Giannis Antetokounmpo Rumors: Bucks 'Cautiously Confident' in Supermax Contract

The Milwaukee Bucks have reportedly gone from being "cautiously optimistic to cautiously confident" that superstar Giannis Antetokounmpo will sign a five-year, $228 million supermax contract extension this offseason, according to ESPN's Brian Windhorst.

Per that report:

"The moves they've made telegraph their confidence. They didn't trade three first-round picks and two pick swaps for Jrue Holiday without insight. There's no question Milwaukee felt the need to make roster upgrades, especially in the backcourt, after last season's playoff disappointment. That is part of a case being made to the reigning two-time MVP. But the Bucks were also acting with confidence that they weren't mortgaging a future without Antetokounmpo. They hope."

But Windhorst added that there are "teams clearly hedging that Antetokounmpo will not extend his deal before the Dec. 21 deadline," including the Miami Heat, Dallas Mavericks, Toronto Raptors and New York Knicks, which all conserved 2021 cap space. 

Those teams aren't alone. Windhorst reported that "for more than a year, teams have been building dossiers, from the role of the closest people in his life—his longtime girlfriend and his brothers—to his admiration for international players who have come over to become successful like him. That and other intel has been collected to use if an opportunity arises."

It's no surprise. The 25-year-old Antetokounmpo is a two-time defending MVP and one of the truly signature talents in the game, combining unique size, athleticism, scoring at the basket and playmaking. While that hasn't translated into a championship—or even a trip to the NBA Finals yet—it could be argued Milwaukee's postseason failures have had more to do with the team's supporting cast than its best players. 

Hence the team's huge overpay for Holiday. The Bucks should be better with a starting five of Antetokounmpo, Holiday, Khris Middleton, Brook Lopez and D.J. Augustin than they were a year ago.   

Will that roster be good enough to convince Antetokounmpo to bypass free agency to sign the supermax?

He would be giving up leverage for money if he signed the extension. Milwaukee can offer him $83 million more in an extension than he can get as a free agent, per Windhorst, but Antetokounmpo's ability to potentially sign elsewhere—or sign shorter deals with the Bucks—offers him the ability to keep the pressure on Milwaukee's front office to consistently build a winner around him. 

If Antetokounmpo is happy with Milwaukee's offseason, perhaps holding onto that leverage loses its relevance. We'll have a better idea by Dec. 21.