3 Damian Lillard trades if Bucks decide to hit eject on crumbling roster

The Milwaukee Bucks have not won a basketball game in two weeks. They opened their season against a short-handed Sixers team and came away with a comfortable 15-point win before heading out on the road.

Since then … nada. The Bucks lost their next six games, including two winnable contests against the Cleveland Cavaliers. This has led to some difficult questions about how dire the situation is.

At 1-6, with Giannis Antetokounmpo and Khris Middleton out due to injury, there’s no easy answer in sight. The team is devoid of draft assets and has sky-high payroll, meaning the options they have left are limited.

So let's fire up the ol' trade machine! Who doesn't love a blockbuster trade? Damian Lillard is still a name with significant star power in the NBA. He is an elite off-the-dribble shooter and a dynamic offensive weapon that certain teams would love to put in their uniform. Let's explore a world where the Bucks hit the panic button and trade away their superstar point guard.

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What if the Bucks pull the chute and send Damian Lillard out of town?

Constructing a Lillard trade is tricky business. He'll be 35 next offseason and he still has two years and $112 million left on his contract after this season. In addition, the Bucks are over the dreaded second apron, putting a multitude of restrictions on their trade flexibility.

Most significantly, they are unable to package multiple outgoing players in a trade and cannot receive a single cent of salary over what they send out. That leaves them capped at receiving a maximum of $48,787,676 in a Lillard deal. They also do not control any of their own draft picks until 2031, complicating things even further.

If things are truly as bad as they seem, it would be prudent to treat those outgoing draft picks as sunk costs and simply operate in a way that optimizes their future flexibility. Getting their own draft picks back would be nice, but there's no reason to believe that the Nets, Pelicans or Blazers would have any interest in Lillard.

It is also important to note that any Lillard trade would likely be accompanied by other transactions as well, meaning they wouldn't necessarily be stuck counting on only a Lillard package to salvage their present and future.

With Lillard's age and contract, there are only so many teams that might be willing and/or able to acquire him. As great as he's been throughout his career, these things make it difficult to justify parting with an outlandish trade package for him. Nevertheless, we'll do our best to come up with some semi-plausible scenarios here.

3. Los Angeles Lakers

Come on, we can't speculate about star-studded trades without the Lakers, can we?

The perpetually star-chasing Lakers will inevitably be at least somewhat involved in any trade talks around an All-Star on the market. The Lakers have looked impressive to start the season (recent loss to Detroit notwithstanding) but still go through dry spells on the offensive end on occasion.

More specifically, they are 29th in the league in 3-point attempt rate, which is the single lowest-hanging fruit they could address when the ball is in their possession. Lillard still fires and hits 3s with the best of them and the pressure he could put on the defense in a pick-and-roll with Anthony Davis would be tough to deal with.

The Lakers are in a precarious cap situation, sitting barely under the first apron and unable to add salary in a trade. They'll have to package a number of players to acquire Lillard, but the star power and shooting boost may be worth it.

This is a difficult task, but we'll do our best to get Dame to Hollywood.

As will be a common theme for this exercise, this deal would have to wait until trade restrictions on Bassey and Mamukelashvili are lifted in December. San Antonio plays helper here and earns some second-round picks for their trouble.

This is big and messy. The Lakers give up two starters and a key reserve to add a star for one final push in the twilight of LeBron's career. It might seem strange to upset the apple cart after a good start to the season, but guys like Russell and Hachimura have shown that while they're useful regular season players, they're less impactful in the playoffs when things tighten up.

Depending on how Head Coach JJ Redick wants to mix and match, the Lakers could end up with a youngster like Dalton Knecht or Max Christie in the starting lineup in this reality. This would suddenly have the Lakers sporting high-level shooting from multiple places, a far cry from what their starting five currently does. Alternatively, he might opt for the defensive prowess of Jarred Vanderbilt once he returns from injury.

It's a tough price to pay when you include first-round picks that will convey at a time when neither James nor Lillard are under contract, making it quite risky. This is what "all in" looks like, though, so they may just have to grin and bear it.

For Milwaukee, this breaks Lillard's salary up into more manageable contracts that keep their books much cleaner moving forward. These guys could help them stay somewhat competitive on the floor or net additional assets in follow-up deals, particularly in the case of Russell and Hachimura. It's not the sexiest of packages but Lillard's trade value is only so high. That first-round picks are the real prize.

2. Miami Heat

Lillard spent a significant amount of time last summer not-so-privately lobbying to get to South Beach but ultimately failed to make it happen. The Miami Heat have long been rumored to be in the market for Lillard and could be in a position to finally make it a reality.

