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PORTLAND, OREGON - APRIL 09: Damian Lillard #0 of the Portland Trail Blazers looks on during the third quarter against the Golden State Warriors at Moda Center on April 09, 2023 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Steph Chambers/Getty Images)
PORTLAND, OREGON - APRIL 09: Damian Lillard #0 of the Portland Trail Blazers looks on during the third quarter against the Golden State Warriors at Moda Center on April 09, 2023 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Steph Chambers/Getty Images)Steph Chambers/Getty Images

A New Damian Lillard 4-Team Trade Where Everybody Wins

Andy BaileyAug 3, 2023

We're now a month removed from Damian Lillard's trade request, and he's still a member of the Portland Trail Blazers. But there's plenty of time for a deal to get done between now and training camp, and the whole situation feels a little less comfortable with each passing day.

The holdup to this point may be the Blazers' hesitance to take on Tyler Herro's contract. The idea of rerouting Herro elsewhere has had plenty of people contemplating three-team deals.

But what if we got a little wilder?

Imagine with us a four-team scenario that involves another discontented star and finally gets Dame to Miami.

The Deal

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Damian Lillard and James Harden
Damian Lillard and James Harden

Before we get into why each team would entertain the madness below, it helps to see the entire deal at a glance.

So, *deep breath*, here you go...

Portland Trail Blazers Receive: James Harden's expiring contract (can be flipped later), Kyle Lowry's expiring contract, Jaime Jacquez, Nikola Jović, a 2028 first-round pick from Miami, a 2030 first-round pick from Miami and a 2030 second-round pick from Chicago

Miami Heat Receive: Damian Lillard, Jusuf Nurkić, a 2029 second-round pick from Philadelphia and a 2028 second-round pick from Chicago

Philadelphia 76ers Receive: Zach LaVine, Tyler Herro and a 2029 second-round pick from Portland

Chicago Bulls Receive: Tobias Harris' expiring contract, Caleb Martin, Keon Johnson, a 2029 first-round pick swap with the 76ers and a 2030 first-round pick from Philadelphia

After you've had a chance to digest all of the above, dive into the justifications for each team and feel free to quibble over the number of picks and young talent involved. There's usually room for haggling.

Portland Tips Off the New Era

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LAS VEGAS, NEVADA - JULY 09: Scoot Henderson #00 of the Portland Trail Blazers looks on as the team warms up for a 2023 NBA Summer League game against the San Antonio Spurs at the Thomas & Mack Center on July 09, 2023 in Las Vegas, Nevada. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Ethan Miller/Getty Images)
LAS VEGAS, NEVADA - JULY 09: Scoot Henderson #00 of the Portland Trail Blazers looks on as the team warms up for a 2023 NBA Summer League game against the San Antonio Spurs at the Thomas & Mack Center on July 09, 2023 in Las Vegas, Nevada. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Ethan Miller/Getty Images)

Portland Trail Blazers Receive: James Harden's expiring contract (can be flipped later), Kyle Lowry's expiring contract, Jaime Jacquez, Nikola Jović, a 2028 first-round pick from Miami, a 2030 first-round pick from Miami and a 2030 second-round pick from Chicago

Portland Trail Blazers Lose: Damian Lillard, Jusuf Nurkić, Keon Johnson and a 2029 second-round pick

Blazers fans might want more for Lillard, but Heat fans won't want to give up this much. Therefore, this feels like a happy medium.

Portland would immediately get cap flexibility in 2024, a one-year mentor for Scoot Henderson in Lowry, multiple young talents who can potentially develop alongside Scoot, multiple picks and one wild card in Harden.

If the Blazers are out on acquiring Tyler Herro in a Lillard deal, they probably wouldn't want Harden taking developmental reps from Scoot, either. But the Blazers should be more open to the Los Angeles Clippers' potential offer for Harden than the Philadelphia 76ers are.

Sixers president Daryl Morey recently said he won't make a Harden deal unless it gets them a player who'll help them chase a title or a package that can be flipped for such a player. There's no such source of (or need for) pickiness with Portland. So, the Blazers' side of this deal could swell even more after flipping Harden.

Another obvious benefit here is shedding the last three years and $54.4 million left on Jusuf Nurkić's contract.

The end of an era is a tough thing to accept, especially when your star is 33 years old, under contract through 2026-27 (when he'll be 36) and set to make $63.2 million that season. Lillard's value on the trade market is out of his hands.

