the biggest bets, trades and fortunes, told from the first move. real people, sourced stories.
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Paul Heyman put most of what his family had into a wrestling company that taped its TV in a Philadelphia bingo hall. 7 and a half years later he was filing for personal bankruptcy.
When he took over ECW, the owner was already $470K deep into a $500K line of credit. In his words, they were on death's door.
The interviewer says it was $4 million from his parents. Heyman says he honestly doesn't know how much he spent. He never paid himself, whatever he had just went into keeping the company alive.
He was up against Ted Turner's WCW and Vince McMahon, both billion dollar companies on national cable.
"And here I am at a bingo hall in Philadelphia with a local sports channel clearance."
Then came the day he had to accept it was going into bankruptcy. He calls even that day a great day.
The interviewer didn't buy it either. In the video below he explains exactly why he meant it.
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Kelly Slater went on to win 11 surfing world titles. Around 21, with one title already won and over $1 million made, he found out he was in debt.
He was trying to buy a house with his then fiancée. That's how it came out.
He grew up with no money. His mom raised 3 boys on about $2,000 a month without much help from his dad, and most days she was scraping quarters together to pay for his school lunch.
"It's not a sob story. It's just the way it was in my family."
He says when you're raised like that you don't have a lot of intelligence around money. So once he was getting paid he didn't handle his finances at all, his mom just took care of it for him.
"It was a real kind of quick wake-up lesson."
I kind of get it. If nobody ever showed you, you don't go looking at the numbers until something like a house makes you.
In the video below he says the first thing he changed after that.
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Charlie Sheen was paid $1.8 million an episode on Two and a Half Men. Today he wears a Timex and drives a Cadillac.
He says he did money in reverse. Most people start in apartments and townhouses, strike gold, then move into mansions. He had the mansions early. Now it's totally flipped.
"It's kind of refreshing."
He once owned one of the nicest vintage watch collections in the country. He was still late to everything. Sometimes not by hours. By days.
"How many cars can you drive at the same time? How many watches can you wear?"
Then he talks about a drive with his buddy Eddie Braun, his old stunt double. Years earlier Sheen had handed Eddie a $1 million check to stop doing stunts.
In the car Sheen said he gave it all away. Burned it all to the ground.
"Now what?"
In the video below he repeats exactly what Eddie told him.
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Jason Tatum signed a $314 million deal with the Celtics. The morning after a trip with his friends, his mom still calls him.
"Who is Mr. Jones? Why did you give him $12,000?"
He only takes those trips once or twice a year. LA, Vegas, Miami. Everything that has to do with Jason Tatum goes through her, so she processes every wire and gets every receipt.
She says she can tell from his face when he walks into her office that a wire is coming. He's already picked something out. He likes nice watches.
"What does this watch do?"
Before he got drafted, they made a deal. He couldn't spend the money he made from the Celtics. He had to live off endorsements. His mom and his accountant both agreed.
They didn't know he'd make as much off the court as he did.
In the video below he explains the loophole he found in that deal.
Joe Gibbs had already won three Super Bowls. Six months into his NASCAR team, he found out they were $250,000 in the hole.
He heard it at dinner, right as he was about to take a bite of his swordfish.
"This is absolute panic."
The team started with nothing. His son JD told him he'd rather do racing than football. Gibbs said they didn't have anything, but they could put a dream on a piece of paper and try to sell it.
He showed up at Interstate Batteries. First question: who's your driver?
"We don't have one."
Where's your race shop?
"We don't have one."
Two days later the answer was yes. Year one was 17 people, one car and zero wins. They cut back, watched every dollar and stopped going deeper into debt.
Year two, first race of the season, the Daytona 500. They were running up front, and it came down to the last pit stop. JD was changing the tires.
In the video below he repeats exactly what JD said when they asked if he got the lug nuts tight.
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Greg Norman was getting paid millions to wear other companies' logos. He decided that was the problem.
He was one of the few athletes in the world getting that kind of endorsement money. He was repped by IMG, the famous sports management firm.
They paid him. He wore their logo. Every time he played well, their brand got minutes of TV time.
"I really didn't get anything out of it except dollars."
Most athletes would stop there.
"I didn't want that. I wanted to build equity in my own brand."
One problem. He didn't have a brand.
Then the man who owned Reebok told him something about the Shark logo. When his management contract came up in 1993, Norman didn't renew and paid for everything himself.
In the video below he says exactly what he heard, and what happened once the cash started going out.
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Barry Diller took Home Shopping Network from losing $70 million a year to making $60 million. Within a year.
Asked how, he gave a one-word answer.
"Easy."
The company wasn't broken, he said. It was mismanaged. Then the internet showed up, and he already knew how people bought things through a screen.
"That created 100 billion dollars of value."
Then 9/11 hit. Travel stopped worldwide, and Expedia, the travel company he was buying, had no revenue at all.
"It was like dead cold."
What one person in the room said next, and what Diller decided to bet on, is in the video below.
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Tony Romo was an undrafted backup making the league minimum when Jerry Jones and Bill Parcells offered him $500,000. He asked for $2 million.
It was his second year in the NFL. They sat him down right before a preseason game.
His logic was simple. If they had real money in him, they would have to put him in a game and see if he was worth it.
