There is a lot of uncertainty surrounding Giannis Antetokounmpo's future with the Milwaukee Bucks. The two-time MVP has proven to be one of the NBA's most loyal stars. So far he has spent his entire 10-year career with the small-market team that drafted him. However, Antetokounmpo wants to win more championships, and could take his talents elsewhere if the Bucks are unable to give him that opportunity.

Much about The Greek Freak's future could be learned in the coming weeks. Antetokounmpo becomes eligible to sign a contract extension with the Bucks on Friday, September 22nd. He's under contract for two more years with a player option for 2025-26, but the clock is ticking towards his eventual free agency.

Antetokounmpo appears to be growing more impatient by the day, so it leaves fans wondering: Will the former NBA Finals MVP sign an extension to stay in Milwaukee, or be suiting up for a new team sooner rather than later?

Giannis Antetokounmpo's career

There is a case to be made Antetokounmpo is the best player in the world. He already has one championship, two MVPs and seven All-Star appearances to his name. He is only 28 years old, and averaged career-high 31.1 points per game last year last season.

While Antetokounmpo does have an NBA championship ring, an accolade that has eluded many great players before him, he's not satisfied with one.

Antetokounmpo is entering his 10th season, and has already put a lot of miles on his body. Players who rely so heavily on strength and athleticism often see regression in their game before they are ready to admit it, so Antetokounmpo's championship window may be closing quicker than you think.

Still, there are few players—and maybe none—any team would want more than Antetokounmpo right now. He is one of the most dominant forces in the game, a two-way force who can play alongside anyone. A Defensive Player of the Year award winner, Antetokounmpo fills a lot of gaps on the defensive end. He can play in the paint or out on the perimeter. His versatility has helped the Bucks reach heights they hadn't seen in decades. His malleable play style could also work alongside other superstars if Antetkounmpo decides to move on from Milwaukee..

Giannis Antetokounmpo's current contract

The two-time MVP has talked before about spending his whole career with the Bucks, but his desires have seemed to shift in recent months. Winning is clearly priority number one for Antetokounmpo. If Milwaukee, already one of the oldest teams in the league, isn't a top-tier title contender going forward, he's straight-up said he'd be willing to leave.

The Bucks are safe for now unless Antetokounmpo requests a trade. While that seems unlikely, you never know these days, as superstars are asking out more frequently than ever.

Antetokounmpo signed a five-year, $228 million dollar contract extension with the Bucks in 2020. It was the largest in league history at the time, and he's about to begin year three of the deal.

State of the Bucks' roster

The Bucks are familiar with their franchise cornerstone jumping ship after bringing a championship to town. Kareem Abdul-Jabbar, arguably the greatest player of all-time, played in Milwaukee from 1969-1975. He brought home the team's first championship in 1971, but left for the big market Los Angeles Lakers—a team built for consistent winning—just a couple of years later.

The Bucks don't want to see the same outcome happen with their greatest player since Abdul-Jabbar. They must do whatever Antetokounmpo asks of them, and that seems to be ensuring they have enough talent on the roster to help him hoist another Larry O'Brien Trophy.

That will be easier said than done for Milwaukee. The team is fresh off of a disappointing first-round exit in the playoffs, and improving the roster comes with challenges. Khris Middleton, Brook Lopez and Jrue Holiday have already proven they can win a championship, but are only getting older. You aren't likely to see any individual improvements from any of those players, and their pricey veteran contracts severely limit the Bucks' flexibility.

Middleton's contract is very steep at over $30 million per year, and he has struggled with injury issues recently. Lopez's contract of two years and $48 million is rather large for a 35-year-old. That is a lot of money tied up into arguably Milwaukee's third and fourth-best players, meaning the team can't afford any big-name free agents.

Holiday also has a contract that is north of $30 million per year. He has a player option for next season, and the Bucks may be at risk of losing him. The team is also limited in what it can trade away to acquire talent. Due to previous trades, the Bucks don't have a tradeable unprotected first-round pick until 2029. They can also trade pick swaps in 2028 and 2030. Those picks are awfully far out and might not be the most appealing assets to potential trade partners, meaning Milwaukee may be hard-pressed to acquire a contributor through the trade market, too.

Giannis Antetokounmpo's contract extension

On multiple occasions this offseason, Antetokounmpo has made it blatantly clear that winning is the priority. If the Bucks can't put together a winning team, The Greek Freak is at the point where he will be fine moving to another contender.

On September 22nd, Antetokounmpo will be eligible to sign a three-year, $169 million extension with the Bucks. The deadline to sign this extension is October 23rd, 2023, which is the day before the start of the regular season.

It is highly unlikely Antetokounmpo will sign an extension. First of all, opting against it will allow him to see how the Bucks roster progresses and develops over the coming year. Secondly, and just as importantly, Antetokonmpo will have the option to sign an even more lucrative extension next summer. If he waits until 2024, he can sign an extension worth roughly $234 million over four years.

Antetokounmpo will be playing in Milwaukee for the foreseeable future. But that could change in the blink of an eye, especially in a player empowerment era that has seen so many superstar trade requests. Regardless, the Milwaukee needs to do everything possible to keep Antetokounmpo happy, and in a Bucks uniform for life.