Milwaukee Bucks Waive Damian Lillard, Stretch Contract to Gain Flexibility But Now Face Serious Depth Issues in the Backcourt
The Milwaukee Bucks are thin on backcourt after waiving Damian Lillard and stretching the remaining $113 million on his contract to land more flexibility. In a move that shocked fans and analysts alike, the Bucks made a cold, calculated decision to move on from the All-NBA guard less than a year after acquiring him. Lillard, once seen as the final piece to push the Bucks over the top, now represents one of the most stunning financial and basketball pivots in recent memory. While the long-term salary cap implications made the move feasible, it’s clear that the decision leaves the team exposed in ways that can’t be measured in dollars alone.
Lillard’s departure leaves the Bucks paper-thin in the backcourt. With Jrue Holiday long gone, and with no legitimate star or even starting-caliber point guard on the roster, the Bucks now find themselves in uncharted waters. The Lillard experiment, though it began with optimism and hype, was derailed by injuries, chemistry issues, and a system that never quite maximized his strengths. Still, waiving him—rather than pursuing a trade or alternative route—has raised eyebrows across the league.
The financial mechanics of the move are fairly straightforward. By waiving Lillard and using the stretch provision, the Bucks will spread his remaining $113 million over the next seven seasons, significantly reducing his cap hit each year. This gives Milwaukee some short-term financial breathing room, which can be used to fill out the roster and potentially take swings on younger players or veterans willing to sign at a discount. But what they gain in cap relief, they lose in immediate star power and offensive creation.
When Lillard arrived in Milwaukee, the pairing with Giannis Antetokounmpo was touted as one of the most explosive duos in the NBA. The hope was that Giannis’ downhill dominance and Lillard’s perimeter shooting would form an unstoppable inside-out combination. For flashes of the season, that vision materialized. But it was never sustained. Injuries to both players disrupted continuity, and defensive liabilities exposed Lillard in high-leverage moments. Add in the midseason coaching change and an early playoff exit, and the Bucks’ championship window looked less like a fortress and more like a fragile pane of glass.
The decision to waive Lillard is, in many ways, an admission by Milwaukee’s front office that the pairing did not—and perhaps could not—work in the way they’d envisioned. But it’s also a risky gamble. There are few—if any—players available who can replicate what Lillard brings offensively. His shooting range alone forces defenses to stretch beyond their comfort zones, opening up lanes for others. Without that gravitational pull, the Bucks’ offense could become far more predictable and easier to defend.
The current backcourt rotation now features names like Malik Beasley, Patrick Beverley, and A.J. Green. While these players have individual strengths—Beasley as a shooter, Beverley as a defender and leader—they aren’t primary ball-handlers or elite creators. Delon Wright was brought in during the offseason, but he’s more of a steady hand than a dynamic threat. None of these options command the kind of defensive attention that Lillard did, and none are suited to shoulder the offensive burden alongside Giannis on a nightly basis.
This puts even more pressure on Antetokounmpo and Khris Middleton to generate offense, a task made more difficult by the aging curve both stars are beginning to confront. Giannis remains a dominant force, but with mounting wear and tear and years of high-usage basketball under his belt, the Bucks can’t afford to overextend him in the regular season. Middleton, meanwhile, has struggled to stay healthy and hasn’t looked like the All-Star he once was in quite some time. Counting on either to fully compensate for Lillard’s absence is a gamble that could lead to stagnation—or worse, regression.
The Bucks’ front office is likely betting that the cap flexibility created by stretching Lillard’s contract will eventually lead to a deeper, more balanced roster. They may be eyeing future free agency classes or trade targets that become available midseason. The idea is that a more versatile, defense-oriented roster could actually be more complementary to Giannis’ skill set than a high-usage scorer like Lillard. But that vision is built on hypotheticals, not certainties.
In the meantime, Milwaukee risks falling behind in an Eastern Conference that’s rapidly improving. The Boston Celtics continue to look like a powerhouse. The Knicks, Sixers, and Cavs are all pushing forward with aggressive moves and ascending cores. Even the Pacers and Magic are trending upward. Milwaukee, once viewed as a perennial contender, now faces the very real possibility of slipping into the middle tier of the conference—too good to tank, but not good enough to win.
The human side of this story also shouldn’t be overlooked. Lillard, a player long admired for his loyalty to the Portland Trail Blazers, took a calculated risk in requesting a trade to Milwaukee. He left a franchise and fanbase that adored him in pursuit of a championship ring. That ring never came, and now he’s left teamless and uncertain about the next chapter of his career. The Bucks, in cutting ties so abruptly, raise questions about how player loyalty is reciprocated—or not—in today’s NBA.
For all the talk of professionalism and business decisions, there’s no doubt this move will affect Milwaukee’s reputation around the league. If stars begin to see the Bucks as a team quick to pull the plug on big investments, it may become harder to attract top-tier talent in the future. Front offices remember how you treat your stars—even when things don’t work out. This kind of move, while fiscally defensible, could create a perception problem.
So where do the Bucks go from here? The answer likely involves some combination of internal development and external acquisitions. Andre Jackson Jr. and MarJon Beauchamp may get more opportunities, though neither is ready to handle major backcourt responsibilities. The free-agent market is thin, but mid-tier veterans like Dennis Smith Jr., Kendrick Nunn, or even Goran Dragić could be short-term stopgaps. The Bucks could also explore sign-and-trade scenarios or look to absorb contracts using the cap flexibility created by stretching Lillard’s deal.
There’s also the looming question of Giannis’ long-term commitment. He has, in the past, been vocal about his desire to compete at the highest level and avoid stagnation. While he re-signed in recent years, he did so with the understanding that the team would remain aggressive in building a title contender around him. Waiving Lillard, rather than finding a way to retool around him, could be seen as a step in the wrong direction. If the Bucks fail to contend again this season, the conversation around Giannis’ future will only grow louder.
From a fan perspective, the move is difficult to digest. The excitement that surrounded Lillard’s arrival was unprecedented. Ticket sales soared, merchandise flew off the shelves, and Milwaukee buzzed with hope. To see it all undone in less than a full season feels jarring and disheartening. Fans understand business, but they also crave continuity and stars they can rally behind. With Lillard gone, the emotional anchor that tied fans to a renewed title push is severed.
Of course, none of this is to say that the Bucks can’t recover. They still have one of the best players on the planet in Giannis, a quality front office with a history of shrewd moves, and a solid supporting cast that, with the right tweaks, could remain competitive. But waiving Damian Lillard is not a footnote—it’s a headline. It reshapes the franchise in profound ways, both financially and philosophically.
Ultimately, the decision to waive Lillard and stretch his remaining salary may be judged not just by what Milwaukee gains in flexibility, but by what it loses in identity, trust, and direction. The Bucks took a swing, missed, and now must find a new way forward—without one of the most dynamic guards of this generation and with a backcourt that’s suddenly running on empty.
It’s a bold move, maybe even a necessary one. But it’s also a risky one. The Bucks have bet on their ability to rebuild around Giannis without the explosive scoring and leadership Damian Lillard was supposed to provide. Whether that bet pays off will define the franchise’s future—and could determine whether this team stays in the championship picture or fades back into the pack.
