Milwaukee Bucks Fans Feel Betrayed Watching Damian Lillard and Jrue Holiday Thrive Together as Former Stars Turn Into Fierce Rivals
There are painful moments in sports that stay with fans forever—the game-losing shot, the injury at the worst possible time, the trade that breaks up a championship team. But for Milwaukee Bucks fans, there may be no deeper cut than watching two of their recent point guards, Damian Lillard and Jrue Holiday, now suit up for rival teams and work indirectly—but undeniably—against the franchise they once helped lead. If it feels like your exes have teamed up to make your life miserable, that’s not far from what many Bucks fans are feeling right now.
In the span of just over a year, the Bucks’ point guard position went from one of their greatest strengths to one of their most emotionally charged topics. Jrue Holiday, beloved in Milwaukee for his unselfish play, elite defense, and heroic performances during the 2021 title run, was traded to Portland as part of the blockbuster deal that brought in Damian Lillard. That trade shocked fans—not because Lillard wasn’t a star in his own right, but because Holiday was so deeply embedded in the team’s identity. Losing him felt like more than a basketball decision; it felt like losing a part of the soul of the squad.
Then came the twist that made everything worse: Holiday didn’t stay in Portland. He was rerouted almost immediately to the Boston Celtics, the very team the Bucks have battled with for Eastern Conference supremacy. Holiday, the quiet assassin, quickly became the final piece of Boston’s championship puzzle, helping the Celtics win the 2024 NBA title—exactly what Milwaukee hoped to do when they traded for Lillard.
Now, as the 2025–26 season approaches, Bucks fans are living in a surreal NBA universe where two of their most iconic backcourt stars are not only gone but potentially standing in the way of the franchise’s title hopes. Damian Lillard remains in Milwaukee, still elite and still chasing a ring, while Holiday is thriving as the Celtics’ emotional anchor and defensive heartbeat. It’s the basketball equivalent of watching your two exes start a power couple podcast that takes shots at you every week.
The pain is made worse by the emotional investment fans had in both players. Holiday wasn’t just a good fit on the court; he was an exemplary figure off it. Known for his philanthropy, humility, and calm under pressure, Jrue was the kind of player fans dream of rooting for. His steal-and-lob to Giannis in Game 5 of the 2021 Finals is etched into Bucks lore as one of the franchise’s defining moments. His departure was business—but it felt personal.
Lillard, on the other hand, arrived with huge expectations. After years of loyalty in Portland and countless clutch shots, Dame was seen as the final piece to help Giannis return to the top. But Lillard’s first season in Milwaukee was rocky. Injuries, coaching changes, and a lack of chemistry disrupted what should have been a seamless fit. Instead of the smooth offensive juggernaut fans envisioned, the Bucks sputtered in the postseason and were eliminated early—while Holiday was busy helping the Celtics dominate on both ends of the floor.
That’s when the comparisons really started to sting.
While Lillard remains one of the league’s most dangerous offensive threats, his defensive limitations have been exposed in playoff settings. Holiday, conversely, continues to be one of the best perimeter defenders in the NBA—an absolute menace to opposing stars and the kind of player who wins games by doing the little things that don’t show up on highlight reels. Watching him lock up Miami’s backcourt or disrupt New York’s ball movement last postseason reminded Bucks fans of everything they lost—and everything they once had.
And now, as Boston gears up for another title run with Holiday firmly entrenched as their defensive leader and clutch playmaker, it’s hard not to feel like the Bucks accidentally handed their fiercest rival the final ingredient to a dynasty. It’s the kind of twist that would make soap opera writers jealous.
It doesn’t help that Holiday and Lillard have shown great mutual respect—and in some moments, eerily complementary skill sets. Holiday doesn’t need the ball to make an impact, while Lillard thrives when given space and shooters around him. Had they ever been on the same roster, they might have been a devastating backcourt. But instead, they’ve been cast in opposite roles in an ongoing drama that seems written to torment Milwaukee fans.
There’s also a sense of what might have been. If Milwaukee had found a way to acquire Lillard without giving up Holiday, could they have created the best guard tandem in the NBA? Could the Bucks have built a team with Lillard’s scoring and Holiday’s defense coexisting alongside Giannis? Instead, in their pursuit of offensive firepower, they sacrificed their best defender—and now that very defender is neutralizing their path to a championship.
This isn’t to say the Lillard trade was a mistake. Few would argue that. When a player of Lillard’s caliber becomes available, you go get him—especially when Giannis is demanding more help to stay committed. But there’s no denying the emotional toll that came with the cost. Watching Holiday succeed elsewhere, and especially in Boston of all places, is like watching your childhood best friend marry your biggest rival. It’s the perfect storm of heartbreak and helplessness.
The upcoming season will only amplify these feelings. The Bucks are in a make-or-break year. Giannis has signed long-term, but with conditions: they must keep winning. Lillard is still elite, but he’s aging. Middleton and Lopez are battling time. The roster has depth concerns. And Boston, thanks in part to Holiday, looks like the team to beat once again.
Bucks fans are trapped in a basketball version of déjà vu—watching their former hero, now clad in green and white, continue to do all the little things that once made Milwaukee great. It’s a reminder that while stars win games, role players—especially elite ones like Jrue—win championships.
There’s a cruel irony in how the story has played out. Lillard and Holiday weren’t enemies. They weren’t traded for each other in a traditional one-for-one swap. And yet, they’ve become emblematic of different paths the Bucks could have taken. One is the path of continuity and defensive identity, the other of bold offensive reinvention. And right now, the path not taken is the one holding the Larry O’Brien Trophy.
For fans, this isn’t just about strategy. It’s about connection. Holiday was family. Lillard is a welcomed guest. There’s a difference. You celebrate both, but only one grew up with you, struggled with you, and made you believe when nobody else did. Losing that—watching it thrive elsewhere—hurts.
Still, this is sports. There’s always another chapter. The Bucks still have Giannis. They still have a shot. And if Lillard can return to form, if the supporting cast can step up, and if chemistry finally clicks under Doc Rivers, Milwaukee can still compete. They can still win it all. And if they do, the story will shift again—this time with redemption at the center.
But until then, every time Jrue Holiday dives for a loose ball, nails a clutch three, or shuts down an opposing star, Bucks fans will feel a sting of nostalgia and what-ifs. And every time Lillard takes the floor, they’ll hope that their current star can silence the ghosts of the past—and prove that Milwaukee made the right choice in a gamble that, so far, has only deepened their emotional investment in a drama that just won’t end.
In the NBA, like in life, breakups are hard. Watching your exes thrive together? That’s a whole different level of pain.
