Damian Lillard watched Scoot Henderson walk across the NBA Draft stage and don a Blazers cap in late June. That was the last straw. He requested a trade days later, seeking to end his 11-year partnership with the franchise and city that embraced him as a top-10 pick out of unheralded Weber State back in 2012.

The 33-year-old named one destination on his wishlist: the Miami Heat. He loudly broadcast, through intermediary channels, that he would only suit up for the Heat, and that any other franchise would be acquiring an unhappy superstar.

While the league has since cracked down on the public nature of Lillard's trade demands, that hasn't stopped reports of him potentially requesting another trade to Miami if he ends up in Toronto, for example. It also hasn't stopped several alternate suitors from emerging in the marketplace, with the Blazers keen on forcing the best offer out of a Heat team reluctant to part with all its assets.

If Miami remains too stubborn to pony up and the Blazers make a concerted effort to get a deal done before camp starts on Oct. 3... then it becomes exceedingly possible — maybe even likely — that Lillard ends up somewhere he doesn't want to be. We can only guess what might happen then, but the Toronto Raptors, Chicago Bulls, and Philadelphia 76ers are all on the radar along with Miami.

All four teams have the assets to get Portland on the phone. Here's what it would take from each team to get a deal across the finish line.

NBA Rumors: Potential Blazers-Raptors trade for Damian Lillard

It is past time for the Raptors to simply embrace a rebuild... but, Damian Lillard is a singular talent. We have seen trading for a disgruntled star work in Toronto's favor before. Pascal Siakam has been mentioned as a trade candidate all summer, but every sign points to him wanting to re-sign. Maybe the Raptors commit to half a decade of Lillard, Siakam, and Scottie Barnes.

Can that team realistically compete for a championship? Their chances are dubious at best, but all it takes is a stroke of luck and a favorable side of the bracket. Lillard is at the tail end of his prime, but he's coming off the best individual season of his career. The Raptors' core areas of weakness are poor 3-point shooting and a lack of perimeter creators. Lillard addresses both, all while giving new head coach Darko Rajaković — known for his offensive innovation — a once-in-a-generation point guard to build his system around.

Pascal Siakam is a deadly slasher who has improved the ancillary aspects of his skill set in recent years. He was a bonafide All-Star and All-NBA candidate last season and he would probably be the best co-star of Lillard's career since LaMarcus Aldridge. Their games are very complementary.

Meanwhile, Scottie Barnes would get to hone his talents as a play-connector in an offense with actual spacing and movement. His numbers may not improve, but his impact on winning very well could. Plus, he's an elite wing defender. Lillard has never been blessed with a defensive core as well-rounded as Barnes, Siakam, and Jakob Poeltl.

Lillard can push away the Raptors all he wants... but this would be a very good fit on the court. Maybe he has a better shot at the Larry O'Brien in Miami, but the Raptors would not be dooming him to irrelevancy.

NBA Rumors: Potential Blazers-Bulls trade for Damian Lillard

The Chicago Bulls are completely directionless, clinging onto a failed core with no real hope of contending. This is easily the most depressing outcome for a hypothetical Lillard trade; he should be fighting tooth and nail to avoid Chicago sports purgatory.

Still, Lillard is enough of a game-changer for the Bulls to talk themselves into a trade. There's no way financially for both DeMar DeRozan and Zach LaVine to survive a deal; in this instance, DeRozan heads to Portland with an understanding that the Blazers will rope in a third team eager for veteran assistance. DeRozan's trade value is suspect, but he's coming off back-to-back All-Star nods. He can still help a team win, even if it's fair to wonder how adaptable his skill set is.

The Blazers' real prize here is the cache of draft capital from a Bulls team destined to flunk the Lillard-LaVine experiment. Patrick Williams doesn't get much shine for a recent No. 4 overall pick, but he has turned into a high-level wing defender with a bankable 3-point shot and some mid-range juice. He would form a solid defensive backbone in tandem with Jerami Grant.

Lillard and LaVine would stretch defenses thin and give the Bulls' offense genuine oomph. LaVine is a slippery driver who regularly pressures the rim and he can help ease Lillard's creation burden as the point guard ages. Nikola Vucevic is a skilled offensive big who can dominate mismatches in the post or run two-man actions with Lillard on the perimeter. There's decent connective tissue in place — Alex Caruso, Ayo Dosunmu, Coby White, and Jevon Carter can all play, but they're also all guards.

