About four years ago in this space, I wrote about how the Milwaukee Bucks had made the leap to becoming legitimate contenders to make the NBA Finals. They came up just two games short of getting there in that 2018-19 season, but it was clear the title window had opened for the franchise that had been mired in decades of mediocrity.

Much of that had to do with Giannis Antetokounmpo emerging as a generational star, winning the first of two MVP awards that season, but that was a year we also saw Mike Budenholzer take the reins as head coach, Khris Middleton make his first All-Star team, and a championship roster begin to take shape—headlined by the key offseason signing of Brook Lopez.

Two seasons, a global pandemic, a Jrue Holiday trade, and a playoff run for the ages later, the Bucks would bring the Larry O’Brien trophy to Milwaukee and we’d have a championship parade in the city for the first time since the 1950s. That was pretty great!

Now, the Bucks are chasing a different kind of history. Winning one title, especially with the way it happened in 2021, cements a team’s place in NBA history forever. But winning multiple titles is something different. The NBA is a league of dynasties, and the teams that get remembered as all-time greats are ones that bring home the hardware. This season is perhaps their best chance to join those ranks and become the team of the 2020s.

Last season, the Bucks season ended after a hard-fought, seven-game series, losing to the Boston Celtics. But the Bucks were missing Middleton for all seven games, and repeating as champions in the NBA is incredibly difficult. Repeating after the shortest offseason in NBA history because of the pandemic-altered schedule—and in an offseason where Middleton and Holiday would join Team USA to win a Gold Medal in Japan—would have been a tall task for any great team, even one at full health.

The team that perhaps offers the best historical comparison to these Milwaukee Bucks are the Tim Duncan-era San Antonio Spurs, another great team that never won back-to-back. The Spurs won five titles between 1999 and 2014—including three in five seasons between 2003 and 2007—but they never repeated as champions.

The Bucks are structured similarly to many of those Spurs teams. They have Giannis Antetokounmpo as the perennial MVP candidate, and one of perhaps the 10 best players of all time (hold that thought!) in the Duncan role as the team’s one true superstar. Antetokounmpo is flanked by two exceptionally talented perimeter players in Khris Middleton and Jrue Holiday, not unlike Duncan with Tony Parker and Manu Ginobili. Middleton and Holiday, like Parker and Ginobili, are borderline All-Stars in the regular season who have shown the ability to go up a level in the postseason and deliver when it counts. Comparisons could be made between Bucks’ veterans like Lopez, Pat Connaughton, Bobby Portis, and Wes Matthews and the likes of Bruce Bowen, Brent Barry, Robert Horry, and Michael Finley for the Spurs in the mid-’00s. Budenholzer being an assistant coach under Gregg Popovich for nearly 20 years—including the first four of the Spurs’ championships—is an obvious thread connecting the teams from Milwaukee and San Antonio.

Of course, the small market factor is there, too. San Antonio and Milwaukee rank among the five smallest media markets in the NBA, and there always seems to be a team from Los Angeles or New York grabbing more attention than the low-drama small market success stories like the Bucks and Spurs.

What it boils down to is basically this: The Bucks are the Spurs, but cool.

Like those Duncan-era teams, the Bucks are going to be in the mix, competing for titles year after year. They won’t always be the favorite, but as long as Giannis and their core pieces are intact, the Bucks will be contenders.

Under Duncan, especially in the earlier years, the Spurs often flew under the radar as a plodding, boring team that won through defense and bank shots. They weren’t cool, and only real basketball dorks (like, well, me) rooted for them over the Shaqs and Kobes and LeBrons of the world.

The Bucks, while also flying under the radar from time to time, are not boring. No team with Giannis Antetokounmpo leading the charge ever could be. The amount of WOW! plays he delivers on a night-to-night basis is just incomprehensible. He’s so consistently brilliant on both ends of the court that it lifts the rest of the team. That’s what you want out of a superstar. What more can you even say about Giannis? He’s the best. We’re so lucky he’s in Milwaukee.

Antetokounmpo, who turns 28 on December 6, is already climbing the ranks of the all-time greats. With two MVPs, a Defensive Player of the Year award, and a Finals MVP—punctuated by one of the greatest performances in NBA history dropping 50 points in the closing game—he’s already a surefire Hall of Famer and one of the defining players of his generation. In the heart of his prime, he might even still be getting better. He could very well win his third MVP this season.

Last year, as part of the NBA’s celebration of its 75th season, Antetokounmpo was honored as one of the 75 best players in league history in a ceremony at halftime of the 2022 All-Star Game. Many in the NBA media world ranked those top 75 all-time players, and while it’s difficult to determine where active players might land in those all-time ranks, Giannis is poised to join rarefied air among the best to ever do it.

Let’s talk for a moment about where exactly he already ranks among the best of all time. Because I know we recognize Antetokounmpo’s greatness around here, but getting a sense of where he fits among the greatest of all-time might offer some perspective on the man we get to watch game after game here in Milwaukee.

