A Wild 3-Team Trade to Land Draymond Green with Damian Lillard

Damian Lillard has been a fixture in the NBA's rumor mill for years. This summer, Draymond Green is an unrestricted free agent. And last week, Sam Amick of The Athletic reported Lillard has an eye for his Western Conference rival.

That and plenty of other buzz has led to chatter about a potential pairing of the two stars. And it got us thinking about how that might actually happen.

The Portland Trail Blazers don't figure to have cap space this summer, so Green would have to go in a sign-and-trade. Most importantly to this equation, Green would have to make it clear he is ready to move on from the Warriors. It's not a position the team expects or hopes to be in after dealing Jordan Poole for Chris Paul, but if it ends up the reality, Golden State could have a trade partner in Portland.

The question is, would that be enough to finally give Lillard a contender? Or is there another team—a third team—out there that might unload a star or near-star to get younger and bring it all together?

Let's get wild and check it out.

The Trade

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Draymond Green and Damian Lillard

Before we get into the specific justifications for each of the teams involved, let's look at the entire three-teamer at a glance.

Portland Trail Blazers Receive: Draymond Green (via sign-and-trade for a three-year contract starting around $27 million) and DeMar DeRozan

Golden State Warriors Receive: Jusuf Nurkić, Patrick Williams, Shaedon Sharpe and an unprotected 2026 first-round pick from Portland

Chicago Bulls Receive: Anfernee Simons, Jonathan Kuminga and an unprotected 2030 first-round pick from Portland

One note on the picks before we proceed. Because the Blazers already owe a first to the Bulls that rolls over from year to year whenever Portland is in the lottery, sending more first-rounders out is tricky. That is, unless, both of those teams agree to an adjustment on those protections.

In this package, Chicago would theoretically be agreeing to an unprotected pick in 2030, rather than waiting year after year for the possibility of conveyance.

Not sold yet on everything else? Let's explore why this works for everyone.

Portland Goes More Than All-in

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Damian Lillard

Portland Trail Blazers Receive: Draymond Green (via sign-and-trade for a three-year contract starting around $27 million) and DeMar DeRozan

Portland Trail Blazers Lose: Anfernee Simons, Jusuf Nurkić, Shaedon Sharpe, an unprotected 2026 first-round pick and a lottery-protected 2030 first-round pick

On the surface, this almost seems like a no-brainer for the Blazers. Plugging Draymond and DeRozan into a rotation that still includes Lillard would probably make them a lock to finish top 10 in the West. Not giving up Scoot Henderson would be a huge win too (though it might make this a non-starter for Golden State).

But this isn't as obvious as that. Lillard turns 33 in July. DeRozan turns 34 in August. Green is 33. There's no guaranteeing that trio opens up a title window for Portland, and even if it did, it wouldn't be open long.

But there's no doubt this deal makes the Blazers better in the short term.

They're dead last in points allowed per 100 possessions over the last three seasons, and Green is a transformative defender. He wouldn't fix that unit overnight, but his versatility and leadership on that end would go a long way.

And with the kind of attention that Lillard commands outside the three-point line, DeRozan would be able to take advantage of holes in the mid-range.

Would all of that bump Portland up to the Denver Nuggets' tier in the West? Probably not, but it would at least get him closer to the "chance" he's been after.

Golden State Breaks Up the Dynasty Core

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Draymond Green, Klay Thompson and Stephen Curry

Golden State Warriors Receive: Jusuf Nurkić, Patrick Williams, Shaedon Sharpe and an unprotected 2026 first-round pick from Portland

Golden State Warriors Lose: Draymond Green and Jonathan Kuminga

This is probably the hardest sell of the exercise.

Draymond has four championships with the Warriors, who just acquired Chris Paul and appear ready and willing to spend a fortune to chase another title.

It still feels like the likeliest outcome of Green's free agency is that he'll re-sign with Golden State.

BUT if he tells the Warriors he's not coming back and that he wants to play with Lillard (a lot of hypothetical leaps happening here, I know), the Blazers might have some things to coax Golden State into a sign-and-trade.

The Warriors needed more size down the stretch in 2022-23. Kevon Looney's shoulders are wide, but there was simply too much responsibility on them. Whether as a starter or reserve, Nurkić would take some of that from Looney, while also adding some shooting from the 5 (he's hit 34.1 percent of his threes over the last three seasons).

He also costs a lot less than Green figures to, with a salary that doesn't exceed $20 million in any of his three remaining seasons.

Williams, meanwhile, may not have the upside of Kuminga, but he's still just 21 years old and has a career 41.4 three-point percentage. Outside shooting is a more adaptable skill than Kuminga's athleticism, especially in the Warriors system.

The biggest prizes for Golden State, though, are Sharpe and the 2026 pick.

Blazers fans may think that's too much to give up for two stars (or former stars) in their mid-30s, but the Warriors aren't going to surrender Green (or be part of a sign-and-trade) without a hefty return.

The organization's failure to develop James Wiseman (and to varying degrees Kuminga, Poole and Moses Moody) may make some wary of continuing to straddle the line between "win now" and "develop for the future," but Sharpe is the kind of prospect who can alleviate that wariness.

The high-flying, 6'6" wing didn't total many rebounds, assists, steals or blocks as a rookie, but his athleticism and 36.0 three-point percentage are enticing.

Chicago Turns Back the Timeline

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DeMar DeRozan and Anfernee Simons

Chicago Bulls Receive: Anfernee Simons, Jonathan Kuminga and a lottery-protected 2030 first-round pick from Portland

Chicago Bulls Lose: DeMar DeRozan and Patrick Williams

News of a three-year extension for center Nikola Vučević makes a shakeup for the Bulls feel a lot less likely than it did a few days ago, but this move still makes some sense for Chicago.

For one thing, Simons is almost 10 years younger than DeRozan. And for a team that finished 29th in threes per game in 2022-23 (and 16th in three-point percentage), the addition of Simons' high-volume (and highly accurate) outside shooting has to be intriguing.

He may not be a point guard, but he's still young enough to potentially be molded into that too. And with Lonzo Ball's health still a massive concern (and mystery), the Bulls should be in the market for help at that position.

The Williams-for-Kuminga aspect of this deal isn't quite as easy to explain, but the latter is about a year younger. And Chicago, which isn't as close to title contention as the Warriors, can justify the extra development Kuminga may need a bit easier.