After an injury-riddled season to key pieces within their starting lineup, the Milwaukee Bucks finished with a bleak 32-50 record and missed the playoffs for the first time in a decade. 

Yet, their most important task this offseason is ensuring they can keep Giannis Antetokounmpo in Milwaukee. Antetokounmpo is set to make over $58 million in the final guaranteed year of his contract before his player option for the 2027-2028 season. 

Antetokounmpo has expressed his desire to stay in Milwaukee for “many more” years, but Bucks co-owner Jimmy Haslam’s acknowledgement that moving him before the draft “is a natural time” suggests that his time in Milwaukee could end quickly. 

With Antetokounmpo eligible to sign an extension on Oct. 1st, here’s how the Bucks can help convince him to stay. 

The Bucks enter this year’s draft with a lottery pick for the first time since 2016, but they will need to land an important piece to convince Antetokounmpo they are in a win-now mode. 

Who better to trade for than Trail Blazers guard Jrue Holiday? The former Buck was part of that 2021 championship team and is a proven playmaker at the biggest stage. 

The six-time All-NBA Defensive selection is known for his suffocating perimeter defense and two-way play as a floor general. 

Holiday has an extra year on his contract with a $37 million player option. Add in Kyle Kuzma and his $20 million expiring contract, and the Bucks can also free up space. This trade has a huge upside for the Bucks and gives Antetokounmpo a teammate he trusts. 

Antetokounmpo needs a reliable second option in the backcourt that can consistently step up even when he’s off the floor. 

That potential second option is Miami Heat guard Norman Powell. While the Heat remain heavy favorites to trade for Antetokounmpo and try to resign Powell in the process, Antetokounmpo's hesitation can thwart their plan, as the Heat more than likely don't want one without the other. 

Powell earned his first all-star selection this past season by averaging 21.7 points and shooting 41.8% from deep. 

Outside of his catch-and-shoot abilities, Powell is also a terrific finisher at the rim and can provide the absence Antetokounmpo has been looking for in his rotation. Powell has until June 30 to sign any extension with the Heat.

While the Bucks need additional pieces to convince Antetokounmpo they are capable of winning, they also have valuable pieces in their rotation. 

Despite battling injury most of the season, Porter Jr. continues to prove his worth as a scorer from all three levels. Porter Jr. is also their elite defender who can get into passing lanes and use his quick reach. 

Ryan Rollins also found his footing with the Bucks, averaging 17.3 points and shooting over 40% from deep. One of their few guys who stayed healthy all year, Rollins was a huge factor that helped the Bucks emerge as one of the top three-point shooting teams. 

Rollins can emerge as their primary wing shooter if he picks up his player option. 

The most important thing for the Bucks is their new head coach in Taylor Jenkins.

A proven winner who compiled 250 wins with the Memphis Grizzlies and earned the No. 2 seed in back-to-back seasons, Jenkins was also an assistant coach for the 2018-2019 Bucks team that won 60 games and made it to the conference finals. 

The 41-year-old already has experience with Antetokounmpo and is a big change from the drama that ensued from former head coach Doc Rivers.