The Milwaukee Bucks are at an interesting crossroads. On one hand, they are yet again a top seed in the Eastern Conference, in large part due to another MVP-caliber season from Giannis Antetokounmpo. On the other hand, anyone who has watched this team can see that something has been a bit off.
The Damian Lillard acquisition hasn’t lived up to the hype. Going from Adrian Griffin to Doc Rivers didn’t fix their season trajectory. Khris Middleton and Brook Lopez are starting to look their age. Outside of Bobby Portis, the bench hasn’t been all that impressive. More than anything else, the Bucks have never quite found their groove.
And now, they have an excuse if things don’t work out in the postseason. Antetokounmpo is sidelined with a calf strain and "there's some real doubt" he'll be ready for the start of the Bucks' first-round series against the Indiana Pacers, per The Athletic's Shams Charania. Even if he's ready, there’s no telling if he will be at 100%. Calf strains are delicate injuries, even more so around the postseason (just ask Kevin Durant).
If the Bucks don’t succeed, they can attribute it all to bad luck health-wise and run it back next year. But would that be the brightest idea? Even if Giannis’ latest injury is a valid excuse, it's not like this season was going swimmingly before he got hurt. The Bucks never figured out their rotation despite having a talented and battle-tested roster. There were flashes, as they had impressive blowout wins over the Oklahoma City Thunder and Boston Celtics, but it never turned into any consistency. Giannis’ injury, plus his ambiguous recovery time, further limits the Bucks’ chances of going on a deep postseason run.
In all fairness, they’ll only have to cross this bridge if they come to it, but if this season goes down in flames - healthy Giannis or not - the Bucks have to think about whether they want to keep this core intact. This was their worst regular-season output since the 2017-18 season. They were at a 52-win pace during the shortened 2020-21 season, and their core guys are not getting any younger. Lopez is 36 years old. Lillard will turn 34 in July. Middleton will turn 33 in August.
A tumultuous season coupled with an aging supporting cast casts a murky shadow on the Bucks’ future with their current core. On the plus side, Antetokounmpo is only 29 years old, and the Bucks have him under contract for at least three more seasons. They have time to figure this out. What they don’t have is the assets to retool with better players than what they have now.
They spent the majority of their future assets getting both Jrue Holiday and Lillard and are fresh out of first-round picks to offer for the time being. If they decide that this core can’t get them another championship, the only way they can feasibly bail themselves out is to trade their core pieces outside of Giannis for similar-caliber players who might fit better alongside Antetokounmpo.
Who that might be is anyone’s guess, but the Bucks have shown that they are willing to go the extra mile to improve their ceiling. While an overhaul sounds drastic, this season has not gone the way the Bucks hoped. Do they really want to try running it back? They already tried making a change at head coach. They've tried it twice! The fact that their ceiling failed to rise despite having three different head coaches over the span of a year indicates that the coach isn't the sole problem.
Overhauls are tricky, and most NBA teams view them as a last resort to salvage what they can of their closing title window. When it was clear that Rashard Lewis and Vince Carter could no longer hold their own, the Orlando Magic tried replacing them in 2010 with Gilbert Arenas, Jason Richardson and Hedo Turkoglu in the hopes of surrounding Dwight Howard with a better core. While it didn't work, the Magic at least went down swinging.
The Cleveland Cavaliers did the same thing in 2018 when it was clear their team makeup post-Kyrie Irving trade wasn't working. It's debatable as to whether acquiring George Hill, Jordan Clarkson and Larry Nance Jr. truly made them better, but the fact remains that they made the NBA Finals anyway in their last year with LeBron James.
If Milwaukee decides that go the overhaul route, it will admittedly be a bit difficult. Not only are the Bucks’ best players declining, they are getting paid a lot of money. With the Bucks being a second-apron team, they also have the disadvantage of not being able to combine salaries to trade for someone who makes more money.
For all the criticisms the Bucks have received over the years, they have at least been willing to confront the elephant in the room. When it was clear that Eric Bledsoe wasn’t working out for them, they upgraded to Holiday. When it was clear that their halfcourt offense was limited with Holiday as their point guard, they went out and acquired Lillard. They didn’t get the results they wanted, but they at least tried to fix what was an obvious problem.
If they fail again, they might have to confront a new elephant in the room: dismantling the core outside of Giannis. Doing so is not a foolproof option—in fact, it's pretty much the nuclear option—but it might very well be their best one at this point.
