Knicks Can Make Damian Lillard Trade Work, But Is It Worth It?

The New York Knicks could somehow justify a Damian Lillard trade, but it would require a way too many adjustments on their end.

If the New York Knicks engage in a trade that would serve as an offseason buzzer-beater, it'd perhaps only be appropriate if Portland Trail Blazers guard Damian Lillard was involved.

By now, Lillard's name has surfaced in so many hypothetical trades that the basketball-loving public is likely numb to such gossip. No Lillard tweet ... or "post," as the case may be ... will pique the community's interest until the Blazers open one with some form of "OFFICIAL" and reveal Lillard's long-awaited fate. 

Lillard's never-ending trade story took an intriguing turn this week, as a report from Marc Spears of ESPN said that a "mystery team" from the Eastern Conference has expressed interest in moving clocks to "Dame Time." 

Whether that squad in Spears' question is the Knicks is anyone's guess. But Manhattan, of course, is hardly any stranger to transactional gossip involving high-octane talents. Even in a muted offseason, one where the biggest transaction has been the de facto flip of Obi Toppin for Donte DiVincenzo, the Knicks' name has been planted in the transactional grapevine.

For all intents and purposes, the Knicks appeared to have excused themselves from the Lillard proceedings. Adding Lillard, after all, would seem redundant in an offseason where DiVincenzo will have to fight for minutes alongside Quentin Grimes and a potential Immanuel Quickley farewell tour.  

With DiVincenzo in tow, the team's backcourt picture is already packed to the point where an $18 million three-point specialist in Evan Fournier and a defensive standout like Miles McBride are sidelined entirely. Knicks management was reluctant as it was to part with Grimes in the ultimately futile Donovan Mitchell chase. To top it all off, the Quickley situation is far from resolved as he seeks new life beyond his rookie contract. In all honesty, if the Knicks were honestly going to go after a Trail Blazer, they'd perhaps be better off inquiring about Jusuf Nurkić or Jerami Grant to back up Julius Randle. 

The new intel from Spears, however, will no doubt spark the Knick fan's imagination. A trade can work ... but involves a lot of adjustments on the Knicks' end for better and worse.

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Have the Hart

Even with a crowded backcourt, there's enough to justify the Knicks' continued grazing in Lillard's pastures. For one thing, New York just re-upped with former Blazer Josh Hart for the long term.

Lillard has, to his credit, been a good sport during a roller-coast tenured in Portland, one that has flirted with, but never truly attained, the highest height and the lowest lows. Dealing Hart to the Knicks at the trade deadline, however, appeared to draw his ire. 

From the moment Hart left, Lillard appeared to be planning a reunion.

“Josh is a really good player,” Lillard said after the trade, per Aaron Fentress of OregonLive. “You have to know that he has an option. He’s probably going to opt out of the deal that he has now and you have to assume that he’s going to be wanted on the open market, and there’s a chance that you lose a player like that if you’re not able to match that number. 

"So, it’s either that or you find an opportunity where you can position yourself to maybe do something else significant, he continued. "Instead of just having a loss of a significant player. I know that he liked being in Portland. He wanted to be in Portland. When you get people to come here and know that they want to be here, but the business takes over, it’s just unfortunate.

New York obtained Hart at the trade deadline in exchange for Cam Reddish, Ryan Acridiacono, Svi Mykhailiuk, and their regularly scheduled first-round pick in the most recent draft. Save for the pick (which became Kris Murray at 23rd overall), none of them have stayed in Portland (Arcidiacono has already made his way back to New York).

Hart apparently hasn't forgotten Lillard's words, reaching out to Lillard on social media shortly before he defied his former teammate's expectation and agreed to sign his $12.9 player option that came over from Portland for the 2023-24 season. That player option later became an eight-figure contract extension, one that's destined to keep Hart in Manhattan until 2028.

If Lillard is truly serious about collaborating with Hart again, the Knicks could insert themselves into the conversations. 

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Young Guns For Hire

Lillard reportedly has his heart set on taking his talents to South Beach and joining the Miami Heat. But when Miami's best offer is headlined by Tyler Herro ... decent enough but hardly suitable to be a selling point in a potentially grueling Pacific Northwest rebuild ... Plan B tends to linger as a talking point. 

Knicks fans don't need to be reminded about their expansive youth reserves and draft pick cabinet. Viewing highlight reels of Grimes and Quickley, and even RJ Barrett, is burdened with the knowledge that every minute in blue and orange could be their last. The past two NBA Drafts have ended with the Knicks making a single pick (departed 2022 second-rounder Trevor Keels), despite loading up on future choices. 

