Damian Lillard wants to move on from the Portland Trail Blazers after nine seasons in the City of Roses. If he's going to be traded, there's only one spot that makes sense. Lillard and the New York Knicks are a perfect match.
Lillard reportedly has interest in the Knicks and, given their current roster situation, there's no doubt New York would have interest in him. The Leon Rose era needs a jump-start and importing a star like Dame would give it exactly that.
Lillard is a six-time All-Star and a five-time All-NBA guy and at 31 he's still performing at peak level. During the 2020-21 season he was third in the NBA in points per game (28.8), seventh in assists (7.5) and ninth in PER (25.65), while averaging 4.2 rebounds and hitting 39.1 percent of his 3-point shots. He's an elite scoring guard, something the Knicks haven't had in years.
Perhaps more importantly, Lillard is a showman. Other than Stephen Curry, no one in the NBA goes nuclear the way Dame does. He's eminently watchable and entertaining as hell. He would be a perfect fit for the bright lights of Madison Square Garden.
Portland isn't going to give Lillard away. He's a star about to begin a four-year, $196 million contract extension next season. It will take a lot for New York to make a deal and it might even take a third team to make this work.
Any trade will almost certainly start with the Knicks surrendering RJ Barrett, Obi Toppin and Immanuel Quickley plus a ton of draft capital (first-rounders in 2021 and 2023 with pick swaps in 2022 and 2024). Those three players make $16 million, while Lillard makes $39 million. That deal would take the Trail Blazers under the luxury tax threshold and Lillard's deal could be absorbed by the Knicks who should have more than $50 million in cap space this offseason.
Surrounding their new star with quality players would get complicated because the Knicks have nine players with cap holds this summer. But if you pair Damian Lillard with a budding star in Julius Randle well then baby you got a stew going.
Portland would get a guard who took a leap forward this season (Barrett), a lottery pick who is blocked in New York (Toppin) and a scoring guard who showed a ton of potential as a rookie (Quickley). Plus a ton of draft capital to build for the future.
In the end, Lillard going to New York fits perfectly and there's a reasonable path to make it happen.