PORTLAND, OREGON – APRIL 02: Damian Lillard #0 of the Portland Trail Blazers works against Jrue … [+] Holiday #21 of the Milwaukee Bucks in the first quarter at Moda Center on April 02, 2021 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 Abbie Parr/Getty Images)
Getty ImagesNearly three months after he requested a trade from the Portland Trail Blazers, Damian Lillard finally got his wish Wednesday—to some extent. The Blazers shipped him to the Milwaukee Bucks in a three-team blockbuster that radically reshaped the NBA hierarchy.
In doing so, they revitalized the league’s trade market for the time being.
When Lillard requested a trade on July 1, he made it known that he only had eyes for the Miami Heat. His agent, Aaron Goodwin, „advised other teams not to pursue a trade“ for him because he wanted „to play only for Miami,“ according to Barry Jackson of the Miami Herald.
Lillard’s one-team trade request was relatively unprecedented. He just signed a two-year, $121.8 million extension with the Blazers last summer, which meant he was on a guaranteed contract for at least three more seasons. Lillard’s Miami-or-bust stance sapped the Blazers‘ leverage in trade negotiations, as the Heat had little incentive to offer a fair-value package if they thought they were the only bidders.
In late July, the NBA sent a memo to all 30 teams that said „any future comments, made privately to teams or publicly, suggesting Lillard will not fully perform the services called for under his player contract in the event of a trade will subject Lillard to discipline by the NBA.“ That didn’t cause the rumor mill to stop churning, though. Jackson and Anthony Chiang recently reported that „if Lillard is traded to a team other than Miami, he is expected to ask to be traded to the Heat.“
Despite those reports, it seems as though Lillard is on board with his move to Milwaukee.
That’s great news for a league that was otherwise staring down a major superstar trade problem with no end in sight.
Lillard wasn’t the only player to issue a one-team trade request this summer. After picking up his $35.6 million player option for the 2023-24 season, Philadelphia 76ers guard James Harden made it known that he wanted to be traded to the Los Angeles Clippers.
Unlike Lillard, Harden’s trade request remains unfulfilled for the time being. If he wants that to change, Harden may have to take after Lillard and widen the scope of which teams he’s willing to join.
Trade talks seemingly never got off the ground between Portland and Miami, according to multiple reports, while the Sixers ended trade talks with the Clippers in mid-August, per ESPN’s Adrian Wojnarowski. Once Lillard’s camp realized that they were stuck at a dead end, Goodwin „privately told“ the Bucks and Brooklyn Nets in mid-September that he „would be interested in a deal there,“ per Marc J. Spears of Andscape. Less than two weeks later, the Bucks leapfrogged the Heat to acquire Lillard.
The Lillard trade saga should teach both disgruntled players and their agents a valuable lesson: Teams hate being backed into a corner. One-team trade requests are far less likely to be fulfilled unless that team has a treasure trove of assets that it’s willing to dangle. Otherwise, a player risks being stuck in trade purgatory until his contract expires or he expands his list of destinations.
Had the Blazers caved and taken a suboptimal return from Miami, other stars would inevitably follow suit with their own trade requests. The Bucks did the league at large a favor by not being scared off by Lillard’s Heat-or-bust stance, but they did themselves a favor, too.
This summer, Bucks megastar Giannis Antetokounmpo made it clear that he was suddenly questioning his own long-term future in Milwaukee. Khris Middleton, Jrue Holiday and Brook Lopez were all on the wrong side of 30, and the Bucks‘ title window appeared to be closing within the next few years.
Lillard just turned 33 in July, so age remains a long-term concern for Milwaukee. But Antetokounmpo should no longer have to worry about whether the Bucks are all-in on pursuing championships. He still might not sign an extension until next summer, when he’ll be eligible for a four-year deal worth an estimated $244.9 million, according to Spotrac’s Keith Smith, but he’s likely far less of a free-agent flight risk in 2025 than he seemed to be a few weeks ago.
That’s bad news for Miami and other suitors that were lining up to pursue Antetokounmpo, including the New York Knicks. They’ll now have to turn their attention elsewhere, whether to Harden, Holiday (whom the Blazers received in the Lillard trade and reportedly hope to reroute elsewhere) or another disgruntled star down the line.
That’s great news for the NBA trade market at large, though.
Had the Bucks stood pat and not gone on a deep playoff run in 2023-24, speculation about Antetokounmpo’s future would have reached a fever pitch. Teams interested in trying to acquire him might have been more risk-averse with other trades in the meantime, as they’d need to preserve as many assets as possible. That could have ground the star trade market to a halt for the next two years.
With Antetokoummpo now likely off the market for the time being, teams can pivot right away. Sixers center Joel Embiid and Dallas Mavericks guard Luka Doncic are the two names worth monitoring in that regard, although neither player has indicated that a trade request is imminent.
If Embiid, Doncic or another megastar does eventually request a trade, this Lillard deal could also help reset the market after the Minnesota Timberwolves‘ ill-advised acquisition of Rudy Gobert last summer. That deal set an unrealistic baseline for any star trade, as the Wolves gave up four first-round picks, a first-round pick swap, Walker Kessler, Malik Beasley, Jarred Vanderbilt, Patrick Beverley and Leandro Bolmaro for him.
The Gobert trade happened under the NBA’s previous collective bargaining agreement, but some of the changes in the new CBA increased the value of draft picks. The Bucks had already traded away their 2025 and 2027 first-round picks and swap rights in 2024 and 2026 (for Holiday, ironically), so all they could offer Portland was their unprotected 2029 first-rounder and swap rights in 2028 and 2030.
Under the old CBA, that might not have been enough draft compensation to get the Blazers to agree. But since they’re looking to flip Holiday (presumably for more picks and/or young prospects) and acquired 2018 No. 1 overall pick Deandre Ayton in the Lillard deal, they didn’t need an outrageous number of picks to part ways with Lillard.
Rebuilding teams like the Oklahoma City Thunder, Utah Jazz and San Antonio Spurs can assemble pick-heavy packages that blow other suitors out of the water. But thanks to the Lillard deal, contenders now have hope that they can still join the bidding for stars even if they aren’t overflowing with future picks.
Rival teams are likely despondent about the Lillard-Antetkounmpo pairing in Millwaukee and what it means for their short-term title hopes. But the Bucks have restored some much-needed equilibrium to the NBA trade market, which should behoove the whole league moving forward.
Unless otherwise noted, all stats via NBA.com, PBPStats, Cleaning the Glass or Basketball Reference. All salary information via Spotrac or RealGM. All odds via FanDuel Sportsbook.