Long before he became one of the richest athletes in the world, Shaquille O’Neal learned an expensive lesson in a hotel room in Orlando. In 1992, the LSU star was the No. 1 pick in the NBA Draft and soon signed a seven-year, $40 million deal with the Orlando Magic, the largest contract in professional sports at that time. Before he had played a single NBA game, though, he had already run up a bill of roughly half a million dollars at the Hyatt.

A couple of days before the draft, O’Neal had his parents flown to Orlando and checked them into the Hyatt. His brothers and sisters came along too. The family ended up living there for three months, and nobody kept an eye on the tab. Room service, movies and everything else went straight onto the room bill.

“I stayed at the Hyatt and spent like $500,000. It was me, my mother and father, brothers and sisters,” O’Neal shared in a statement published on Grantland. “Room service, movies. They go downstairs, charge it to the room. Three months later, half a million. My accountant says, ‘You know you could have bought a house by now?'”

The hotel bill wasn’t Shaq’s only early money mistake. Around the draft, he received his first big check, a $1 million endorsement deal, and spent it almost immediately. He bought a black Mercedes-Benz for about $150,000, paid the full sticker price for a second one so his father could have one too, and bought a smaller model for his mother. He also spent heavily on jewelry and a suit for draft night.

The problem was that he never had $1 million to begin with.

“I forgot about the agent fees, I forgot about FICA. I forgot about taxes,” O’Neal said on Oprah’s Master Class. He estimated he had netted about $700,000.

A few days later, his bank called. “I spent it in one day,” O’Neal told journalist Graham Bensinger. “I was $80,000 in the hole.” He added, “I was real embarrassed.”

However, within a few months, Shaq had endorsement deals with Reebok and Spalding on top of his record contract with the Magic.

The accountant’s comment about the house hit Shaq hard because a house was exactly what he wanted to buy with his first NBA money. Early in his Magic career, he did. O’Neal has said he went house-hunting with his mother, Lucille, in the gated Alaqua Lakes community north of Orlando and settled on a $700,000 home she didn’t think the family could afford.

“And I tell the lady, ‘I’ll take it; give you cash,’” O’Neal recalled. He then pulled out a briefcase, and the money was counted out in front of his mother, who broke into tears.

On top of purchasing their new home, O’Neal also paid off his parents’ remaining debts so they could live their retirement peacefully without ever having to worry about any other setbacks.