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Grade the trades: 3-team ideas to get Damian Lillard from Blazers to Heat

Andrew Hanlon
Andrew Hanlon

Rip City Project

Damian Lillard, Portland Trail Blazers (Photo by Soobum Im/Getty Images)

The NBA world flipped upside down, or at least the 2023 offseason did, when Damian Lillard asked the Portland Trail Blazers for a trade on July 1.

Shortly after, Shams Charania of The Athletic reported that Lillard’s preferred destination was the Miami Heat.

The problem, however, is that Miami has less to offer Portland than just about any NBA team that would entertain the idea of bringing Dame aboard. To make matters more difficult for the Heat, the Blazers reportedly have little interest in Tyler Herro, Miami’s 23-year-old guard and the 2022 NBA Sixth Man of the Year who would be the logical centerpiece of any trade.

Herro’s redundancy with Portland’s current crop of guards and the fact that he’s about to enter the first year of a four-year, $120 million deal makes him unattractive to Rip City. The Blazers already have Anfernee Simons to play the role Herro would fill as a scorer and secondary playmaker, except Simons has put up better numbers thus far in his career, is on a more team-friendly contract, and is only a year older.

A Damian Lillard trade to the Miami Heat would require a third team

This would necessitate at least one more team to join the deal, almost certainly as a landing spot for Herro.

Disclaimer: Finding such a trade is not easy.

Any franchise that would bring Herro aboard must be in need of a scorer and playmaker in the backcourt. Herro is 6-foot-5 with legitimate combo-guard skills and, again, is only 23 years old.

Yes, he’s about to kick off an expensive four-year contract, but for a player of Herro’s caliber, it’s not an exorbitant, cap-killing deal. His abilities as a player are already becoming undervalued simply because Portland doesn’t have use for him as it leans into a rebuild around young guards in Simons, Scoot Henderson, and Shaedon Sharpe.

Which teams are looking for a player like Herro and would be willing to jump into a Blazers-Heat deal for Lillard as the savior of a potential league-altering trade?

Here are a pair of three-team ideas that could get Lillard to his preferred landing spot, the Blazers a fair package in exchange for one of the best players in the league, and a third team in need of a player of Herro’s caliber the right compensation for taking the young guard and his long-term contract.

The Toronto Raptors could be a landing spot for Tyler Herro in a three-team Damian Lillard trade with the Heat.
Gary Trent Jr. (center), Toronto Raptors (Photo by Cole Burston/Getty Images)

Three-team trade No. 1: Lillard to the Heat, Herro to the Toronto Raptors

This trade isn’t the most ideal scenario for the Blazers, but it gets the franchise’s most beloved player where he wants to go and the Raptors get a backcourt player who can score and run the show at times after the loss of Fred VanVleet to the Houston Rockets.

Toronto re-signed guard Gary Trent Jr. and added Dennis Schroder in free agency, but Herro brings a different element to a team holding onto OG Anunoby and Pascal Siakam, assumedly with the intention to remain a competitor in the Eastern Conference. For their troubles, the Raptors unload three contracts and pick up two additional second-round picks.

Miami gets Lillard; that part of the deal is self-explanatory.

Now, for why the Blazers would be interested in making this trade:

  • Young and Porter Jr. are on expiring contracts. Portland would clear more than $14 million in cap space after this season.
  • Jovic and Jaquez Jr. are Miami’s only attractive young players.
  • The Blazers extract every possible asset the Heat have with two first-rounders and a pair of pick swaps in addition to two prospects.
  • Boucher has two years left on his current contract. He’s only owed $11.8 million this year and $10.8 million in 2024-25. He would be a useful player for Portland to keep around as a decent stretch big with defensive versatility who could be part of what’s currently a thin frontcourt rotation.

This deal brings back a decent package of assets that could help Portland move a rebuild forward while helping Lillard get his wish. It’s not ideal for the Blazers, but it’s not the worst possible package either if a third team needs to be involved.

The Brooklyn Nets could be a third team that gets involved in a Damian Lillard-Miami Heat trade.
Brooklyn Nets logo (Photo by Nic Antaya/Getty Images)

Three-team trade No. 2: Lillard to the Heat, Herro to the Brooklyn Nets

This is a respectably fair trade for all three teams.

Again, the Heat get their man in Lillard, but in this deal, Portland also sends Jusuf Nurkic to Miami to get the remainder of the big man’s salary off the books.

The Nets get Herro which, as of July 4, seems to be the most likely landing spot for the Heat guard – so much so that even he appears ready to head to Brooklyn.

And the Blazers, rather than getting the handful of contracts from Toronto, get two massive expiring contracts in Kyle Lowry and Spencer Dinwiddie to go along with all of Miami’s available first-round picks, as well as Jaquez Jr. and Jovic.

This isn’t a trade full of desirable picks and prospects heading to Portland, but the Blazers get the same package of assets from Miami as they do in the Raptors deal, plus they offload a ton of salary. Lowry’s and Dinwiddie’s contracts will clear about $50 million of salary after next season, in addition to the three years and more than $54 million still owed to Nurkic.

If Dame really is going to land in Miami and the Blazers refuse to take Herro in return, this might be the best Portland can do. It adds future picks and two potentially useful prospects to add to the core of Henderson, Simons, and Sharpe, and it rids the franchise of about $100 million in future salary after next season.

It appears the only way Lillard ends up playing for the Heat is if a third team gets involved in a trade. It would be a smarter move for Portland – albeit a cold one – if general manager Joe Cronin ignores Miami’s package entirely and trades Dame elsewhere for a much more enticing return that the Heat simply can’t offer.

But if the decision is to help Dame reach his preferred destination, this Brooklyn trade might be the way to go for the Blazers.

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.