In those top 75 rankings, ESPN put Giannis at 18th all-time and The Athletic had him at 24th. Those placements mostly centered on where he ranked among other players at his position of power forward. It’s fair to suggest that he is in a tier with Hall of Famers Charles Barkley, Karl Malone, Kevin Garnett and Dirk Nowitzki. Considering Giannis’ age, he’ll likely move past that group in the years to come. Other big men in the top 25 on both of those lists include Moses Malone and David Robinson, and Giannis could move past them, too (ESPN already has him ahead of Robinson). Legendary forwards Julius “Dr. J” Erving and Elgin Baylor and guard Jerry West also rank in the top 20 in both lists (and ESPN already has Giannis ahead of Baylor and West). Passing that group would put Giannis into the top 15 all-time.

Among all-time big men, Giannis still has a ways to go to catch this trio of MVP and multiple-time Finals winners: Hakeem Olajuwon, Shaquille O’Neal, and Tim Duncan. That will essentially be the group Giannis is chasing. To join them, he’ll need to win another championship. And Giannis and the Bucks have a real chance to win another championship this season.

They started the season 9-0, their best start in team history, and have the second best record in the league despite Middleton not yet having seen the court and other key players missing time with injury. And this is not a season where there is a runaway favorite. Along with the Bucks, the Boston Celtics look to be every bit the contender they projected to be, but other Eastern Conference teams like Philadelphia, Brooklyn, and Miami have underwhelmed to start the season. In the West, which is always a gauntlet, Phoenix and Denver are at the top of the standings, and Golden State will always loom as a postseason threat as long as Stephen Curry is there, but there is no singularly dominant frontrunner like we’ve seen in some other years, and even the best teams have some real flaws.

The Giannis-era Bucks are already stamped as all-time greats with the 2021 title. But winning another championship this year could move them from the likes of the 2004 Pistons, 2008 Celtics, 2011 Mavericks or 2019 Raptors toward something greater. The Kobe-Pau Gasol Lakers won titles in 2009 and 2010, the LeBron-Wade Heat teams won twice in the early 2010s, and Hakeem’s Rockets won twice in the ‘90s. Winning twice in three seasons would vault these Bucks up a level among the great teams in NBA history and put Giannis on a path to becoming one of the top 10 players of all-time. And really, there’s no ceiling when it comes to what Giannis Antetokounmpo might achieve.

There is some added urgency to winning in 2023 because the Bucks’ chances of winning a title could change after this season, too. Brook Lopez, a crucial core piece of this team, is in the final year of a four-year contract. Following back surgery that kept him out for most of last season, he has somewhat improbably returned better than ever. During the offseason, he revived his three-point shot that earned him the “Splash Mountain” nickname—detailed brilliantly here in this piece by The Athletic’s Eric Nehm—and is a legitimate defensive force, leading the league in blocks per game and getting deserved Defensive Player of the Year buzz. As good as he’s been, though, he’s still 34 years old and is a year removed from a serious back injury, so there’s no telling how many more years this level of play can be maintained.

In the NBA, it’s hard to keep a great team together and it’s tough to build sustained success. The Bucks are indeed doing that now. But that doesn’t mean the clock isn’t ticking. While Giannis is firmly in his prime, Holiday and Middleton are also in their 30s, and the rest of the Bucks’ roster is more of a veteran squad than one loaded with young prospects. This is a team built to compete now.

They can compete now. With Middleton on the verge of returning (any game now, maybe?), offseason addition Joe Ingles getting closer to recovering from an ACL injury, and the inevitable trade deadline deal that General Manager Jon Horst makes every season, there’s every reason to believe this team will continue to improve on its way to the postseason.

The Bucks, like the Spurs before them, are the small market team with the superstar who stayed, and are built to compete every year. That’s exactly the situation we’d all hoped for when fans rallied to save the team from relocation when the franchise’s future was in question, pre-Fiserv Forum. But now, in the fifth season of the title window being open, the Bucks have more of a pressing need to win now, and a win now would have serious historical significance for the Bucks and for Giannis.

They could truly become one of the iconic teams of this generation.

Which still, is a bewildering thing to say about the Milwaukee Bucks, of all teams, considering the 30-plus years that preceded this incredible run of success. But this is where we are. Led by one of the most exceptional talents the NBA has ever seen, the Bucks are chasing history now. And we are truly lucky to be in Milwaukee and to be along for this ride.


About The Author

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Dan Shafer is a journalist from Milwaukee who writes and publishes the weekly column and online publication, The Recombobulation Area. He previously worked at Seattle Magazine, the Milwaukee Business Journal, Milwaukee Magazine, and BizTimes Milwaukee. He’s won 13 Milwaukee Press Club Excellence in Journalism Awards. He’s on Twitter at @DanRShafer, where he's probably tweeting about the Bucks.