It is difficult to establish how the Milwaukee Bucks went from perennial Eastern Conference favorite with lovable stars and supporting pieces all winning a championship together to cement the legacy of an all-time great … to whatever is going on now. It may, one day, require academic investigation.

Giannis Antetokounmpo, one of the greatest players in the recent history of basketball, is all-but-guaranteed to be traded this offseason given his signals that he will not sign a contract extension. The animosity between the Bucks and Giannis is one of the more dramatic divorces in my sports memory, and it is shocking to see how bad this has gotten since 2021, when it seemed like everything pointed to the two laughing by the fire in matching armchairs into their golden years. That uh, does not seem like it will be happening. Someone cancel the armchair order from Sears.

As with many of the great disasters in sports, Giannis’ split from the Bucks was an institutional failure rather than the actions of a single party. Antetokounmpo has done a great deal to complicate things, such as wishy-washy rhetoric about his wishes and a demand to play out the end of a meaningless season, which was the straw that broke whatever camel’s back anyone was still on. 

But it was also a failure by the Bucks in rational planning, often prioritizing temporary expedients to appease Giannis or adopting reward-based team building rather than proactively and aggressively upgrading the roster. And while there are infinitesimal little moments I could point at to illustrate this issue, I think three moments in the past three years really shine through.

Conspicuously absent from this list is “the Damian Lillard trade,” something I think was aggressive and defensible at a time when the Bucks vibes were at an all-time low. Many will remember that as the trade that accidentally redirected Jrue Holiday to the Boston Celtics, a move which basically won them a title, but I don’t think that qualifies. Onward with only the true disasterclasses!

1. Khris Middleton’s 2023 contract extension

First, an appetizer. This is the type of reward-based contract behavior that NBA teams must avoid if they want to stay relevant in the era of limited financial flexibility. Middleton was a huge part of the 2021 championship roster, but had an extremely up-and-down 2022 and 2023, riddled with injuries and myriad signs that he was not the player they once relied on — his scoring dropped from 20 to 15 points per game, and while he played well in the playoffs, he was unavailable for huge chunks of the season. 

However, the Bucks did not wish to break up their championship roster so soon, rewarding Middleton for his many years of service with three more years and $93 million with a player option on the end. A stable-but-not-resurgent 2023 led to a fall off a cliff in 2024, which forced Milwaukee to trade one of their only remaining first-round swaps to get off Middleton’s deal for Kyle Kuzma, who isn’t good. 

These are the kinds of contracts that kill your franchise. Paying a physically declining third-to-fourth option almost $100 million into his mid-30s is like the NBA equivalent of drinking cyanide and chasing it with a lime. They “did right” by Middleton, but that kind of calculus doesn’t scour anymore — the cap is too restrictive, and stars are too expensive.

2. Firing Adrian Griffin and hiring Doc Rivers

We need to quickly check ourselves before we wreck ourselves here. History will remember that the Bucks fired Griffin 43 games into his coaching tenure when the team was 30-13; an unprecedented move. Nobody had ever fired a rookie head coach with that level of success during his first season. But it was not a completely unexpected move in the moment.

The Bucks vibes were a disaster all season, with the players reportedly resisting Griffin’s schematic adjustments with heads butting everywhere you looked. It was not necessarily true at the time that firing Griffin was a totally indefensible choice, as insane as it seems right now.

But it was emblematic of the kind of business Milwaukee was running: players, by which we all mean Giannis, were running the show. The front office and coaching staff were totally captive to the whims of their superstar, which extended into Rivers’ tenure. Myles Turner (who we are getting to don’t worry) recently discussed the lack of discipline on the Bucks last season, citing Antetokounmpo’s behavior as particularly shocking. 

The firing of Griffin showed a willingness to impulsively change course and exposed a totally spineless front office that was so terrified to lose Antetokounmpo that they could not stand up to him. It was their very fear of ruin brought about the end times. 

3. Damian Lillard waive-and-stretch into Myles Turner “supermax”

It is possible, albeit not confirmed, that the Damian Lillard-Myles Turner situation is the worst single transaction in NBA history. If you wish to cry hyperbole, please find me a worse one. When this is your move, just trade Giannis!

For those who don’t know the nitty-gritty, here are the basics: last summer, with an injured Lillard and a limited contention window with Giannis, the Bucks waived him and stretched his contract over the next five years for basically the maximum allowed amount: 22 million a year, completely untradable and unrecoverable, counting against the salary cap for five years. With their newfound “cap space” they signed Myles Turner to a four-year, $107 million contract to try and win now.

Turner is a decent stretch-five/rim protector whose scoring shot up in 2022 but has been declining closer to his career under-14 points-per-game. He was coming off a great season with the Indiana Pacers, and four-for-107 was a fine deal for that player.

But it’s not four-for-107! Since they have the ghost of Damian Lillard making five-for-113 on top of it, they essentially signed Myles Turner, a fine player, to a four-year, $220 million contract, $113 million of which they literally cannot trade no matter what. At the moment, many Bucks fans talked themselves into it as a risky but necessary move given they were already in a financial straitjacket. What’s another strait on a straitjacket? Conversely, I did not talk myself into it, and I would guess most Bucks fans have squarely talked themselves out of it. Turner had a terrible 2026, and has three more utterly unavoidable years left on the books with a hilarious fourth year of ghost-Lillard after that. 

Acts of congress may be required to limit those kinds of moves in the future. It was the ultimate panic, suggesting that Giannis had made it fairly clear to the Bucks that if they couldn’t contend he would leave. Facing the prospect of losing their best player since Kareem Abdul-Jabbar (who they also lost) the small-market Milwaukee moved heaven, earth, and Damian Lillard to make … something happen. That something itself turned out to be losing Giannis, their greatest fear, their fate, which they tried to run from but couldn’t escape. In the end, the Greek Freak, centerpiece of a Greek tragedy, was already gone.

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