vincent Carchietta, USA TODAY SPORTS

With the fates of Antetokounmpo and Lillard decide, the focus now turns to what Portland will do with its own haul. ESPN Adrian Wojnarowski, who first broke news of the Lillard trade, hinted that the Trail Blazers aren't done dealing, namely mentioning that Jrue Holiday's fate is anything but sealed.

Holiday, a 2023 All-Star, is likely the biggest non-Lillard name involved in the trade. With his new employers more or less prepared to use 2023-24 as an extended research and development session (Wojnarowski says Portland is "committed to its young group of talented guards" that includes Shaedon Sharpe, Anfernee Simons, and rookie Scoot Henderson), Holiday doesn't have much of a Pacific Northwest purpose. 

On New York paper, trading for Holiday is burdened with the same issues that dragged down a Lillard deal: the Knicks are already flush with backcourt options and doubled down on that dedication by swapping Obi Toppin for Donte DiVincenzo in head coach Tom Thibodeau's nine-man rotation. If anything, the Knicks should be inquiring about DeAndre Ayton to foster the Julius Randle depth slot that Toppin left behind. 

If Portland was willing to accept something along the lines of Evan Fournier and their selection from the Knicks' draft pick cabinet, Leon Rose and Co. would be silly to let that moment slide. Mike Vaccaro of the New York Post, for example, suggested a deal that would include Fournier, Quentin Grimes, Isaiah Hartenstein, DaQuan Jeffries, Isaiah Roby, and two draft picks. 

But Portland will no doubt want a little more if they're going to go all in on a rebuild. Any deal that involves elite talent will have to send elite talent, and that will likely include 23-year-old RJ Barrett. Holiday is undoubtedly playing some of the best basketball of an accomplished career, but he just turned 33. Are the Knicks willing to enjoy a few years of prime Holiday at the cost of Barrett's upside, all for what could amount to merely moving a few floors closer to the Eastern Conference penthouse occupied by Milwaukee, Miami, and Boston? 

Holiday's defensive prowess and more, however, could make the deal too sweet to pass up.

Thibodeau has gained a reputation as an old-school coach, one who favors veteran talents that prioritize two-way showcases over massive scoring efforts. Holiday as made five All-Defensive teams and has averaged over six assists a game since entering the league with Philadelphia in 2009. On his shelf next to his Milwaukee championship ring from 2021 is a Sportsmanship Award and three of the last four Teammate of the Year honors. 

The one thing working against the Knicks is the cost. Retaining all of last year's starting five will be too much to ask for and the draft pick savings account should only be exhausted when a true needle-mover is on the line. 

Is Holiday that man? Neither side will have an extended opportunity to impress each other, as Holiday has a $37 million player option he'll more than likely pass. The Knicks have enough to worry about come the 2023-24 season and impressing Holiday enough to stay for the long-term would be an intriguing, if not weighty, subplot.

One thing's for sure: whatever team lands Holiday have reasons to celebrate. Time will tell if the Knicks are capable of pulling it off.