But even if this deal doesn't land the Blazers quite the king's ransom that the Utah Jazz got for Rudy Gobert (an outlier that shouldn't be compared to other trades) or the Brooklyn Nets got for Kevin Durant, the final roster is more than intriguing.

Portland would walk away with cap flexibility, Henderson, Shaedon Sharpe, Kris Murray, Jaime Jacquez, Nikola Jović, whatever it gets for Harden and a bigger war chest of future picks.

Miami Goes All-In on This Era

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Jimmy Butler and Damian Lillard
Jimmy Butler and Damian Lillard

Miami Heat Receive: Damian Lillard, Jusuf Nurkić, a 2029 second-round pick from Philadelphia and a 2028 second-round pick from Chicago

Miami Heat Lose: Tyler Herro, Kyle Lowry, Caleb Martin, Jaime Jacquez, Nikola Jović, a 2028 first-round pick and a 2030 first-round pick

Heat fans are largely convinced that their best offer for Lillard is better than anyone is giving it credit for. Nearly everyone else is seemingly convinced it's an affront to the league and Lillard's talent.

Again, the reality of the situation probably lies somewhere in the middle of those extremes. This exchange hopefully represents that middle.

A Lillard trade unquestionably makes the Heat better in the short term. He seems like an ideal fit alongside Jimmy Butler and Bam Adebayo, and his outside shooting will make their lives significantly easier.

If Lillard does eventually land in Miami, the Heat should immediately be considered a Tier 1 contender. They just made the NBA Finals with an undrafted, 6'3" below-average shooter with a career scoring average of 7.7 points. Plugging Lillard into Gabe Vincent's spot would be a monumental upgrade.

But the Heat aren't going to get him without a major sacrifice. This deal mostly clears the roster of interesting young talent and hampers their ability to eventually rebuild through the draft or make future trades that would require picks.

Miami might be the one team that's close enough to a title and possesses the right assets to make this happen. It can justify taking on a contract that could be nightmarish by its last few seasons because it can win a championship in the next year or two.

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Philadelphia Gets More Explosive

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Tyler Herro and Zach LaVine
Tyler Herro and Zach LaVine

Philadelphia 76ers Receive: Zach LaVine, Tyler Herro and a 2029 second-round pick from Portland

Philadelphia 76ers Lose: James Harden, Tobias Harris, a 2029 first-round pick swap with Chicago, a 2030 first-round pick and a 2029 second-round pick

Based on Daryl Morey's mandate, the Sixers have to feel like they can win it all after any Harden trade. This one could make them more explosive.

Neither LaVine nor Herro will ever be the passer Harden is, but LaVine is six years younger than Harden and Herro is 11 years younger. Both have proven an ability to score 20-plus points per game while chipping in a decent amount of playmaking. Both are more consistent three-point shooters than Harden, too.

While they may not facilitate quite as many wide-open looks for Joel Embiid, the attention they'll command on the perimeter will make it harder for opposing defenses to rush Embiid's catches inside the arc.

Morey probably won't want to lose picks in a Harden deal, but if you just look at the net talent-for-talent swap here (LaVine and Herro for Harden and Tobias Harris), it gives Philadelphia a younger and more explosive offense with which to surround Embiid.

The emerging trio won't have the same stench of playoff failure currently hovering over Harden and the reigning MVP, too.

Chicago Starts a Rebuild

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DeMar DeRozan, Nikola Vučević and Zach LaVine
DeMar DeRozan, Nikola Vučević and Zach LaVine

Chicago Bulls Receive: Tobias Harris' expiring contract, Caleb Martin, Keon Johnson, a 2029 first-round pick swap with the 76ers and a 2030 first-round pick from Philadelphia

Chicago Bulls Lose: Zach LaVine, a 2028 second-round pick and a 2030 second-round pick

This is the hardest sell among these teams. You can only entertain it if the Bulls are willing to accept that it's time to rebuild.

The deal doesn't make the Bulls better in the short term, so they'd probably have to be ready to move DeMar DeRozan and Nikola Vučević in separate deals, too.

In that case, Chicago should entertain the chance to turn a pair of second-round picks into a distant first-rounder, shed the last four years and $178.1 million of Zach LaVine's contract and take a flyer on 21-year-old Keon Johnson.

In that scenario, Harris and Martin are little more than salary filler, and Chicago might insist on another pick or young talent from somewhere. But the general idea of tipping off the rebuild is reasonable.

McCollum's Dagger Sinks Knicks 🔪

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