It was meant to be a statement when the Milwaukee Bucks pulled off the blockbuster trade for Damian Lillard before the 2023-24 season. A message to Giannis Antetokounmpo, a push for another title, and a desperate pivot from a core that had begun to stagnate since their 2021 championship. Instead, it may have sparked a collapse—and cleared the path for a Celtics renaissance.
The deal stunned the NBA. Lillard had spent months lobbying for a move to Miami, a city and franchise he favored. But in the end, Milwaukee swooped in with a win-now move, parting with Jrue Holiday in a three-team trade that seemingly sent shockwaves through the league. What the Bucks didn’t anticipate: it would be Boston who truly cashed in.
With Holiday rerouted to Portland, the Celtics pounced. In a deal struck just before training camp, Boston acquired the veteran guard, trading away Robert Williams, Malcolm Brogdon, and draft picks to bring in a player whose playoff pedigree and defensive tenacity matched their championship aspirations.
The result? A dream season. Holiday didn’t need to be the offensive anchor like he was in Milwaukee—he just had to be himself. Steady. Smart. Clutch. He became the glue for a Celtics squad that had long flirted with greatness but couldn’t quite get over the top. This time, they raised Banner No. 18 to the rafters in TD Garden.
Meanwhile, chaos brewed elsewhere. The Heat—Lillard’s original destination of choice—crumbled under expectations. Their 2023 Finals run became a distant memory after back-to-back first-round exits. The nadir came this year, when they were swept by the Cavaliers in a historically lopsided series. Miami’s drama-riddled season ended with Jimmy Butler traded to Golden State, leaving a hollow shell of a team behind.
Milwaukee didn’t fare much better. Despite Antetokounmpo’s brilliance, the Bucks were dispatched in five games by the surging Indiana Pacers. Worse yet, Lillard’s season—and possibly career—ended abruptly with a torn Achilles in Game 4. At 34, questions swirl around his long-term viability, casting further shadows over Milwaukee’s aging and eroded roster.
The Bucks’ gamble on Lillard was a swing for the fences. But instead of launching another title run, it has left them teetering. With Giannis’ future now uncertain, and only fragments remaining from the 2021 championship team, Milwaukee faces a crucial offseason that could redefine the franchise.
Miami is in a similarly precarious position. Their improbable 2023 Finals run bought some goodwill, but the last two years have erased much of it. The departure of Butler signaled the end of an era, and it’s unclear where the Heat go next. With an aging core, minimal assets, and a talent-drained roster, the climb back to contention looks steep.
In contrast, Boston looks like a franchise finally in command of its destiny. Their title run validated years of development, roster reshaping, and postseason heartbreak. With Jayson Tatum and Jaylen Brown in their primes, and key veterans like Holiday and Derrick White supporting them, the Celtics are built not just for this moment—but for seasons to come.
As the 2025 playoffs roll on, Boston moves forward with confidence, having just dismantled the Orlando Magic in five games. The defending champs remain the class of the East—not just because of their talent, but because of their timing, chemistry, and execution in the wake of others’ missteps.
Ironically, it was the Lillard trade—meant to fortify Milwaukee—that catalyzed Boston’s breakthrough. They capitalized on the fallout, made the right moves, and are now reaping the rewards. Sometimes, the biggest wins come not from the loudest trades—but from the smartest pivots.
The storm clouds hang low over Miami and Milwaukee. But in Boston, the skies are clear—and the path to another banner is wide open.