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Bang for the Bucks: Landing Lillard is another remarkable moment for Milwaukee
The move brings about another thrilling phase of the most successful era in the history of Bucks basketball
The Recombobulation Area is a ten-time Milwaukee Press Club award-winning weekly opinion column and online publication written, edited and published by longtime Milwaukee journalist Dan Shafer. Learn more about it here.
Look, I know this is typically a political opinion column, but if something momentous happens with my beloved Milwaukee Bucks, you’re getting a few words from me about it here at The Recombobulation Area. Trading for Damian Lillard qualifies as something truly momentous — discombobulating as it might be — so here we are. Longtime subscribers shouldn’t be surprised.
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With this deal for Damian Lillard, Milwaukee has again bucked the system, coming from seemingly out of nowhere to make the trade of the year.
This deal is a stop-you-in-your-tracks sports moment. It’s an absolutely shocking turn of events. The Bucks are acquiring one of the best players of his generation. This is genuinely, stunningly, preposterously remarkable, and perhaps the biggest trade in Wisconsin professional sports history.
The fact that this came as such a surprise only adds to the head-spinning euphoria of this deal. In reports leading up to the trade, the Bucks were really only mentioned as an afterthought in negotiations. The Miami Heat has been the team tied most closely to a Lillard trade for months on end, and the Toronto Raptors arrived as the late front-runner in a Sept. 25 report from from Marc Spears at ESPN – a report that named the Bucks as a team that has “shown interest since Lillard’s initial trade request,” grouped along with the Philadelphia 76ers, Boston Celtics and Chicago Bulls. But it was the Bucks who made it happen in the end. Much like when they acquired Jrue Holiday in 2020, the Bucks are again the small market franchise upsetting the NBA’s big market apple cart. The team from Milwaukee – mired in years of mediocrity and which faced very real relocation threats just a decade ago – is now proving to be one of the defining teams of this era. Trading for Damian Lillard is a gargantuan move for the Milwaukee Bucks and will keep them in championship contention for the foreseeable future.
The Bucks are sending out Jrue Holiday as the centerpiece of this deal, and yes, I am the guy who wrote in 2019 that the Bucks should trade for Jrue Holiday (and wrote as much again here at The Recombobulation Area weeks before the trade happened), so I have a lot of complex emotions about this, as you might imagine. I have immensely admired Holiday’s work both on and off the court during his time in Milwaukee, so losing him stings, to be sure. He will always be one of my favorite players. Jrue Holiday helped bring a championship to Milwaukee for the first time in 50 years, was responsible for the single greatest play in the history of organized sports, and he elevated the Bucks from contenders to champions. His jersey absolutely deserves to be retired in the rafters at Fiserv Forum when the time comes. He will forever be a Milwaukee legend.
But when you have the opportunity to acquire someone like Damian Lillard, you have to do it. And considering so many factors, from contracts to assets to talent to draft picks and so on, trading Holiday was the only way to make this deal happen. Holiday is an incredible two-way player and a borderline All-Star every season, but Lillard is simply on another level, particularly as a scorer, and that’s where the Bucks have fallen short in the playoffs. The Bucks — and Holiday — have struggled offensively in the postseason, and Lillard is one of the very best scorers in the league and his track record as a clutch performer in big moments is unassailable. This is a spectacular move, and a no-brainer for the Bucks.
The NBA moves fast. The Bucks have been championship contenders since the 2018-19 season, but in order to keep that title window open, evolution is essential. Not many teams can extend that title window beyond a few years. As the two-time MVP and one of the 20 greatest players of all time, Giannis Antetokounmpo is perhaps the best centerpiece to build a team around of this era, but with how talented and competitive the NBA is now, even his presence is no guarantee the Bucks are championship contenders without the right pieces around him.
The Jrue trade in 2020 flipped the script as the team’s first truly all-in moment, following two straight postseasons that began with championship potential but ended in disappointment. It worked, of course, bringing a title to Milwaukee for the first time in 50 years. But in order to compete for another one, you have to keep evolving.
It might not seem like it, but those three seasons in which Holiday was a Buck is a long time in the NBA. One title-winning season followed by two injury-hampered postseasons where the team came up short — with an especially crushing defeat in the first round in year three — means it's time for a new evolution. You can't win in the NBA these days unless you're constantly moving forward.
