As NBA Media Day kicks off, all eyes are on Damian Lillard and the Milwaukee Bucks. After refusing to sign an extension this summer, Giannis Antetokounmpo seems happy about the trade and has said that he will remain a Buck as long as "we are winning." He mentioned that he is excited to play with a player who is "built from the same cloth". But he also said it does not financial sense for him to sign a contract extension right now.
The MVP becomes a free agent in 2025-26 if he declines his player option. The option is more of an insurance policy for players and will most likely only be used if something horribly wrong happens to the Greek Freak. Until the Bucks traded for Lillard, there were rumors that one of the best players in the NBA might leave via trade request at some point in the future.
With Lillard on the Bucks, the team has a chance to keep the MVP for the long-term future. Still, Antetokoumpo will wait until the next offseason when he can re-sign for $233 million over four years. Ideally, by then Milwaukee will have a championship parade at which to celebrate the signing.
Do the Bucks have a competitive enough roster to keep Giannis Antetokoumpo around long-term?
Obviously, the answer to this question will not be revealed for the two to three years. Still, it seems like the Bucks have a good chance to keep a title-contending roster around Antetokoumpo. Khris Middleton's talent is fading but he doesn't have to be the number two guy on this roster anymore with Lillard taking that role.
At this point in their respective careers, Lillard is more fit to be this kind of player. The All-NBA player is 33 but for the next two years, he should be a solid Robin to Antetokoumpo's Batman. The Bucks will not have the greatest depth but they will be in the conversation to win the title.