It has been more than two months since seven-time NBA All-Star Damian Lillard told the Portland Trail Blazers he wanted to be traded, and yet, as of today, Lillard remains with the team.
Trade talks have reached a stalemate, with Lillard looking to force his way out and Blazers general manager Joe Cronin looking to get the best package in exchange for Lillard -- whether that's from the Miami Heat or one of the other 28 teams in the NBA.
With no resolution in sight, we asked our NBA experts to play GM for the Heat and three other teams that could potentially pull off a deal for Lillard, making their best possible offer to acquire the franchise guard. We enlisted ESPN front office insider Bobby Marks to decide which proposals make the most sense for Portland.
Lillard takes his talents to South Beach
Miami Heat get: Damian Lillard, Jusuf Nurkic
Portland Trail Blazers get: Tyler Herro, Kyle Lowry, Jaime Jaquez Jr., Nikola Jovic, first-round picks in 2027 and 2029, first-round swap rights in 2028 and 2030.
There is only one Lillard trade that actually makes sense, and that is to the Heat.
Considering both Lillard's age (he turned 33 in July) and his contract (he's owed more than $200 million over the next four seasons), a team taking on Lillard at this point in his career needs to have enough to at least make it interesting for Portland to make a deal yet also enough to remain championship caliber after the trade.
Miami is the only destination where those two lines cross.
A package built around Herro, Jaquez, Jovic, two first-round picks and two more swaps -- both of which are far enough into the future that, if this Portland team grows as it is capable of, could easily bear out as switches -- gives the Trail Blazers current young players to fit alongside their core and future draft capital to add to it in the future.
I like the fit of Herro with Scoot Henderson and Shaedon Sharpe, particularly for a young team. Herro is a really good shooter, can play on and off the ball, and should help create more space for Henderson to operate. For a team very light in the frontcourt, Jaquez and Jovic are intriguing long-term bets. Jovic, in particular, has the upside to fit really nicely alongside Henderson and Sharpe moving forward.
This allows Portland to hand its team over to Henderson fully, without the specter of an unhappy Lillard hanging over the franchise in perpetuity.
It might not be perfect, or one that resembles the Rudy Gobert-to-Minnesota trade in 2022, but that kind of deal simply doesn't exist. This is a good return for Portland that would still leave Miami with a chance to win a title this year and next.
-- Tim Bontemps
GM Bobby says: We have to condition our minds that there is no Gobert, Donovan Mitchell or Kevin Durant trade package coming Portland's way from Miami. This is a good offer and checks the three most important boxes when trading a franchise player: young players, draft capital and financial relief.
Miami could add Caleb Martin and a third unprotected first (if the first owed to Oklahoma City in 2025 is amended) to the package, but the Heat would be bidding against themselves. Portland has to face the realization that there is a nonexistent market right now outside of the Heat.
Would that change if Portland holds on to Lillard into the season and explores moving him closer to the trade deadline? It's possible, but the 33-year-old has played a total of 87 games in the past two seasons, and a future injury would only lessen the return Portland would receive in a trade.
One thing I like about this trade for Portland is Herro not going to a third team. The on-court value of Herro outweighs sending the guard to a third team to acquire an additional first-rounder.
With Herro having four years left on his contract and Anfernee Simons three, the Trail Blazers can pivot with either player in a separate trade in the future.
Resolving the NBA's two outstanding trade sagas
Philadelphia 76ers get: Damian Lillard, Terance Mann, Norman Powell and Robert Covington
Portland Trail Blazers get: Furkan Korkmaz, Tyrese Maxey, Jaden Springer, Nicolas Batum, Amir Coffey, Marcus Morris Sr., 2028 and 2030 first-round picks (from LA Clippers)
LA Clippers get: James Harden and Tobias Harris
If the Sixers entertain dealing Maxey, there's a realistic path to a three-team trade that would fulfill trade requests by Harden as well as Lillard this summer. Lillard is Philadelphia's surest and, more importantly, quickest option for replacing Harden with another star who can help reigning MVP Joel Embiid compete for a title in his prime.