Moving on from coach Mike Budenholzer after five seasons and hiring a new coach in Adrian Griffin this offseason was part of that, but running back essentially the same roster would have been emblematic of an uncomfortable stasis. With Giannis Antetokounmpo dialing up the pressure on the organization this offseason to remain as committed to winning as he is, a certain level of change to the makeup of the roster seemed inevitable.
But certainly not to this degree. This trade exceeds any expectations for what the Bucks might have done to shake things up. When you have someone like Giannis, an all-world talent who could become an unrestricted free agent after the 2024-25 season, you need to do everything possible to maximize that title window and go all-in to win. Unlike other franchises that have faltered at that goal in the past, the Bucks are going above and beyond.
Superstars like Damian Lillard do not become available often. Even as it seemed unlikely that the Bucks could make an offer to trump others, it stood to reason that Jon Horst — always relentlessly aggressive as the team’s general manager — would get the Bucks into the mix to see what’s possible.
Antetokounmpo and Lillard have been part of the mutual appreciation society together for some time — always speaking fondly of each other’s game, their loyalties to their respective cities, and their ultra-competitive approach — and there are a few breadcrumbs leading to the two megastars joining forces in Milwaukee.
And while Lillard might not be on the same MVP level as Giannis, he is indeed a megastar. The Bucks have never before acquired someone with this kind of star power. The team is now even hosting a welcome rally at Fiserv Forum on Saturday, Sept. 30. That just doesn’t happen for any standard trade. Landing Lillard is different.
In his 11 seasons in Portland, Damian Lillard was a seven-time All-Star, seven-time All-NBA selection, and was named to the NBA’s 75th Anniversary team, honoring the best 75 players in league history. He placed in the top eight of MVP voting in five different seasons. On two separate occasions, he hit a game-winning shot to clinch a playoff series.
Lillard’s offensive skill set, as a perimeter scorer and creator who has unlimited range from beyond the arc, complements Antetokounmpo about as well as anyone not named Stephen Curry. The possibilities for what Giannis and Lillard could accomplish together offensively are out of this world (The Athletic’s Eric Nehm gets into that in more detail here).
The team’s defense will be different, of course, where Lillard is not close to being the same caliber as Holiday, perhaps the league’s best at the point-of-attack defender. But with two perennial Defensive Player of the Year candidates in Giannis and Brook Lopez anchoring the back end, the Bucks should still be a very good defensive team.
They’ll also still have All-Star forward Khris Middleton on the wing, who looks to have much more space to operate with the attention Giannis will draw in the paint and Lillard beyond the arc. The Bucks also parted ways with Grayson Allen in this deal, but keep key role players in Bobby Portis and Pat Connaughton, as well as offseason addition Malik Beasley and promising second-year player MarJon Beauchamp.
All of the pieces are there for the Bucks to contend for another championship. And with a player like Giannis Antetokounmpo in his prime at 28 years old, the Bucks need to be competing for a championship every year. Now, with Damian Lillard – who will be under contract through at least the 2025-26 season – the Bucks’ title window has been extended, and the likelihood that Giannis stays with the Bucks only rises.
The five years under Budenholzer, with three years with Holiday, brought about the greatest era in the history of Milwaukee Bucks basketball, and the team’s first championship since 1971. Now, with the addition of Damian Lillard, this remarkable era enters another thrilling phase.
It’s Dame Time in Milwaukee. Can you believe it, Bucks fans?
To quote Giannis Antetokounmpo, in his text to Lillard after the deal was announced, “Let’s get this f--king championship.”
Dan Shafer is a journalist from Milwaukee who writes and publishes The Recombobulation Area. He’s also written for The New York Times, The Daily Beast, Heartland Signal, Belt Magazine, WisPolitics, and Milwaukee Record. He previously worked at Seattle Magazine, Seattle Business Magazine, the Milwaukee Business Journal, Milwaukee Magazine, and BizTimes Milwaukee. He’s won 17 Milwaukee Press Club Excellence in Journalism Awards. He’s on Twitter at @DanRShafer.
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