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Damian Lillard, who has seemingly been in the rumor mill since the onset of the industrial revolution, has finally requested a trade from the Portland Trail Blazers. After years of speculation and ping pong balls, one of the NBA's best guards is expected to find a new home in the coming days or weeks, and he reportedly has his heart set on one team in particular: the Eastern Conference champion Miami Heat.

We know how this usually goes. When a star wants to go to one team in particular, he usually gets there. But Lillard seemingly has a far more robust market, and plenty of teams could talk themselves into championship contention with him at the helm. So let's take a look at the Lillard sweepstakes. What could the Heat give up to land Lillard, and who has the assets and upside to take Lillard away from his favored destination?

Miami Heat

There are a couple of core problems with Miami's presumed offer:

  • Miami currently owes a 2025 first-round pick to Oklahoma City that simultaneously encumbers all of their first-round picks between 2024-2027 due to a combination of protections and the Stepien Rule. That means, for the time being, the Heat are limited to just two tradable first-round picks.
  • Miami's only positive-value matching salary is Tyler Herro. The Blazers already have Scoot Henderson, Shaedon Sharpe and Anfernee Simons in their backcourt. They likely aren't interested in adding an expensive young guard.

There's a simple workaround to that first problem. The Heat and Thunder have a very strong trading relationship, and they've already adjusted the protections on that pick once before. If both sides agreed to simply making that pick an unprotected 2026 selection, the Heat would then be able to give away three first-round picks: 2024, 2028 and 2030, along with swap rights in 2025, 2027 and 2029. That's probably not the trade package Portland would prefer, but it's something.

The Herro problem is a bit harder to solve. The Heat and Blazers would need a third team, and finding a fit for Herro isn't especially easy. Very few teams are so thin at guard that they'd want to make a nine-figure commitment to Herro. Would Brooklyn do so with Spencer Dinwiddie's expiring contract and a first-round pick of their own? They'd likely need to shed some more money for luxury tax purposes. How about Utah? The Jazz need a primary ball-handler and have no shortage of assets. There are possibilities here, but it's not clear how many.

From there, Miami has a few potentially interesting trade sweeteners. Kyle Lowry's expiring deal might hold some value to Portland as a mentor to their young guards. Nikola Jovic and Jaime Jaquez make sense as front-court projects. There's a viable deal here even if the Blazers could probably do better elsewhere.

Brooklyn Nets

In an open bidding war, Miami would have no chance against Brooklyn. The Nets control Phoenix's first-round picks in 2025, 2027 and 2029. They have future picks from Dallas and Philadelphia as well, with that Dallas pick also unprotected. Oh, and starting in 2028, they control their own first-round picks again. Not only does that package include a high volume of picks, but those picks come from diverse sources as well. Portland would just need to hope that one of the Nets, Suns, Mavericks and 76ers flame out and they'd wind up with valuable assets. If several of those teams do? The Blazers would be looking at a haul.

Brooklyn could match salary with mostly expiring contracts (Spencer Dinwiddie, Patty Mills and Royce O'Neale). They could also potentially send out Ben Simmons if that's a project Portland is willing to take on. The idea for Brooklyn would be to retain Mikal Bridges, Dorian Finney-Smith, Cam Johnson and Nic Claxton as a starting lineup to put around Lillard. Beyond that core group, they would likely be flexible.

Of course, it's also worth asking if the Nets are ready to jump right back into the deep end with another superstar trade so quickly after their disastrous Kyrie Irving, Kevin Durant and James Harden experiment. Brooklyn might prefer to wait and use those assets on someone a bit younger. They might prefer to simply build organically. The Nets can make a real run at Lillard if they want to. Whether or not they choose to do so comes down to their priorities.

Philadelphia 76ers

Only two days ago, the 76ers were on the wrong side of a superstar trade request when James Harden picked up his player option with the expectation that he would be moved. There were plenty of rumblings that Philadelphia wouldn't trade Harden to his preferred destination (the Clippers) for an underwhelming smattering of picks and veterans. No, Daryl Morey is a big-game hunter, and now, Lillard is in his sights.

Here is, essentially, the idea: Philadelphia would send Harden to the Clippers for some combination of their unprotected picks in 2028 and 2030, unprotected swaps in 2027 and 2029, promising youngster Terance Mann and a few of their expensive wings. They would then turn around and reroute some or all of those assets, along with their own ascending young guard in Tyrese Maxey, out to Portland in a package for Lillard. Now, this is where things get even harder. As we covered with Herro, the Blazers likely don't want another young guard. Therefore, we'd probably need a fourth team to make this work.

That's doable. Maxey should generate plenty of interest. Would the Raptors give up OG Anunoby for him now that they've lost Fred VanVleet? How about a Chicago package of Patrick Williams and picks? Utah, Brooklyn and San Antonio all make sense for Maxey as well. Finding him a home would not be difficult. The real question here is how interested Lillard would be in a partnership with reigning MVP Joel Embiid. For now, his heart is set on Miami. We've seen players change their minds during the process of getting traded. Philadelphia will likely have a chance to woo Lillard. With Harden exiting, they can generate the assets to go get him. 

San Antonio Spurs

Here's the reported wild card in these discussions. ESPN's Ramona Shelburne reported that Lillard has a "deep respect" for the Spurs organization. Victor Wembanyama could help Lillard contend until he retires. The Spurs still have the cap space to go sign Brook Lopez as their starting center. They own future picks from the Bulls and Hawks from their previous trades of DeMar DeRozan and Dejounte Murray, respectively. Throw in their own future picks and the Spurs are among the most flexible teams on the trade market moving forward.

Here's the question: are the Spurs ready to go all-in right now, before they've even seen Wembanyama play? Remember, if he's as good as the basketball world expects him to be, he'll be able to recruit just about anyone to serve as his co-star. The Spurs could get someone younger. They could get someone at another position if they'd prefer. If the Spurs grab Lillard right now, they'd be sacrificing years of opportunities elsewhere. That's not a sacrifice to be undertaken lightly. San Antonio can get into the mix if it wants to, but it's up to them to decide if doing so would be worthwhile.

Toronto Raptors

Let's throw out a stealth contender for Lillard's services. The Raptors just lost VanVleet for nothing and are seemingly directionless. They've made unexpected blockbusters in the past, with Kawhi Leonard winning them a championship in 2019. They control most of their future draft capital. A Scottie Barnes offer likely gets a deal done right now, but if Toronto wasn't going to do that for Kevin Durant, it likely wouldn't for Lillard either. More likely, a package would be built around picks and either Pascal Siakam (presumably headed to a third team) or OG Anunoby.

Could a Raptors team built around Lillard, whatever remains at forward and role players like Gary Trent Jr., Jakob Poeltl and Dennis Schroder win the East? Possibly. If nothing else, the Raptors wouldn't be the sort of super team Lillard reportedly prefers to avoid. But convincing him to come north would not be easy. Toronto couldn't convince Leonard to stay longer than a year. As interesting as this possibility would be on the court, the off-court reality makes it relatively unlikely.