The look of resignation on Damian Lillard as he propped himself up after grabbing the back of his ankle was a poignant one. Lillard's nonplussed expression as he waited to be pulled onto his feet was in stark opposition to his signature moment back in 2019, when he expelled the Oklahoma City Thunder at the buzzer in Game 5 and stared right into the soul of the viewing audience.
That aura was gone on Sunday evening. The flood of emotions he must have felt knowing this was the nadir of his career and the gateway to his basketball twilight must have been intense, but he didn't show it.
For every Milwaukee Bucks fan watching or in attendance, this has been a stiff drink season. It carried a foreboding feeling from the beginning: The Bucks started the season winning just one of their first seven games and were always fishtailing between winning streaks and slumps, barely keeping their heads above water against the Eastern Conference elite.
In that way, what happened on Sunday night was a fitting conclusion. Lillard only scored seven points in his second game back from a blood clot issue, but he was damned from the beginning. Too often, Lillard’s career has had a pall hovering over it. The minute he joins an ensemble, a Rube Goldberg device activates a slow-motion disaster.
Achilles injury is yet another chapter in Damian Lillard's star-crossed career
He remained loyal to the Portland Trail Blazers until the very moment they decided to waste his prime on a rebuilding project. His Blazers-era ascendance was halted nearly a decade ago by Wesley Matthews’ Achilles rupture and LaMarcus Aldridge decamping for San Antonio.
The unfortunate truth is that Lillard has always gotten the short end of the team-building stick.
In Milwaukee, he joined a declining powerhouse whose coffers are devoid of lottery picks or high-ceiling neophytes. He’s the Dominique Wilkins of his era, watching Steph Curry soar higher.
Meanwhile, Golden State built multiple iterations of contending lineups around Curry. Their latest one involves Curry chasing a fifth ring alongside the teammate that Lillard sought to play alongside in Miami: Jimmy Butler
Lillard only ended up in Milwaukee because their GM refused to accommodate his desire to play in Miami with Butler. His longtime Blazers head coach, Terry Stott, butted heads with Adrian Griffin on the Bucks staff and left in a huff. Doc Rivers failed to design a scheme that could utilize Lillard off-ball alongside Kevin Porter.
There was a hope that the Bucks could leverage its remaining assets and Khris Middleton, Bobby Portis or Brook Lopez into a legitimate third piece. Butler saw the toxic sludge GM Jon Horst was dumping into the water in Milwaukee and shot them down during his trade saga when the team expressed interest. Unsurprisingly, Kyle Kuzma has been underwhelming as a defender, facilitator and even in his defined role as a tertiary scorer.
Milwaukee winning the NBA Cup in December felt like an aberration that occurred within a vacuum. Technically it did: A win over the Thunder,t the team that broke the NBA record for point differential in a season, was the zenith of the Lillard era for Milwaukee, but it happened in an 83rd game. Nobody cheesed harder than Lillard to finally have a trophy on his case after a decade of watching his arch rival Curry leave him in the dust. However, since then this season has felt like it was teetrering on the brink of disaster.
Lillard suffering this devastating injury against the Indiana Pacers and Tyrese Haliburton is the cherry on top of a curdling season. He wasn’t at full strength at any point in this series and was hobbled for the end of last year's postseason series against Indiana.
Lillard was a suitable No. 2 this season. As usual, though, his chemistry with Giannis Antetokounmpo was solid but lacking the cohesiveness of a championship duo. Their pick-and-roll game never developed and Doc Rivers didn’t force it, so they play their own games worlds apart.
There is no permutation of the future in which Lillard contributes to a contending Bucks team. Lillard has two more years left on his contract after this season; He'll miss all of next season and owns a player option for 2026-27. When he returns in 2027, he'll be 36 and working his way back into game shape for a team that likely won’t include Antetokounmpo.
There is no what could have been with the Bucks. They were always running in quicksand. Now they're fully sunk, the Dame Dolla market is crashing out and the team is trailing 3-1 against the hated Pacers with no way out in sight. As rough as this season was for Lillard, Antetokounmpo and Co., there are darker times ahead.