Two NBA legends, two Florida residents, and two big-time house flippers. Only one is doing it better, though. Michael Jordan and Shaquille O’Neal’s individual property portfolios are not to be scoffed at. While Jordan invests in making properties to reflect himself, Shaq’s tastes have evolved. It’s also how O’Neal has bought and sold more homes than MJ. Famously, each had a crowning jewel in their real estate collection. O’Neal managed to sell his with little difficulty, but Jordan’s home has acquired the dubious reputation of the unsellable mansion.

That could change after a 12-year wait. MJ’s Chicago home has gone under contract for a potential sale. It begs the question, did Shaq’s home sell fast because it’s better?

Michael Jordan’s disadvantage is where he was

When rookie Shaquille O’Neal signed with Orlando Magic, he went househunting. He settled on a cool lakefront property in Windermere. He paid $3.95 million in 1993 but over the years personalized and expanded the property.

Around the same time, the reigning champ, Michael Jordan, began building his home in Highland Park. He reportedly spent $50 million personalizing it to his specific tastes and the imposing #23 gates. He listed it for sale in 2012 for $29 million but has only got a prospective buyer in 2024.

Meanwhile, Shaq listed his recognizable blue-roofed home for $28 million in 2018. In three years and a decent profit, he sold it for $11 million in 2021. The location plays a big part in this deal.

From the time O’Neal descended until today, the mansion’s location remains “the most sought after” in Central Florida. Along with the view of Lake Butler, it is situated in the gated neighborhood of the exclusive Isleworth Golf & Country Club for the rich and famous.

Jordan, however, picked the suburbs of Highland Park 30 minutes from the United Center. His home is located near a busy set of railroad tracks in an area where homes are valued at not over $5 million. He now resides in Jupiter, Florida, but he remains a registered property owner in Chicago.

Shaquille O’Neal gets his money’s worth

With a 26,000 sq. ft. home over a sprawling 56,000 sq. ft. property, Jordan’s got the bigger home. Comparatively, Shaq owned 31,000 sq. ft. of living space on 35,000 total sq. ft. in Windermere. Both hardly had a permanent residence in either mansion. Shaq still travels between his homes in Atlanta, Las Vegas, Florida, Texas, and California. Jordan hasn’t lived in Chicago since 2012.

O’Neal was paying an estimated $137,000 in taxes over his original Florida home along with his other properties. But he does get uses out of them. Meanwhile, billionaire Jordan has to shell out $135,969 annually on a home he doesn’t use.

The local county valued Jordan’s property over $4 million. This means if the deal does go through, the new owner’s taxes would like to double at today’s rate.

Superman vs. Air Jordan, which one is erasable?

Between both, Shaq gets to boast he had the most expensive home in a hot buyer’s market. From the 2018 listing price, the $500 million rich O’Neal slashed the price three times and went through multiple realtors. The fifth agent was the charm, finally selling the house for $11 million. Although it was well below the asking price, it was a record-breaking sale in Windermere and Orange County.

The 12-bedroom, 15-bath home has access to the golf course nearby and a water park feature. With higher ceilings to accommodate 7-foot giants, the home has a 6,000-square-foot indoor basketball court that reads “Shaq Center” and has the Miami Heat logo. The 95-foot-long swimming pool with a waterfall extends into an outdoor dock. Other perks include a cigar room, a home theater, and a 17-car garage.

Not to be humbled, Shaq’s G.O.A.T. has nine bedrooms, 19 bathrooms, five fireplaces, a massive den, and more in his home. A full regulation-size indoor court, a cigar room, an infinity pool, and greenery are its famous features.

O’Neal had several personalizations, including his love for Superman, showcased in his house. But it underwent several renovations, and the new owners reportedly removed the Big Diesel elements. However, de-Jordan-ifying the Chicago mansion, like its #23 gates, would be a lot more expensive for the next owner, which has deterred buyers before.