It'll be a truly sad day in the NBA if and when Portland Trail Blazers superstar Damian Lillard does officially decide to call it quits and demand a trade. There hasn't been a player more outspoken about his loyalty to the franchise that drafted him in recent memory, and a request like that would no-doubt mean he's arrived at a sad truth. While the Blazers have tried repeatedly to build a contender around Lillard, they only have one Western Conference Finals appearance to show for their efforts since drafting him back in 2012. Still, year after year, Lillard has made it clear he's not going anywhere, and the Blazers will continue to extend him and pay top dollar to keep him happy. However, it's starting to feel more and more inevitable, particularly after last season's first-round loss to the Jamal Murray-less Denver Nuggets, that Lillard's patience will eventually run out. So where could the Blazers get the best return for Lillard while still doing him a solid by sending him to a contender?

1. An obvious solution

Portland Trail Blazers receive: Ben Simmons, Tyrese Maxey, Mattise Thybulle, 2024 first round pick, 2026 first round pick

Philadelphia 76ers receive: Damian Lillard

Ben Simmons wants out of his current situation, and in this hypothetical, so does Lillard. Why not swap them? Obviously, Lillard is the superior player (though Simmons is six years younger), so Philly would have to throw in quite a few assets in addition to Simmons to make a deal worth it for Portland. In Simmons, they'd be getting an All-Defense level player who can push the ball in transition and find shooters with precision. He has his glaring flaws (the Blazers would be going from arguably the least-hesitant shooter in the league to the most hesitant) but he's still young enough to grow past his recent struggles and potentially become Portland's next franchise player. They'd essentially just be spinning their wheels the same way they are now, forming a solid playoff team that isn't quite talented enough to break into the contending class, but this trade would at least give Blazers fans some exciting young pieces to watch.

Lillard would be a perfect fit in Philly, offering the floor-spacing that Simmons never could alongside Joel Embiid. He'd give them a late-game weapon that would solve their deficiencies in the clutch, and would bring a level of maturity to a franchise that seems to love drama above all else. Would they instantly become favorites in the East? Brooklyn and Milwaukee would like a word, but this trade sure would make things interesting.

2. The Nuggets speed up their timeline

Portland Trail Blazers receive: Jamal Murray, Facundo Campazzo

Denver Nuggets receive: Damian Lillard

This trade would break quite a few Nuggets' fans hearts, but it's worth it. While Murray has shown flashes of being an offensive superstar, particularly in the postseason, Lillard is a cut above. Could Murray eventually develop into something close to what Lillard is now? Perhaps, but he's going to be spending much of next season rehabbing his torn ACL. The Nuggets organization has established that they're in contention mode right now, signing Michael Porter Jr. and Aaron Gordon to contract extensions in the offseason. Lillard might not be on the same timeline as the rest of their young core, but when a team has an MVP in his prime, it's well worth it to sacrifice the future for a championship now. Pairing Nikola Jokic with Lillard would create one of the most potent and diverse offenses the league has ever seen.

It would be fascinating to see what Murray would do with his own team in Portland. He'd have to adjust to a rebuilding culture after being part of a contender for so long, but he'd have a chance to put up monster numbers.

3. The Big Apple welcomes their savior

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Portland Trail Blazers receive: RJ Barrett, Immanuel Quickley, Obi Toppin, Mitchell Robinson, Kevin Knox, Alec Burks, 2022 first round pick (via Charlotte Hornets),  2024 first round pick, 2026 first round pick

New York Knicks receive: Damian Lillard

The incomparable entertainment Lillard brings on a nightly basis deserves to be showcased on the biggest stage in all of basketball. He would be the best player the Knicks have had since Carmelo Anthony, and although he's a west coast guy through and through, Lillard carries a New York-like mean mug that fans would absolutely adore.

Would they be a contender? Maybe not as constructed after the above trade. Lillard, Julius Randle, Evan Fournier, Nerlens Noel and Kemba Walker off the bench (they'd have to figure out what to do with a superfluous Derrick Rose) doesn't exactly scream ‘Eastern Conference Finals,' but it would be the start of something legitimate. A successful, fun Knicks team led by a superstar in Lillard would no doubt attract free agents. Head Coach Tom Thibodeau established a gritty, business-like culture in New York last season, putting the league on notice that the much-maligned franchise must once again be taken seriously. What better way to reinforce that message than by acquiring one of the best players in the league?

For Portland, the return would be sizable, though it's not exactly filled with known quantities. RJ Barrett made a huge leap last season, and he's the most promising of the Knicks' young core, but there's no certainty whatsoever that he'll turn into a franchise-level player. The same goes for the rest of the package, though they each have their own intriguing qualities (Immanuel Quickley's floater is truly a thing of beauty). It would be more of a desperate move than the first two trades, with Portland banking a lot on the Knicks collapsing (probably a safe bet) by 2024 and New York's high draft picks to select their next superstar.