Weeks After His Warning for Giannis Antetokounmpo, Dwight Howard Discusses His Regret About Leaving Orlando

The biggest domino of the 2025 NBA offseason is Giannis Antetokounmpo’s future with the Milwaukee Bucks. Following yet another disappointing first-round exit, uncertainty has begun to brew in the Brew City. NBA legend Dwight Howard issued a warning to the Greek Freak when the rumors originated. Weeks later, he remains firm in his stance.

Damian Lillard’s torn Achilles injury guarantees that the Milwaukee Bucks will suffer another season outside of title contention. Antetokounmpo has made it clear that he isn’t in the business of simply being competent. He wants to win championships, even if that means elsewhere.

Every NBA competitor can understand the competitive fire that Giannis possesses. Howard, on the other hand, can relate on a personal level since he went through a similar situation. On May 12, he took to X to give Antetokounmpo advice on what he should do.

“Don’t leave Giannis, coming from someone who been there,” Howard said.

Howard forced his way out of the Orlando Magic in 2012. It’s clear Howard doesn’t believe he made the right decision in hindsight. Following his post, he didn’t provide more reasoning behind his warning. Well, that was the case until his appearance on the Club 520 Podcast.

“One of the craziest things I did was just leaving Orlando. Not knowing what I had until it was really gone,” Howard revealed. His pursuit of championships led to his deepest regret of his NBA career. He implores Giannis not to fall victim to the same mindset.

“I just tell Giannis, you are Milwaukee. He already won, what else does he have to do? If he stays, he’s going to get a statue. Thanasis will get a statue if he stays,” Howard said.

Howard struggled to find another place to call home once he parted ways with the Magic. In 10 seasons after leaving Orlando, Howard played for six teams. Four of those were one-year stints. That doesn’t mean Antetokounmpo will follow the same trajectory, but the probability is there.

Giannis doesn’t have to look farther than his teammate Damian Lillard. The nine-time All-Star reluctantly left the Portland Trail Blazers to prioritize winning. His two seasons with the Bucks have been utter failures with that goal in mind.

The moral of the story is that championships aren’t the sole indicator of a legendary career. The value a player has to a franchise speaks volumes to their legacy. Howard believes Giannis won’t be the only recipient as his brother, Thansis, will reap the benefits too.

The possibility remains that Howard’s comments may go over Antetokounmpo’s head. Regardless, it doesn’t change the fact that the grass isn’t always greener on the other side.