When Giannis Antetokounmpo’s name is mentioned, it’s hard not to think of his dominance with the Milwaukee Bucks. A two-time MVP and 2021 NBA champion, Giannis has already reached the pinnacle of the NBA. But after the Bucks’ third consecutive first-round playoff exit, reports suggest Giannis is considering life outside Milwaukee. The thought of him leaving is jarring, especially considering how integral he’s been to the team’s success.
But there’s a parallel story in NBA history that serves as a cautionary tale: the career of Dwight Howard. Like Giannis, Dwight Howard was once an unstoppable force in the NBA, a player with the physical tools to dominate.
The Pressure to Win: Can Giannis Learn from Howard’s Mistakes?
After years of falling short with the Orlando Magic, Howard arrived in the Los Angeles Lakers in 2012, determined to finally capture a championship alongside Kobe Bryant. Things didn’t quite go according to plan, though. The Lakers underperformed, and Howard’s championship aspirations were crushed. It wasn’t until he returned to the Lakers in 2020, as a role player, that he won his first title.
Howard had this to say to Giannis:
Don’t leave Giannis coming from someone who been there
— Dwight Howard (@DwightHoward) May 12, 2025
Howard’s journey shows that the exit for a title can be far more complex than one would have hoped. What Howard learned was that his pursuit of the title came at a very high emotional price, as he left behind his legacy in Orlando for unfulfilled glory in LA.
Giannis is under the same pressure to win a second championship. As understandable as it is he’s thinking about his future with the Bucks, it’s also important to remember Howard’s career. Giannis, unlike Howard, has a championship with the Bucks already. Leaving Milwaukee to go be part of a “super team” elsewhere may yield short-term success at the cost of his long-term legacy
The Unseen Cost: The Impact of Leaving
Howard’s exit from Orlando affected his legacy. Even though he did eventually win his title with the Lakers, it was not with the same pride and gratification he could have had if he had stayed with the Magic. For Giannis, leaving the Bucks could have the same effect on his relationship with the city and the fans.
The emotional cost of abandoning a franchise that believes in you is one that cannot be measured in rings alone. Giannis has the unique opportunity to stay and build something truly special in Milwaukee, or potentially risk his relationship with a city that’s been with him every step of the way.
Giannis is at a crossroads. His decision will define his place in NBA history. Should he chase more rings with another team, or remain loyal to the franchise that helped him become a star? The legacy he leaves will depend on the choice he makes now