One of the bigger stories that occurred in the NBA this summer was the unexpected waiving of Damian Lillard by the Milwaukee Bucks. The 36-year-old superstar was sent packing, which cleared up room for the Bucks to add Pacers star Myles Turner alongside Giannis Antetokounmpo.
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The move, albeit shocking, still made sense. Dame had torn his Achilles tendon in the playoffs and was most likely going to sit on the bench for the majority of the 2025-2026 NBA season anyway, with a ton of guaranteed money still going his way. Dame Time has since signed a new contract with his old squad, the Portland Trail Blazers. Everyone seems happy about that.
Some people are not looking at the potential 4D chess that the Bucks could be playing. But Brian Windhorst is. The famed analyst and insider gave his thoughts about the move on the latest edition of NBA on ESPN.
Windy began by recalling how he felt in the moment when he broke the news that the Bucks had waived Lillard. “I, in the moment, said, ‘It’s like mortgaging your mortgage to buy a sports car.’ I still don’t like it,” stated Windy. That said, he has since theorized an elaborate multi-year plan involving Giannis’ future that Milwaukee is potentially eyeballing.
“I’ve talked to people across the league and thought more about it. While I don’t necessarily think it’s the primary reason, I think that maneuver was an elaborate hedge on what Giannis wants to do,” he predicted.
This might seem like a wild hypothesis, a common scheme of Windy’s. But he broke it down in a way that actually makes a lot of basketball sense, especially with how tricky the business aspects can be. The move for Turner plays well for Giannis and company now and gives the Bucks more trade value if they need to deal the Greek Freak away.
“Yes, ideally, what you want is Giannis to return, be fully bought into the season. Have a guy that fits alongside him that can stretch the floor and protect the rim,” Windhorst said. “That’s a lot of value. It’s you sending a message to Giannis that we scraped the bottom of the barrel.”
Windy then mentioned Bucks GM Jon Horst’s comments about the situation.“Jon Horst wants it on the record that they did everything they possibly could do. Why? I think because the Bucks can try and do their best with Myles Turner and having waived Dame Lillard.”
“If, at some point in the next year, you trade Giannis and you start a rebuild, you can’t really start a rebuild with Dame Lillard on your roster. Because he has no trade value with a torn Achilles tendon [and] owed $100 million, and you can’t waive and stretch him in January,” Windy explained.
Windhorst put it bluntly, “So you waive and stretch him now, then you use that money to acquire an asset that you can either play or, if you have to, trade.”
All of this does make sense when you put it side by side. Giannis expressed interest in hearing offers from other teams this offseason after the Bucks’ third straight first-round exit. Milwaukee showed that they made an effort to keep the future Hall of Famer, but if things don’t pan out, they have the tools necessary for a rebuild.
Again, it’s Windy looking at the business aspects of the game the way no one else is. Will this prediction come true? Not necessarily. However, every franchise should be thinking about the long term. If Giannis doesn’t fit into that plan, pack your bags, big man.