That comes at the cost of sacrificing Maxey, who won't turn 23 until November and averaged 20.3 PPG. Still, this is the peak of Maxey's trade value before he signs the kind of second contract that changed our perception of Herro and Jordan Poole over the past year.
This framework allows the Sixers to rebuild their perimeter depth with 3-and-D contributors Mann and Powell. Meanwhile, the Clippers give up both of their tradable first-round picks to upgrade at point guard and power forward by adding Harden and Harris. They would give the Clippers a strong starting lineup at the cost of depth and future flexibility.
To make this deal, Portland would have to value Maxey more than additional first-round picks, getting only the distant two from the Clippers. Philadelphia doesn't have one to offer until 2029 at earliest and would probably hold the line on including that pick in addition to Maxey.
-- Kevin Pelton
GM Bobby says: The only way Portland engages Philadelphia in trade talks is if Maxey is involved, but Philadelphia has shown no inclination to move its young guard. But let's play the hypothetical game that 76ers president Daryl Morey wakes up one morning and decides to pair Lillard up with Embiid, at the expense of Maxey and the financial flexibility to reshape the roster in the 2024 offseason.
The idea of financial flexibility in 2024 is fool's gold for two reasons. Morey is not known for building a roster with cap space. The lone free agents he has signed with room have been Dwight Howard, Eric Gordon and Ryan Anderson. Also, it's possible the top three free agents available in 2024 are all currently on the 76ers: Maxey, Harden and Harris. This is a reason I would be more inclined to target players under contract for next season (Lillard, Mann and Powell) and not overpay in free agency, even if the cost in a trade is both Maxey and Harden.
For the Clippers, the cost to acquire Harden and Harris is rich (a young player in Mann, expiring contracts and two future first-round picks). But the Clippers are all-in with this roster and could lose Mann to free agency in 2025. The cost is high, but if the goal is to win a championship, this trade gives them the best opportunity, especially when you consider that both Kawhi Leonard and Paul George could leave in free agency next offseason.
On Portland's side of things, the Trail Blazers would have to believe the upside is greater for Maxey than for Herro and the package of young players, first-round picks and swaps they potentially could receive from Miami. Remember also that a Maxey extension (or contract in free agency) could double the $120 million extension Herro signed last October. Those factors would make me pause on moving forward with a 76ers trade.
Bayou backcourt reunion for Lillard
New Orleans Pelicans get: Damian Lillard, Jusuf Nurkic
Portland Trail Blazers get: Zion Williamson, Dyson Daniels, Kira Lewis Jr., Larry Nance Jr. and Naji Marshall
This trade works for what both teams are trying to do. The Pelicans are ready to win right now, while the Trail Blazers need young star power to build toward the future. Done and done.
The Pelicans were battling for first place in the Western Conference when Williamson got injured last season, with All-Star Brandon Ingram averaging a career-high 24.7 PPG. This trade reunites Lillard and Nurkic with CJ McCollum, the core of the 2019 Portland team that reached the conference finals, putting a much stronger team around them. The Pelicans would field a strong mix of players in their prime, youthful athleticism and veteran leadership with depth on both sides of the ball that would give Lillard a very realistic chance to contend during the course of his contract.
The Trail Blazers would get one of the premiere box office talents in the NBA, who is still only 23 years old and is signed for the next five seasons. Williamson would become the team's centerpiece, with Henderson, Simons and Sharpe forming the under-25 nucleus of the future. Williamson is the type of generational talent who is typically never traded, but with his injury history and mercurial offseason storylines, there is a unique window where a fresh start could be good for both sides. Daniels and Lewis are also recent lottery picks still on their rookie deals, and they further fit the Trail Blazers' youth movement.
-- André Snellings
GM Bobby says: Now this is interesting. A seven-player trade that swaps two franchise players and no draft compensation. I like the concept, but let's simplify and clean it up.
