Damian Lillard’s future with or away from Portland has been speculated on for almost two years now. He continues to express a desire to remain with the Trail Blazers while the organization has struggled to field a competitive roster around him. Landing the third overall selection in this year’s draft has only fueled more speculation because of the predicament it gives the organization: trade it for players who can help Lillard win now, or draft his potential long-term replacement.
While Lillard has stated that his preference is to remain in Portland, he also says that there would need to be “a separate conversation” on his future if they fail to put a strong team around him. When asked by ESPN’s Brian Custer to rank New York, Miami, Boston, and Brooklyn as potential destinations, he chose Miami as his preference among the group.
Here are the best possible trade offers each of these teams could make in the event Lillard becomes available.
The Heat could make a reasonable offer for Lillard but it may be the weakest among the teams from his rumored group. The most significant piece of their offer would include Tyler Herro, assuming the goal is to unite Lillard with Jimmy Butler and Bam Adebayo.
Portland’s valuation of Herro would be paramount if they were to accept Miami’s trade package over other teams. Other players of value the Heat could include are Caleb Martin, who had a breakout in this year’s playoffs, and recent first-round pick Nikola Jovic. They can also include the 18th overall pick in this year’s draft, as well as their 2028 and 2029 first-round picks.
A potential trade involving Herro would most likely be accomplished once the new league year rolls in when he counts as $27 million for salary matching purposes. They have plenty of matching salaries for Lillard with a combination of their other higher-salaried players like Kyle Lowry, Duncan Robinson, and Victor Oladipo.
The Celtics have two main pathways in a potential trade for Lillard. The first is by moving Jaylen Brown, which would likely only be a consideration for Boston if he doesn’t want to extend with them. Lillard would be an excellent return for Brown in that scenario and could play off Jayson Tatum offensively. Brown will be eligible to sign a supermax extension this summer projected at five years, $285 million.
The other pathway is to trade anything else they can for Lillard to pair him with Tatum and Brown. They could offer a combination of players like Marcus Smart, Robert Williams III, Derrick White, Payton Pritchard, and restricted free agent Grant Williams through a sign-and-trade. They also can trade a maximum of four first-round picks in 2024, 2026, 2028, and 2030. Even if this package appeals to Portland, fielding Tatum, Brown, and Lillard with each making over $50 million in 2025-26 is untenable for Boston under the new CBA.
Brooklyn is another team that is expected to pursue Lillard if he becomes available. He has been seen at Nets playoff home games in April and the team would appeal to him since he’s close with Mikal Bridges. The Nets are well-equipped to make a trade for the next available All-Star after accumulating assets from their respective trades for Kevin Durant and Kyrie Irving.
Although they now have a surplus of future first-round picks, they are motivated to continue competing over the next four years since they owe two of their own first-round picks and two first-round pick swaps to Houston. Their offer would likely be draft picks-based since they can trade a maximum of seven first-round picks this offseason. They can also offer a combination of players like Nicolas Claxton, Dorian Finney–Smith, Cam Thomas, and restricted free agent Cameron Johnson through a sign-and-trade.
The Knicks have the most trade assets among teams that made the playoffs this past season. They had enough to acquire Donovan Mitchell last summer but ultimately chose not to top Cleveland’s offer for him. They can trade up to eight first-round picks this season as well as a combination of players like RJ Barrett, Immanuel Quickley, Quentin Grimes, and Obi Toppin.
While the Knicks will be on the hunt for an All-Star, Lillard doesn’t seem like an ideal target. They don’t need backcourt help anymore with Jalen Brunson playing at an All-Star level. Their biggest needs are at the frontcourt, so it’s possible we see them pursue players like Jaylen Brown, Pascal Siakam, and Joel Embiid, should any of them become available.