The Bucks are stuck in a very tough position now, and it all stemmed from their controversial moves last summer. The Bucks' offseason was highlighted by their decision to stretch-and-waive Damian Lillard to sign Myles Turner to a four-year, $108 million contract.
Long-time NBA podcaster Bill Simmons argues that it was worse than the Pelicans trading an unprotected first-round pick to move up for Derik Queen in the draft, a move many think was the worst decision from this past summer. At least the Pelicans got a talented young big out of the deal. For the Bucks to acquire comparable young talent, they would need to pull off a trade involving the older players they currently have.
The Bucks may have it worse than any other team
With Giannis Antetokounmpo's potential trade request looming over the team, the Bucks have hit a doomsday scenario. If Giannis wants out, they could be left with bad contracts for aging players and no draft picks. Hopefully, they recoup some of those losses in the return package for Giannis, but the future looks bleak for now.
The Bucks had high hopes when they made their big offseason changes. Stretching and waiving Lillard was a huge maneuver in itself. It keeps some of Lillard's contract on the books (and salary cap) for the next 5 years despite him not playing any games for the Bucks. But it was understandable as a desperate attempt to secure some level of financial flexibility at a key crossroads.
Unfortunately, the Bucks used that flexibility on a player who hasn't been worth his contract. Myles Turner has been disappointing this season and has failed to earn the coaching staff's trust. Despite being the Bucks' star acquisition of the offseason, he has looked every bit the part of a role player. Turner has failed to unlock any special synergy with Giannis or carry the team in his absence.
It's no secret that the Bucks were taking a huge shot in the dark when they essentially bet future cap space on Myles Turner. Turner hasn't even lived up to the $27 million average annual price tag of his own contract, let alone that amount plus the money that the Milwaukee Bucks will pay Lillard.
The Bucks have been known for taking huge risks with blockbuster trades during Giannis' tenure to increase their championship odds. But their most recent wager has fallen flat and possibly doomed them for the foreseeable future.