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New Territory: Unpacking Milwaukee’s Gamble on Damian Lillard

The Bucks shocked the NBA world with another blockbuster of a trade.

NBA: Milwaukee Bucks at Portland Trail Blazers Jaime Valdez-USA TODAY Sports

We have never been here before.

The Milwaukee Bucks have been a great team, a contending team, an NBA Finals favorite. We have boasted having an all-time talent in Giannis Antetokounmpo, whose presence was enough to make up for any—almost all—weaknesses that held the team back on the court. Giannis’ recent forays into saber-rattling via sports media weren’t even unfamiliar; the last time it happened, the Bucks landed Jrue Holiday and Giannis signed a super-max extension and Milwaukee won a championship for the first time in 50 years.

But somehow, we’ve never been here before.

Out are Jrue and Grayson Allen, the former a beloved leader and invaluable component of the team’s core, the latter an oft-criticized but highly-skilled guard whose shooting bolstered Milwaukee’s offense. The Bucks also sent out some valuable draft capital to grease the wheels and “get to yes.” Coming in to replace them?

Damian Lillard.

You know, this guy.

Beyond his highlights, Dame is consistently an offensive dynamo. Over his 11 year NBA career, Lillard averages 25.2 points and 6.7 assists on 0.439/0.372/0.895 shooting splits, but he’s somehow so much more than those numbers. Per Cleaning The Glass, Lillard has been in the top 5% (read: best) league-wide in Points Per Shot Attempt...while also maintaining a usage rate higher than 90% of NBA players. He is an incredibly productive scorer, capable of making both open and contested shots from all three levels of the court, and beyond.

But unlike many players (including some former Buck guards near and dear to our hearts), Lillard maintains that level of production in the playoffs. Those Cleaning The Glass numbers from above? They don’t dip very far in the postseason. Dame can not just score it himself, but he’s a capable passer and playmaker, he takes care of the ball and makes good decisions, and while he’ll never be Jrue Holiday on defense, he at least makes an effort.

So why do I say that we’ve never been here before? On the surface, the Bucks followed up their last major trade that added an elite guard three years making a major trade that added an elite guard today. The rest of their core is intact, and while it will be a challenge to adjust around the Bucks’ newest addition it is a challenge worth undertaking.

But we have never been here before, where the team is adding not just the best player from another franchise or a player near the pinnacle for his position, but one of the best players in the entire league’s history. Admittedly, Lillard (33) is not in his physical prime anymore, but this is a far cry from 34-year old Gary Payton for a few dozen games, or 38-year old Pau Gasol, or 32-year old Ersan Ilyasova. The NBA 75 list included both Giannis and Dame, and the two players’ strengths and skill-sets align so well it’s almost that they were custom-built to wreak havoc on opposing defenses together. And now they’ve joined forces, in Milwaukee.

Not a bad way for Jon Horst to answer the concerns posed by the star player, eh?

We should take a moment to truly recognize the audacity that Jon Horst and the front office demonstrated with this move, at this time. With Giannis’ injury submarining Milwaukee’s chances last playoffs and Khris Middleton’s injury tanking them the playoffs before that, simply “running it back” made sense! It was stable! It was safe! Jrue Holiday might have some flaws but his defensive talents and knack for converting some preposterous shots in crunch time were more than enough to think that, as long as they were healthy, the Bucks could compete for a title. But when faced with the path of continuity and the path of huge, extreme risk...Horst chose the latter. Here’s hoping he chose wisely.

With all due respect to all of his current and former teammates, particularly Khris Middleton and Jrue Holiday, since becoming a league MVP Giannis Antetokounmpo has never played with another player that is even close to the same caliber as himself. Dame is that guy. Similarly, Damian Lillard has never played with another player that’s better than him. Giannis is that guy. Middleton becomes the offense’s third option. Brook Lopez gets to focus on blocking shots and flinging open threes. Bobby Portis, Pat Connaughton, and whoever earns the next spot in the wing rotation will continue to perform in their specific roles. Those roles will shift because Damian Lillard is a system-shifting talent, who is good enough to tilt the odds of a playoff series.

The Bucks are more top-heavy today than they were yesterday, but that might be just what they needed to blaze a trail (thanks, Portland!) back to the NBA Finals.