The Milwaukee Bucks are currently coming dangerously close to making a mistake the Orlando Magic already made over a decade ago: trying to build around a superstar by making desperate, short-sighted moves, only to end up losing that star and being stuck with the fallout.
Orlando’s infamous decision to trade Rashard Lewis for Gilbert Arenas in 2010 highlights one of the most painful chapters in their history. At the time, the front office thought it was making a bold move to support Dwight Howard’s prime years. Arenas was a player with star power in the league at the time, but he was already on a big contract and clearly past his best days.
The Magic rolled the dice anyway, and Howard asked out a year later. The team was left with no superstar and one of the worst contracts in basketball. Fast forward to 2025, and the Bucks may be headed down a similar road with Giannis Antetokounmpo.
Milwaukee has already taken one major step by stretching and waiving Damian Lillard, which will cost them more than $22 million every year through 2030. It is the kind of decision that teams only make if they feel a lot of urgency to fix things now, even at long-term cost. The front office followed that up by signing Myles Turner, a capable but limited center who may not elevate the ceiling for a Giannis-led team the way Lillard was supposed to.
Milwaukee may be going down the same path Orlando did
The Bucks are obviously scrambling to stay competitive around Giannis. But in doing so, they may be ignoring the reality that he could still ask out later this summer.
If that happens, Milwaukee will be left with a worse core of players and a payroll clogged by the Lillard stretch. It is eerily similar to what happened in Orlando. The Magic tried to keep their superstar happy, and ended up paying the price for years. Now, the Bucks may be the next to learn that lesson the hard way.
Giannis is one of the most loyal players in the league, but that does not mean his patience is infinite. This offseason has already been chaotic in Milwaukee. Brook Lopez is now a Clipper, and Damian Lillard is off the roster as well. Milwaukee is certainly not in the best spot, especially with their latest additions being less-than-slam dunk moves.
That is exactly what the Magic looked like in 2011 when they tried to plug holes instead of laying a real foundation. They made reactive moves instead of proactive ones, and they ultimately lost the only player who mattered.
The Bucks still have time to correct course, but if Giannis requests a trade, it will confirm that Milwaukee has made the same superstar mistake that Orlando already lived through. The names are different, but the mistake is not.