A move of epic proportions could happen soon, with Giannis Antetokounmpo facing an important decision after another playoff exit for the Milwaukee Bucks.

A decade ago, LeBron James shocked the sporting world when he announced that he was leaving the Cleveland Cavaliers and “taking his talents to South Beach.” 

Four years ago, it was Kevin Durant’s turn, as the Oklahoma City Thunder star announced that he was leaving and joining the Golden State Warriors, a team coming off a historic regular season and a seven-game battle against his own team.

Both James and Durant were generational talents who had played years for the teams that drafted and the cities that embraced them. Both James and Durant moved to teams that allowed them to play with multiple All-Star teammates. Both moves were derided at the time they were announced, with fans feeling betrayed and experts saying that the league’s competitive balance had been destroyed. In the end, however, the moves worked out for both stars, as they won multiple titles with their new teams. 

After signing a four-year, $100 million extension in 2016, Giannis Antetokounmpo will not be a free agent until the end of the 2020-2021 season. However, speculation is rife that he already has his sights elsewhere. Milwaukee, however, has one ace up its sleeve that can change Antetokounmpo’s mind: a supermax contract that could pay him $200-250 million over five years. However, signing the contract could present also problems for Giannis. Here are three reasons why he shouldn’t sign the supermax deal this offseason:  

1. A short-term extension would give him more flexibility

Not signing the supermax deal doesn’t immediately mean that Giannis Antetokounmpo is leaving Milwaukee, as he also has the option of signing a short term extension. This would keep him in a Bucks jersey while allowing him to explore other options if the team is unable to compete for a title. A lot can still happen in the offseason, but the early indication is that the 15th overall pick of the 2013 NBA Draft wants to return next season, with a report by Yahoo Sports’ Chris Haynes confirming as much.

“It’s not happening. That’s not happening. Some see a wall and go in [another direction]. I plow through it. We just have to get better as a team, individually and get right back at it next season.” – Giannis Antetokounmpo on rumors of his departure from the Bucks

But despite his loyalty, the reigning MVP is also determined to win a championship. This marks the second year where the Bucks finished with the league’s best record without a Finals appearance to show for it. More playoff exits could change his mind, especially if Milwaukee fails to surround him with enough talent to continue competing for titles. If he signs a supermax contract and the Bucks regress, it could leave Antetokounmpo wasting his prime playing for teams that have no shot at winning a championship. 

During his time with the Bucks, Giannis has proven himself as the world’s best player. It’s time for the Bucks to prove that they can put him in the best position to win a title, and signing a short term extension puts the pressure on the organization to give him a chance to compete each year as he enters his prime. 

2. The Bucks' championship window may have already closed

If Giannis doesn’t end up signing a short-term extension, a reason for that could be that the Bucks’ best chance to win a title may have already come and gone. 

While Antetokounmpo is only just 25 and about to enter his prime, the team has an average age of 29.7 years, the second oldest in the league. Several of their rotation players are either at the back end of their primes or have already started to decline. Players like George Hill (33), Wesley Matthew (33), Ersan Ilyasova (32), Brook and Robin Lopez (31), and Kyle Korver (38) are all in their 30s. Among the Bucks players seeing regular minutes, only Donte DiVincenzo (22) can be considered as young, with their other players also in their late 20s.

In a league that has seen an influx of young talent in recent years, the Bucks have instead gone in the opposite direction. The last two seasons have offered Milwaukee great opportunities to bring home the Larry O’Brien trophy, especially given their dominance in the regular reason. But the team hasn’t been able to translate its success in the postseason, and with an aging roster that includes players with long term contracts, there may be little room for flexibility for a small market team like the Bucks, especially if they sign the Greek Freak to a supermax contract. Instead of competing for titles, staying with the team could mean being mired in mediocrity with an aging supporting cast. 

3. It’s time for Giannis to do what’s best for Giannis

Fans of the Cavaliers might not have liked his departure, but seeing James play with Dwyane Wade and Chris Bosh in Miami unleashed a different version of The King that he never would have realized if he stayed in Cleveland. The same goes for Durant, whose Hamptons Lineup with Steph Curry, Klay Thompson, Draymond Green, and Andre Iguodala was almost unguardable and was a thing of beauty to watch. 

As good as Giannis is now, he can still get better, and the team that could unleash his full potential might not be the Bucks. Imagining him alongside Jimmy Butler and Bam Adebayo with the Heat would probably send the rest of the Eastern Conference cowering into fear, while the prospect of Luka Doncic throwing alley-oops to the MVP in Dallas or him kicking out the ball to a waiting Curry or Thompson with the Warriors are just as tantalizing. Antetokounmpo has already proven himself as a great player, but playing for a team with top-level talent will help him get to a level that he is yet to reach. 

For seven years, he has done what’s best for the Bucks, giving the team a star and a cornerstone to build a team around. He’s given them playoff appearances, great individual performances, and many wins. As he enters his prime, it might be time to think about what’s best for him and which team will make him develop into a better basketball player. As much as he wants to stay with his current team, the answer to that question may not be Milwaukee.