With Damian Lillard's time in Milwaukee coming to an abrupt end, what's next for the star guard?

Yahoo

20 hours ago

The Milwaukee Bucks are waiving superstar point guard Damian Lillard, using the stretch provision in the NBA's collective bargaining agreement to wipe the final two years and $113 million of his contract off of their balance sheet, ESPN's Shams Charania reported Tuesday.
The dramatic move comes just over two months after Lillard, who turns 35 in two weeks, ruptured his left Achilles tendon during Game 4 of Milwaukee's first-round playoff matchup with the Indiana Pacers — an injury that's expected to keep him sidelined for most, if not all, of the 2025-26 NBA season.
Advertisement
It will also create the salary-cap space for the Bucks to sign free-agent center Myles Turner, who helped lead the Pacers to the 2025 NBA Finals, to a four-year, $107 million contract to man the 5 spot next to Giannis Antetokounmpo — giving Milwaukee's two-time MVP a new floor-spacing, rim-protecting frontcourt running buddy after the similarly styled Brook Lopez, Antetokounmpo's partner for the last seven seasons, agreed to terms to join the Los Angeles Clippers on Monday, after the start of the NBA's 2025 free agency period.
The waive-and-stretch brings an abrupt end to Lillard's 21-month tenure in Milwaukee — a time that seemed poised to produce one of the great inside-out partnerships in recent NBA history, but that wound up, due to a combination of ill-timed injuries, inconsistency and awful luck, leading to zero 50-win campaigns, zero postseason series victories, and just three total playoff game wins over two seasons.
Viewed through one lens, it's a brutal twist of the knife for Lillard, who finally pushed his way out of Portland after 11 seasons as the Trail Blazers' standard-bearer in pursuit of greener championship-contending pastures, but whose best-laid plans never came to fruition.
Advertisement
Lillard produced, because he always does: 24.6 points on .604 true shooting, 7.0 assists and 4.5 rebounds in 35.7 minutes per game across two seasons in Milwaukee, finishing 10th in the NBA in points and assists per game and 11th in offensive estimated plus-minus last season. But he never quite found a rhythm in the two-man game with Antetokounmpo, never quite established the short-hand that can help make a team more than the sum of its all-time great parts, and never quite proved to be the order-of-magnitude offensive upgrade that justified moving on from defensive title-winning stalwart Jrue Holiday — a realization that proved particularly painful when Holiday got re-routed to Boston and immediately became a vital two-way contributor to the Celtics' 2024 NBA championship.
The ending feels particularly devastating for Dame considering all that precipitated it. He'd been diagnosed with a blood clot in his right calf in late March, mere weeks before the end of the regular season, an affliction that many expected would sideline him for the remainder of the Bucks' season. But he fought his way back in time for the second game of Round 1 against Indiana, a quicker recovery than 'has [ever] been seen before' … only to tear his Achilles just six minutes into Game 4.
While plenty of observers saw the injury as an inflection point for Lillard — a moment that could come to define the final act of the career of one of the 75 greatest players in NBA history — I'm not sure anyone expected it to be followed, barely two months later, by the Bucks cutting bait on him. Everyone knows the NBA is a business; every once in a while, though, you're reminded just how cold it can be.
If you view it through that lens, that is:
While we wait to see where Lillard lands, the Bucks move on.
Advertisement
The stretch provision allows NBA teams to waive a player by taking the amount of guaranteed salary he's owed and spreading it out over a period of twice the number of years remaining on his contract, plus one more season — provided the stretched amount does not exceed 15% of the salary cap. (This, as Fred Katz recently explained at The Athletic, is why the Suns can't stretch what's left of Bradley Beal's deal; in combination with the previously stretched contracts of E.J. Liddell and Nassir Little, going that route would leave Phoenix with an amount of dead money larger than 15% of this season's cap line.)
Lillard was just about to start the two-year, $112.6 million extension he signed with the Portland Trail Blazers back in the summer of 2022. Stretching that amount creates a dead-money charge just north of $22.5 million — about $680,000 south of 15% of the cap, according to ESPN's Bobby Marks — and the Bucks will have to carry that historically large number on their books in every season through 2030.
That unmovable $22.5 million annual charge looms as a mammoth roster-management impediment for Milwaukee over the next half-decade — the kind of prolonged and protracted dead weight that can make maneuvering in pursuit of title contention through the back end of Antetokounmpo's prime even more difficult than it already figured to be. But with Giannis only guaranteed to be under contract in Milwaukee for two more seasons — he holds a $62.8 million player option for 2027-28 — the only future the Bucks can realistically plan for is the one right in front of their faces.
Advertisement
And so: yet another incredibly aggressive win-now move from the team that brought you the trades for Holiday and Lillard (not to mention like a decade's worth of second-round picks for Nikola Mirotić and Jae Crowder).
General manager Jon Horst and the rest of the Bucks' braintrust decided that attempting to avoid wasting the first of those two guaranteed Giannis seasons on a gap year while Lillard, now essentially a $54.1 million dead cap hit for next season anyway, rehabilitates — that moving on from him in a fashion that allowed them to replace Lopez with a younger championship-caliber 3-and-D center in Turner, and hopefully putting themselves in position to remain in the playoff picture in an Eastern Conference ravaged by injuries and roiling in uncertainty — was worth swallowing hard and taking that $22.5 million year-over-year hit.
After all, Antetokounmpo is 30 years old, still performing at an MVP level, and very clearly focused on continuing to pursue a second NBA championship. He is the face of the franchise, the prime mover in all things Bucks, the greatest player Milwaukee has seen since Kareem Abdul-Jabbar, the one who brought the organization back to the mountaintop after 50 years away; if you're not doing everything you can to make him happy, to make sure he wants to stay, to give him a team that he believes he can lead back to that summit, then what are you really doing?
Advertisement
Whether Tuesday's breathtaking revision of the Bucks' financial and on-court future accomplishes those goals — making him happy, making sure he wants to stay, giving him a team he can believe in — remains to be seen. Some reporting suggests that Antetokounmpo didn't like the Bucks moving on from Lillard in this manner; some suggests that Antetokounmpo and Turner 'valued the opportunity to partner together on the court,' and that Giannis effectively recruited Turner to Milwaukee. Your mileage, as ever, may vary.
The Bucks exited the regular season looking to be all but out of options to construct a contending roster around Antetokounmpo over the balance of Lillard's deal. They exit the first two days of free agency having added Turner in Lopez's place, brought back Bobby Portis, Gary Trent Jr., Kevin Porter Jr., Taurean Prince and Jericho Sims, flipped Pat Connaughton's contract (with a pair of future second-rounders) for Serbian guard Vasilije Micić (who's reportedly heading back to Europe, the savings from which should finish the job of creating the room to add Turner), and landed Gary Harris as another backcourt shooter off the bench to join holdovers Kyle Kuzma and 2024 second-round pick Tyler Smith, with A.J. Green, Andre Jackson Jr. and Chris Livingston all on non-guaranteed deals, and Ryan Rollins lingering in restricted free agency.
It feels like you have to squint awfully hard to see that core contending for an NBA championship. In a decimated East, though — with the Celtics shedding starters for luxury tax relief, with the Pacers now down the starting point guard and starting center from their Finals team, with the Knicks still lacking a head coach — you might be able to convince yourself that, with Antetokounmpo leading the charge, this revamped version of the Bucks has as good a puncher's chance as some of the other reloaded outfits (Orlando, Atlanta) that are now taking aim at the top of the conference. And if that's the way Giannis feels — if he sees this as a step in the right direction, despite the discomfort of bidding Dame adieu — then it's the path the Bucks had to walk.