Steve Harvey says he owed the IRS $22 million for taxes he thought he’d already paid.
In 2008, after his accountant died, an employee found seven years of Harvey’s signed tax forms and checks still sitting in the office. Harvey says money had been leaving his account, so he believed the payments were going through. His lawyer told him the returns had never been filed.
With penalties, the bill reached $22 million.
Harvey recalls accidentally joining a conference call about the debt and hearing someone ask what they would do when he went to jail. He hung up, went upstairs and told his wife, Marjorie. She cried for two days.
When she asked what he would do, he told her: “I’m going to go to work.”
He says he took every comedy gig he could, worked every Friday, Saturday and Sunday, and sent $650,000 a month to the government for four years while keeping up with his current taxes.
In 2012, he says he sold 49% of his radio company. He used the check to clear the remaining debt.
“And that was the first time, man, I could breathe.”
Shaquille O’Neal signed a $1 million endorsement deal before entering the NBA.
He says he spent the money in one day.
A few days later, his bank called: his account was $80,000 overdrawn.
Shaq had treated the million as money he could spend. In the interview, he explains that after taxes, he actually had roughly $600,000.
His first purchase was a $150,000 black Mercedes. He paid the asking price without negotiating.
Then he drove home.
His father took one look: “That’s nice. Where’s mine?”
Shaq took him back to the dealership and bought another.
His mother wanted a smaller one. He bought that too.
Then came suits for the draft, jewelry, earrings, and a car stereo. He knew more money was coming, so he kept buying.
The bank manager, a family friend, sat him down with his statement. Shaq remembers feeling embarrassed.
The manager told him:
“I don’t want you to be like all these other athletes.”
Shaq decided he needed a financial adviser.
Some candidates promised they could turn his expected $40 million contract into $200 million by age 23. He didn’t trust them.
One talked about savings bonds and setting up the family’s finances.
Shaq hired him.
Even then, the spending didn’t disappear. Later, after buying two Rolls-Royces for $600,000, Shaq got another call.
This time, his adviser was telling him to stop.
Mike Tyson earned an estimated $400 million during his boxing career. In 2003, he filed for bankruptcy.
Years later, he explained what spending all that money had actually felt like.
In a 2011 interview, Graham Bensinger reads back a list of Tyson’s expenses: luxury cars, gifts, jewelry, and a house with 38 bathrooms.
Tyson sounds almost disconnected from the person being described. Looking back, he struggles to imagine living that way again.
He connects the spending to growing up poor, anger, and an addictive personality. The same intensity that helped him in boxing could turn toward destroying himself.
When Bensinger asks about the support system around him, Tyson says he never had a good one. Then he takes responsibility:
“I blame everything on myself.”
Later, Bensinger asks how satisfying it was to have that much money.
Tyson compares it to drugs. He describes spending more and more, trying to fill an emptiness that never went away.
By the time of the interview, he says he has far less, but can do more with it. His priorities have changed: his health, his children, taking care of his family.
His final answer:
“I don’t know what I want. I know I don’t want what I already had.”