The Bucks are holding a mountain of Giannis Antetokounmpo debt because they didn't know when to let go

Giannis Antetokounmpo hasn't officially demanded a trade. According to recent reporting, he and his agent are just "having conversations" with the Bucks about where Milwaukee remains his "best fit." 

The "fit" euphemism always makes me laugh. Teams have been saying for the last half decade that Russell Westbrook doesn't "fit" here or there. Just say what you really mean. You think Westbrook stinks. 

Apologies for the Westbrook stray, but now we're going to do the same thing with Giannis and the Bucks, who would, magically, be a fine "fit" for Antetokounmpo if they didn't stink. But they do. Which is fine. It's how it goes most of the time. You have a good run. Win a championship if you're one of the lucky ones, as Milwaukee was after a lot of the league got COVID and Kevin Durant's toe landed on the line. Eventually, you can't keep it going anymore. As the old Anheuser-Busch campaign warned: Know when to say when. 

In this case, "when" would've been this summer. The Bucks, who had done everything in their power to put Giannis in a position to win by trading for Jrue Holiday and then Damian Lillard, could have, and should have, put the punch down and taken an Uber home. That would've been the responsible thing. Instead, they tried to keep the party going and wound up drunk dialing Myles Turner, who woke up the following morning with a four-year, $107 million contract. 

To pay for it, the Bucks waived Damian Lillard and stretched the $113 million left on his contract over the next five years. Yes, you're reading that correctly. The Bucks are going to be paying Lillard more than $22 million annually for the next half decade to not play for them. Add Turner's money to the ledger, and that comes out to damn near a quarter billion dollars for a younger Brook Lopez. 

Sure, they owed Lillard the money either way. But biting the bullet and just letting his contract run out was going to clear him from their books in 2027. Perhaps by next year they would've been able to trade him on an expiring deal. Twenty-two million bucks is a massive amount in today's financial landscape where good players no longer make ridiculous money. You could get two Davion Mitchells for that. Or Herb Jones and Aaron Wiggins. Or Nickeil Alexander-Walker and Mark Williams. Or five Jose Alvarados or Collin Gillespies. 

In real terms, that's what Lillard is going to cost the Bucks for the next half decade, on top of the $26.75 million per year or Turner, who never even should've been part of the equation. We're literally talking a max salary that those two will eventually be costing the Bucks in money they didn't have to pay, that they signed up to pay on the hope that the mere appearance of aggression would be enough to tie up Giannis by his homegrown heartstrings. 

It's not hindsight to say this was a desperate move. It's also not strong enough. It was outright delusional to think that the calculus of adding Turner, while subtracting Lillard, had any chance of equaling anything close to a contender. The "East is wide open" rationale was laughable. Yes, the East is wide open for good teams, but the Bucks were never going to be that. Just look at the roster and put it up against the most collectively talented time in NBA history. Kyle Kuzma? Kevin Porter Jr.? A.J. Green? Bobby Portis? Ryan Rollins had to come out of nowhere just for the Bucks to feign relevancy for a few early weeks. 

This was always headed here. Giannis has left enough "I only care about championships" bread crumbs to know he's been soft launching an exit for a while. He's never come right out and said as much, and in fact he still hasn't, because it's hard to do the dumping. Nobody wants to be the bad guy. So he's been pulling the poker play where you know your next move but ponder it for long enough to appear unsure.

Giannis Antetokounmpo mock trades: What potential offers from Knicks, Lakers, Warriors could look like

Sam Quinn

This is all a dance. Giannis is as good as gone. It's only a matter of when and where he's going. It sucks for the Bucks, who can't ever be accused of taking their superstar for granted. They sold out for Giannis. They didn't dip their toe in any two-timeline waters. They don't own a first-round draft pick free and clear until 2031. They never once hesitated to pull the boldest and oftentimes quickest of triggers -- even at the risk of ultimately shooting themselves in the foot. 

Having one of the best players in the world on your team is tricky business. A good problem, you might say. You are basically obligated, even if means going deep into debt, to make as much hay as possible while the sun is out without ever actually allowing it to set. As long as a player like Giannis is on your team, you aren't allowed to call it a day. Be happy with the good work you got done in the limited time you had. No, you are expected to keep working for him. Keep trying, however futilely, to push the sun back up into the sky. Keep fending off the inevitable dawn of a new day. 

The Warriors are in this spot with Stephen Curry right now. They don't want to mortgage their future, but it feels irresponsible, almost athletically inhumane, to allow a player of his caliber to die on the vine of mediocrity. Giannis isn't Steph, but in terms of what he has meant to Milwaukee, he's not far off. A homegrown MVP who put a small market on the game's biggest stage and delivered a 50-point masterpiece to close the curtain on the franchise's first championship in 50 years. 

You can understand the desperation to keep a player like that from leaving. It's a tale as old as time. The guy buying jewelry he can't afford for the woman he's scared of losing. But sometimes you have to know when it's time to let go. For the Bucks, that time was this summer. The Holiday trade got them a title. The swing for Lillard was worth the risk. But that's where it should've ended. Pulling Doc Rivers off the air was desperate. Signing Turner for, effectively, $220 million was delusional. 

Because in the end, this was always headed here. The only way Giannis was going to end his career with the Bucks was if he decided he valued playing for one franchise over winning a second championship. It wasn't going to swing on Myles Turner, who, in one of the least surprising developments ever, is about to become a nine-figure piano tied to the foot of a team in rebuild. 

It sounds ridiculous to even have to point any of this out. It seems, and seemed, so obvious that the Turner-Giannis pairing, even in its best-case scenario, was never going to move the proverbial needle. At least not enough to justify the significant risk involved. But franchises beholden to once-in-a-generation talents are uniquely positioned to lose sight of reason. That cannot be overstated. The Bucks went blind this summer. They couldn't, or maybe in some sense wouldn't, see the very clear writing on the wall. Giannis is leaving. But the debt they racked up trying to keep him, that isn't going anywhere.