Trade package Knicks would need to land Damian Lillard, and where New York should draw the line

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Damian Lillard treated image in Oregon Blazers jersey
Damian Lillard treated image in Oregon Blazers jersey

Damian Lillard, one of the league’s top point guards, may be looking for an out from his current team, the Portland Trail Blazers, according to a report by Yahoo’s Chris Haynes. Should this rumor come to fruition, it would undoubtedly enamor the Knicks front office, stockpiled with assets and looking to build on a surprise fourth-seed finish in the East.

We’re still a ways away from anything materializing in this situation, but with only marginal upgrades available in free agency this summer and no stars demanding a trade at the moment, there’s no question New York is doing their due diligence on Lillard. If he becomes available, 29 teams will flock to the scintillating six-time All-Star who’s added the casual halfcourt pull-up to his game and one will pay the massive price of obtaining him. But what will that price be, and should the Knicks pay it?

To answer those questions, we have to look to recent superstar trades for reference. Just this season, the Houston Rockets dealt perennial MVP candidate James Harden to the Brooklyn Nets. New York’s crosstown rival had to give up the following: Jarrett Allen, Caris LeVert, Taurean Prince, three first-round draft picks and four first-round swaps. In 2019, Paul George became a Los Angeles Clipper for the small price of five unprotected first round picks, two first round swaps, Danilo Gallinari and Shai Gilgeous-Alexander.

Based on past evidence involving Lillard-caliber stars traded mid-contract, trading for Lillard will cost the Knicks everything. Not everything in a literal sense, but nearly every bit of draft capital and future potential they own. An “everything” trade would include: RJ Barrett, Immanuel Quickley, Julius Randle, Kevin Knox, Obi Toppin, Mitchell Robinson, five unprotected first-round picks and three first-round swaps.

This would leave New York with absolutely nothing but Lillard, which barring promises from fellow superstars that they’ll join up doesn’t seem ideal. The Knicks likely won’t deal Randle, and will fight like hell to keep their prized prospects, namely Barrett. However, they won’t be the only team negotiating with Portland.

Many teams can also offer up their entire draft stashes, including Oklahoma City, who can theoretically double up whatever picks New York offers up, though that would be unlikely. The biggest threat to the Knicks will be better kickers offered on top of other teams’ picks. Boston can offer Jaylen Brown and picks to the Blazers, ditto for New Orleans and Brandon Ingram or Philadelphia and Ben Simmons. So if it’ll take more than eight picks outright, how far should the Knicks go in losing their prospects to acquire Lillard?

Assuming Randle is off the table and Knox holds little value in these talks, that leaves Barrett, Quickley, Toppin and Robinson. Which of these, if not all, Portland (or New York) draws the line at may decide these negotiations off the bat.

Barrett is undoubtedly the best prospect of that list by a wide gap, younger and better than the rest of his peers. He’s coming off a breakout season as the second-leading scorer on a playoff team, in which he showed off his development as a shooter, creator and defender. Quickley and Toppin didn’t show enough in their rookie years to imagine them with star potential, while Robinson carries an injury bug that might turn teams off.

Naturally, this makes Barrett the potential dividing line. Barrett and those mountain of picks could nab Lillard, but giving up their most prized prospect might be too high a cost for the Knicks. If that’s the case, the Blazers may ask for all three of the remaining guys, which would mean giving up on one top-10 pick and two certified late-draft steals, no easy things to come by.

Either way, it’s clear any path to contention involving Lillard will cost an arm and a leg, if not some internal organs as well. This is a stars league, and you need stars to win in it. Few measure up to Lillard in terms of performance. Many will want to join what Leon Rose and Tom Thibodeau are building if Lillard and Randle are there as foundational blocks.

On other hand, if the Knicks are confident and have intel they can get one of Lillard’s caliber via the draft, free agency, or a smaller deal, maybe they pass on this opportunity. Lillard will be 31 next month, and this franchise has seen a few similar trades we don’t need to name again go awry.

Luckily this isn’t a franchise-altering decision the Knicks have to make yet. Should the time come, New York has a pool of assets to make the right move, one way or another, and that’s a good problem to have.