The Milwaukee Bucks have suffered back-to-back first-round playoff exits. Damian Lillard's addition didn't have the galvanizing effect the front office had hoped for last season. Now, the Bucks enter the new season with their sights again set on contending for a championship and erasing the memory of the past two seasons.
Giannis Antetokounmpo has vocalized his desire to contend at the highest level. He wants to win championships and build his legacy. If the Bucks fail to make a legitimate postseason run for the third straight season, Giannis' time in Milwaukee may have run its course.
The Bucks roster is aging, and the front office has few tradable assets and minimal cap space. It can only be done with a hard reset if they need to change direction. Giannis can't be expected to waste multiple years of his career waiting for that rebuild to pay dividends.
According to ESPN's Shams Charania and Brian Windhorst, multiple teams around the NBA have begun monitoring Giannis' position in Milwaukee, specifically his commitment to remaining with the franchise.
"They are very closely monitoring how this situation goes in Milwaukee," Charania said on Tuesday's episode of First Take. "How he looks. How he plays."
Windhorst then built off Charania's comments, noting how all eyes will be on Doc Rivers' team throughout the upcoming season.
"These are the conversations Shams and I have when we talk to people in the league," Windhorst added. "When Shams and I are talking to people in the league, this is what they're talking about. They're talking about what's going to happen with Giannis. What's going to happen with the Bucks. How are the Bucks going to be this year? Are they going to be good enough where Giannis is going to stay committed?"
Milwaukee is reaching an inflection point. Khris Middleton isn't the same elite supporting star he once was. Brook Lopez is deep into the final act of his career. Damian Lillard isn't getting any younger, either. To further compound their issues, they don't have much in the way of young talent with All-Star upside.
Giannis can't be expected to stick with a team in decline. The only way to appease him is to remain competitive and embark on a deep playoff run. Another first-round exit would be a hammer blow to this version of the Bucks.
Nevertheless, Giannis is under contract with Milwaukee until 2027 at the earliest. As such, the team does have a certain degree of control over his immediate future. But if a hard reset is needed, Giannis would expedite that rebuild on the trade market. It might not be easy, but his future is far from guaranteed in Milwaukee.
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