The Knicks' restraint when it comes to exorcising themselves from the Mitchell sweepstakes proved prudent and yielded the franchise's most lucrative season in a decade. Frequent trips to the conference semifinals, however, hardly prove to hold lasting satisfaction ... look no further than the ongoing drama in Philadelphia. 

The Knicks have proven they can at least stay out of the purgatorial Play-In Tournament with their current core. But a key to the Eastern Conference penthouse will require some extra help ... and with help comes sacrifice, a hint that not everyone who contributed to the effort that pulled the Knicks out of the mire of rebuilding won't get to stick around to partake in the ultimate reward.

Barrett, Grimes, and Quickley have all proven their NBA worth and longevity. But whether the latter comes in New York remains to be seen.

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End the Quickley Quagmire Quickly

Only the 21st century Knicks could be blessed with one of the Association's finest rising depth stars and have his continued prescience linger as a curse. The Knicks have a major decision to make on Quickley, their most consistent backcourt contributor beyond Brunson. Quickley may be a Sixth Man ... but it has been strongly implied that he wants nine figures once he's able to break away from the original rookie deal bestowed to him upon his draft night arrival in 2020. 

Beyond Brunson (and Hart, whose new extension legally keeps him out of trades), there's no one untouchable on the Knicks' roster. Quickley's unique blend of an expiring contract, rising talent, and situation on a crowded depth chart makes him one of the most intriguing pieces any bartering team can offer.

Quickley was a Sixth Man of the Year Award contender last season and will likely stand as one of the favorites for this year's edition. But the hard reality for anyone who has shelled out for his No. 5 jersey is that such title-holders aren't often afforded longevity. 

Dating back to 2013's award (won by then-New Yorker JR Smith), every triumphant Sixth Man (including recurring winners Jamal Crawford and Lou Williams) has been on at least his third team and far removed from his rookie contract. That perhaps makes Quickley's rise to power all the more impressive but it puts the Knicks in a relatively awkward spot. 

There are obviously 28 destinations that can vie for Quickley's services, but Portland would be, bar none, one of the most attractive. The backcourt hole that Lillard would hypothetically leave behind, for example, could be instantly filled by Quickley, whose finest efforts of the 2022-23 season came when he filled in as a starter for Brunson, Barrett, or Grimes. With the Blazers rebuilding to the tune of Scoot Henderson, Shaedon Sharpe, and Anfernee Simmons leading the way, Quickley would be an undisputed top option for the first time in his career and undoubtedly well worth the nine figures he so desires.  

But Is It Worth It?

Ultimately, staying the course is the Knicks' best path going forward, at least for now. If they're going to add a star, they're far better off waiting out either Giannis Antetokounmpo, Joel Embiid, or even Mitchell (again). 

The greatest hidden benefit of the Knicks' departure from the Mitchell conversations was the fact that it stopped the team from hitting fast-forward on the latest iteration of the metropolitan rebuild, one that's armed with legitimate hope thanks to Brunson's breakout. By sticking with Brunson as the headlining addition, the Knicks perhaps enjoyed the closest thing they'll ever have to a truly peaceful season: with many placing Play-In purgatory as their ceiling, the team was able to grow and develop in peace. 

Compared that to Mitchell's eventual destination in Cleveland, which was pushed forward with a trendy young foundation that had won 44 games the year before: even with the proverbial "one star away" piece added and some dubious pre/post-LeBron James history erased, the Cavaliers struggled to gain entry into the Eastern penthouse, setting them up with a matchup of destiny against a fifth-seeded Knicks group packed to the brim with a sense of healthy reckless abandon. 

The Knicks took that series in five games, securing a successful season of overachievement that even a loss to eighth-seeded Miami couldn't erase.

If the Knicks trade for Lillard now, they become the Cavs. The very last thing the Knicks need right now is expectations, or at least those that place them beyond the relative safety of the conference semifinals. New York is more or less running things back with the same group that won 47 games last year. They still don't have a key to the penthouse, but they are at least on the elevator.

Adding Lillard to the fold, however, would move them to Wonkavator speeds and there's nothing to indicate that the Knicks are ready for such responsibilities quite yet. There will undoubtedly be more eyes on the Knicks this season (the NBA's national television partners certainly took notice) but New York has to soak in and power up for as long as they linger at the cusp of the national spotlight.