Stretching the Cap: The Bucks’ Risky Bet on Flexibility Over Lillard

To sign Myles Turner, Milwaukee just executed the largest waive-and-stretch in NBA history, and risked everything to convince Giannis to stay. Edition #257

It’s over.

After all that hype, the Lillard x Antetokounmpo era is over.

On July 1st, 2025, Damian Lillard was waived in order to sign Myles Turner, and while Turner was recruited by Giannis himself, he didn’t expect Lillard to be waived in order to sign him. Giannis is very angry and upset, and is not happy with the way the Bucks handled this situation.

The Bucks didn’t just lose Giannis, though. They also lost Brook Lopez. Lopez signed a contract with the Los Angeles Clippers, meaning that he would leave the team after 7 seasons. As teammates, this duo was hazardous, especially on defense. They lifted the Larry O’Brien trophy together.

According to reports, Damian Lillard is “elated” to be waived, and Sam Amick from The Athletic reported that multiple contending teams have called him. Lillard is set to miss most if not all of the 2025-26 season, but it’s not that surprising that he has a good market. His reputation as a scorer and playmaker really puts him above most, and he’s definitely going to be cheaper than the current $56.3 million price tag.

His production? He was already showing signs of age-related decline before the injury. In his two seasons with the Bucks, Lillard averaged 24.6 points on 43.4% shooting. He was also 36.4% from beyond the arc. Lillard was also horrendous on defense, and the cracks really began to show.

The Bucks owe him $113 million. If this stuff hadn’t happened, they would’ve paid him over the next two seasons, but by stretching the contract, Milwaukee will pay it out over five years. This is the largest waive-and-stretch transaction ever. Lillard's contract was actually almost too big to be stretched because the most that a team can pay when they use this strategy would be 15% of a given year's salary cap. In this case, means a max of $23.2 million in 2025-26.

The problem that this combo had is that this Lillard and Giannis combo never really had an opportunity to show what they could really do. Injuries. That’s what happened. But, even when they were on the floor, they could never get something going. The prospectus of this combo was unreal, but we just never saw what they could really do together.

Is it shocking? Absolutely. But there is a reason for it. Because Giannis is considering his future with the Bucks and trying to see if that is his best fit, they needed to do something to make sure that this season wasn’t a lost one, because everything revolves around Giannis in Milwaukee. The Bucks do not want to trade him and start over. The best option in this case would be to go and sign Myles Turner, who, like I said before, was recruited by Giannis.

This is risky, though, because what the Bucks are doing is creating financial flexibility, but it could hurt them in the future in terms of financial flexibility. They tried what the Nuggets did when they traded Michael Porter Jr. and a first-round pick for Cameron Johnson, except the Nuggets created the flexibility for a first-round pick. Front offices are being really lax when it comes to payroll nowadays, especially with the huge restrictions.

This is a desperate move by the Bucks, and at this point, if the Bucks want to retain Giannis, they’re going to have to start the season strong. Personally, I don’t expect Antetokounmpo to get traded in this offseason, but you never know. This offseason has been nuts.

More offseason coverage coming soon.