Like the Lakers, the Heat are over the first apron, making trade scenarios more complicated. With Miami and Milwaukee unable to take on additional salary in trade, a third team who can add salary in a trade needs to be recruited.

The Heat have been struggling to put the ball in the basket for the last several seasons. With Jimmy Butler and Bam Adebayo providing a defensive infrastructure, Lillard could easily slide in to provide the high-level shot making they have been missing. Then again, we all thought the same thing about his fit with the Bucks, didn't we?

We don't deal in skepticism with the trade machine, though. How do we get Lillard to Miami?

Seth Curry and Thomas Bryant have trade restrictions, so this deal would need to occur later in the season. The Hornets have already shown a willingness to help facilitate big trades, so they're chosen as the third participant in this deal.

This becomes a pick-centric package for the Bucks, attempting to recoup some draft capital after having depleted their own stores throughout the years. The Heat tend to stay away from the absolute bottom of the standings, but picks that are five and seven years out will always have the chance to be juicy.

There isn't a ton of immediate salary relief for Milwaukee here but both Rozier and Robinson are set to expire before Lillard would. Both are exceptional shooters that could do some damage alongside Antetokounmpo's gravity if they wanted to see how some tweaks might work out as well. More likely, one or both could be moved to another team to extract some additional value.

For the Heat, the appeal is pretty easy to see. Giving up those picks could turn out poorly when they convey, but they need to give up some value. Lillard, Butler and Adebayo is a top three that makes a lot of sense. They would be flanked by depth pieces in Tyler Herro, Nikola Jovic, Haywood Highsmith, Jaime Jaquez Jr. and Kevin Love to round out the rotation.

Herro is an imperfect residual fit in this scenario, though this is true even now. Adding a win-now piece like Lillard at such a price might spur more urgent action to turn Herro into some role players that fit better around their stars if they can.

The Heat have refused to raise their team salary above the second apron, so they'll have to continue to be creative with their books and unearth diamonds in the rough to add to their rotation. This would include filling multiple roster spots while staying under that apron after having sent so many players out in trade. But if there's any team that can cobble together a workable rotation and defense with limited resources, it's the Heat.

1. Orlando Magic

The Orlando Magic are a team on the rise with a stifling defense and a need for offensive firepower. After losing Paolo Banchero to a torn oblique for at least the next month, they will be even further behind the eight ball on that end of the floor.

But paired with a deep ball threat like Lillard, Banchero could be operating with space he has not seen in his NBA career upon his return. Lillard is not exactly on the same point of the age curve as the rest of their roster, but the Magic are a rare young team who might be able to make real noise with the right veteran addition.

They did just give big extensions to Franz Wagner and Jalen Suggs, with Banchero set to follow suit next summer. But with only two more years on Lillard's contract after this season, they just might be able to squeeze it in. Suggs' salary descends over time, as does that of Jonathan Isaac. The Magic also have flexibility in reducing money paid to players like Isaac, Mo Wagner and Cole Anthony through non-guarantees and Team Options.

Let's see what we can come up with for these partners.

For this one, any deal involving Kentavious Caldwell-Pope would not be legal until he becomes trade-eligible in the middle of December.

The nice thing for these two teams is that the Magic have a few different ways they could put a package together for Lillard. In this scenario, the Bucks get a recent lottery pick in Anthony Black, who has already shown signs of becoming an impactful defender before turning 21. He is still learning how to navigate the offensive end (to put it nicely), but he's quite young and has intriguing raw tools.

Caldwell-Pope is necessary salary filler here. The versatility of Jalen Suggs allows him to move off the ball to accommodate Lillard while continuing to hound ball handlers on defense in the wake of KCP's departure. Depending on how drastically they want to remake their roster, the Bucks could certainly use the perimeter defense he provides, even if his shooting has been cold to start the year. Alternatively, there would be no shortage of teams willing to give up assets if they wanted to re-route him elsewhere.

This trade would cut the Bucks' payroll by a few million dollars, saving on raw payroll and a significant amount more in luxury tax payments as well. As alluded to earlier, Mo Wagner's contract comes with a Team Option for next year, allowing the Bucks to immediately shave another $11 million off their books at that point. As with Caldwell-Pope, he might also fetch some value in a trade if they chose to go that route.

The books for the Magic would get a little hairy moving forward, particularly in 2026-27 when a Banchero extension would kick in. But the cap continues to rise and hey, Lillard has a Player Option for that year, so perhaps he'd be willing to opt out and re-sign for a number that is easier to stomach.

There are other iterations that could involve some combination of Cole Anthony, Jett Howard, Gary Harris and Goga Bitadze as well. If the Magic are ready to take a step forward at a cost that won't sink them, they could be an ideal landing spot for Dame Dolla.