Chicago would need to swing another trade to bolster its wing depth, which gets tricky. The ideal pathway here is to not include Williams — or perhaps to center the trade on LaVine instead — but there's no way for the Bulls to trade for Lillard while maintaining credible frontcourt depth and fielding a quality defense. Billy Donovan is a defensive whiz who can tease competence out of the most improbable of lineups, but this would be a whole new challenge for him.

NBA Rumors: Potential Blazers-76ers trade for Damian Lillard

The Philadelphia 76ers are eager to keep their sinking ship afloat. The James Harden... saga... is still unfolding, so why not add another potentially unhappy point guard to the mix? Kyle Neubeck of PHLY reports that the Sixers have talked to Portland multiple times this offseason. The only logical way for Philadelphia to acquire Lillard is to trade Tyrese Maxey, which is a risk — but, potentially one worth taking. Also of note, Philadelphia has not signed Maxey to the customary five-year extension most valuable young players sign before hitting restricted free agency. So, Daryl Morey has kept his options open.

Damian Lillard is a bonafide superstar. Lost amid the drama around his trade request and the constant worrying about his hefty contract is the fact that Lillard averaged 32.2 points and 7.3 assists on 64.5 TS% last season. He would immediately improve the Sixers' title odds in a winnable East. He's one of the best volume shooters in NBA history. Joel Embiid has always been most successful when paired with unabashed gunners. It's a perfect marriage.

This trade also allows the Sixers to keep Harden in the mix. Harden has loudly broadcast his desire to leave Philly, but he's 34 years old with one year left on his contract and zero interested suitors. At some point he will have to admit defeat. Plus, it has to be mighty tempting to play next to Embiid and Lillard for a coach who is not Doc Rivers. The Sixers fired Rivers in the first place to appease Harden and it's clear Morey is willing to get uncomfortable if there's any chance of convincing Harden to stick around (or at least play up his trade value a bit before the deadline).

It would be hard not to register this trade as a desperation move from the Sixers. Joel Embiid has left the door wide open for a potential departure and Maxey is that roster's only semblance of an investment in the future. Sending him to Portland all but confirms 2023-24 as a win-or-bust season, but that has been the case for years now. The Sixers are in a race against time to win before Embiid ages out of his prime or asks for a trade. Lillard boosts their immediate odds considerably.

The Blazers have too many guards, but Maxey is good enough to warrant the talent-over-fit investment at the beginning of a rebuild. The outcome would probably be an Anfernee Simons trade somewhere down the line, but Maxey's volume shooting and speedy transition play would fit naturally next to Scoot Henderson in the Portland backcourt. Tobias Harris makes the money work and he's a good vet to have in the locker room for a year.

NBA Rumors: Potential Blazers-Heat trade for Damian Lillard

The Miami Heat cannot be ruled out, no matter how dead those conversations appear from the outcome. Lillard has done everything in his power to position Miami as the favorites and the Heat's competitive window is preciously narrow with Jimmy Butler entering his age-34 season. Miami can always attract stars in free agency, but it's still not often that players of Lillard's caliber come knocking.

Lillard would cement the reigning East champs as favorites in a winnable conference. Lillard would improve the Heat's core area of weakness (in the regular season), which was consistency beyond the arc. He's a high-volume shooter who can split playmaking duties with Butler, who operates almost exclusively within 18 feet of the basket during the regular season.

The Heat take Jusuf Nurkic's contract off Portland's hands to sweeten to pot in lieu of better prospects or draft capital. The Heat don't have a young player on the level of Tyrese Maxey or O.G. Anunoby, but Tyler Herro is a proven 20 points per game scorer who can yield more assets from the Utah Jazz or another interested third team.

Jaime Jaquez Jr. and Nikola Jovic are first-round picks with varying degrees of upside. Jaquez in particular doesn't really fit with Portland's core, but he's a young player to develop in a patient rebuild. There's no harm in taking as many swings as possible if you're the Blazers front office; the goal is the bleed Miami's asset collection dry.

This framework allows Miami to keep Caleb Martin on the heels of his postseason breakout. A starting five of Bam Adebayo, Caleb Martin, Jimmy Butler, Damian Lillard, and *insert fifth player here* is hard to deny. There's definite risk in giving up as much as the Heat are here, but it's all relative. The Heat simply lack the trade flexibility of other interested parties. This isn't the best deal, but it's enough for Portland to walk away satisfied.