Start by removing Nurkic from the deal. I know Portland is looking to rid itself of the three years and $54 million left on his contract. But New Orleans has Jonas Valanciunas under contract for another season, and I would look to extend him rather than take back an unwanted salary. Plus, New Orleans is already in the luxury tax, and this trade adds $7 million in additional salary. By not taking on Nurkic's salary, the Pelicans would need to include the 2027 unprotected first-round pick they're owed from Milwaukee.
Now let's take this one step further and remove Nance. No offense to the veteran, but his $10 million salary puts Portland in a place no rebuilding team wants to be in: the luxury tax. The next step is taking Marshall out of the trade. For this trade to make sense for New Orleans, its depth has to stay intact, which means holding on to the versatile fourth-year forward.
After the multiple back-and-forth calls between the front offices, the trade is now modified to Williamson, Daniels, Lewis and a 2027 unprotected Milwaukee first for Lillard and Keon Johnson (we threw him in to balance the Portland roster).
There is certainly a risk because of Williamson's health history, but this trade delivers Portland something that Miami, Philadelphia and Toronto could not: a franchise player (albeit only when healthy) under contract for the next five seasons. It is important to remember that Williamson's contract is laden with injury, games and weight clauses that protect any team he is under contract with.
New Orleans gets its franchise guard to pair once again with McCollum, retains Ingram and does not deplete its pool of first-round assets.
This trade is not a no-brainer, especially with $200 million left on Lillard's contract (remember, Williamson has the same amount owed also), but it accomplishes two things: It gets New Orleans into the conversation at the top of the West with Denver, Phoenix, Golden State and the Lakers, and it removes the Williamson injury cloud that has hung over the team for the past four seasons.
Lillard as Kawhi 2.0?
Toronto Raptors get: Damian Lillard
Portland Trail Blazers get: O.G. Anunoby, Chris Boucher, Thad Young, Gradey Dick and two first-round picks
Toronto has made a big swing for a superstar before and could be a very intriguing landing spot for Lillard. The Raptors lost Fred VanVleet in free agency and could replace him with Lillard in this scenario.
Anunoby would be the centerpiece of the deal, but it wouldn't be out of line for Portland to push for 2022 NBA Rookie of the Year Scottie Barnes instead.
However, in this version of the deal, the Raptors send Anunoby (who made the NBA's All-Defensive second team last year and led the league in steals) as well as Boucher, Young, Dick (this year's first-round pick), and two future first-rounders. (Any deal with Barnes included could reduce the picks going out).
Lillard gives the Raptors an instant boost on the offensive end and would create one of the league's more potent duos with Pascal Siakam.
As Portland pushes forward with Henderson, Simons and Sharpe, adding someone like Anunoby would instantly give Chauncey Billups someone he can trust immensely on the defensive end.
-- Andrew Lopez
GM Bobby says: There are too many risks for both sides to pull off this deal. I like the concept of swapping out VanVleet for Lillard. But what happens if Siakam does not sign an extension and leaves in free agency? Toronto would be on the hook with the $160 million remaining owed to Lillard and its draft picks depleted (it already owes a 2024 top-six-protected first to San Antonio). There is also the likelihood of Lillard asking out next offseason, considering the roster is less than championship worthy if Siakam leaves. The Raptors could have cap space, and you can make the argument that Lillard, Barnes and Jakob Poeltl are drawing cards for free agents. But when was the last time Toronto signed an All-Star-level free agent? The four-for-one trade would also put Toronto in the luxury tax for only the second time in 20 seasons.
Anunoby is unlikely to sign a $116 million extension, and Portland would have to accept that the cost to retain the forward could top $247 million over five seasons. If the Trail Blazers are comfortable with that figure, then this trade should go on their whiteboard of potential Lillard deals. A foundation of Anunoby, Henderson, Simons and Sharpe is a strong nucleus to build off in the post-Lillard era. The two firsts (likely in 2026 and 2028) have appeal when you consider that Lillard will be three years older and a potential free agent in the 2026 offseason.
If Portland is not comfortable paying Anunoby or there is a threat that it could lose him for nothing in free agency, then the risk is too high to take on the expiring contract for the sake of two future firsts (although possibly in the lottery) and Dick.