"Believe me, I didn't want to do it."
Jerry said yes on the spot.
What Parcells told Jerry the second Romo walked out of that room is in the video below.
"Oh my gosh, I'm the richest guy in the world."
Shaq once turned down Howard Schultz and his own Starbucks stores with one sentence.
Schultz wanted him to open Starbucks locations in Black neighborhoods.
Shaq grew up on sweet tea and hot chocolate. He had never seen anyone in his family drink coffee.
So he looked Schultz in the face and told him it wouldn't work.
In the video below he explains exactly what he said, and who took the deal right after him.
"On every corner, in every city, in every country, I see a Starbucks."
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Donald Trump once mailed John McEnroe a letter offering $1 million to play Serena or Venus Williams. McEnroe said no.
He was calling a match when the envelope showed up.
"Dear John, I want to offer you $1 million to play either Serena or Venus."
Serena and Venus had been saying they could beat a lot of guys. Somehow McEnroe became the one everybody asked.
He was the number one player in the world. He wasn't going to sit there and say he couldn't beat them.
So why turn down $1 million?
In the video below he explains exactly why. Then he asks a question about the NBA that nobody else gets asked.
"Somehow it's me, the old fart."
Vince Young signed an NFL deal worth up to $58 million. Less than 8 years later he filed for bankruptcy, and a lender was coming for his Rose Bowl rings.
$25.7 million of that rookie deal was guaranteed.
The lender said he took out a high-interest $1.9 million loan. Vince says the money never hit any of his accounts.
They got a judgment against him anyway. Rose Bowl rings, trophies, cars, the house, all on the table.
"You never took a dime from the person... but you suing me. It was painful."
Filing for bankruptcy was embarrassing, he says, mostly because of "me being who I am."
His uncle was part of the team around him back then. "It's my dad's brother, so I definitely thought that he had my back a little bit more."
Asked if he'd do anything differently with the money, he says no. If his mom needs $1,000, she gets $1,000, and he goes to work to put it back in the account.
What he learned:
"Definitely don't sign a power of attorney."
"Sign your own checks."
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Bob Costas got his father's entire estate in an envelope at the wake: $6,000 in $100 bills, collected from a bookie.
His dad didn't bet at casinos or the track. He bet on ballgames.
The mortgage literally rode on the outcome.
Bob liked watching the games with him. When the Christmas money was going down the drain and his mom and sister fled, he stayed.
"At his best, if he was flush with cash, he was very, very generous."
May 15, 1970. Bob is 18. A cop knocks, looks past him and tells his mother to sit down. Heart attack, walking through JFK Airport.
Sunday at the wake, a gambling buddy named Steve Collins hands Bob a thick envelope.
"Your father was up when he died. Give this to your mother."
A bookie will never pay a dead man. So Steve went to the bookie and said "John sent me to collect."
$6,000. All in $100 bills.
"That was my father's entire estate."
Bob went on to call the Olympics for NBC. His father never saw or heard any of it.
"I'll never know."
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Terrell Owens made north of $50 million in the NFL. Then he saw the true state of his finances.
8 years in San Francisco. Then a new contract with the Eagles.
It was around 2004, 2005. He was switching agents.
"I did not have the financial security that I thought I had."
How big was the gap between what he thought he had and what he really had?
"I think it was a considerable difference."
He puts it on himself first: "Not being smart enough, responsible enough to be on top of my financial situation."
He also trusted the people around him. They looked his brothers and sisters in the eyes, and he felt they had his best interests at heart.
A lot of people say he's broke.
"I have money. If you want to look at me and say I'm broke and famous, that's cool."
"I wouldn't say I'm broke. Maybe in a financial bind."
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Henry Winkler's father took his bar mitzvah money and never paid it back. Henry now jokes his kids will inherit $350.
He was 13. The family lived above its means. His father kept a summer home an hour outside New York City.
Henry put the cash and the bonds in the bank.
Then his father came to him. "I need your bar mitzvah money."
"Will you pay me back?"
His father said he didn't have to. "After everything I've given you."
"It was my gift for my 13th birthday."
Decades of success later, the Fonz still calls money "the bane of my existence."
"Money makes me crazy. You always think you're going to run out."
"There is no connective tissue between the reality and what I live in my head."
His kids were told there will be no inheritance. Henry says he has no idea where that came from.
"I believe that there will be at least $350 left. And then you guys can just divide that amongst yourselves."
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Matthew McConaughey was offered $14.5 million for one rom-com. He said no.
He was the go-to rom-com guy. Easy movies, fun movies, good money, high demand.
The catch: nobody would even consider him for a serious role.
"If I can't do what I want to do, I'm going to stop doing what I've been doing."
So he called his agent. No more rom-coms.
The first 6 months, nothing came in but rom-coms. Some big offers.
One came in at $14.5 million.
"I said no."
Then nothing. No offers at all. Nobody mentioned his name for another 14, 15 months.
There were moments he thought he'd have to find another career.
"I didn't want out. I just wanted in in a different way."
About 20 months in, the calls came back. The Lincoln Lawyer. Killer Joe. Magic Mike. True Detective. Dallas Buyers Club.
Dallas Buyers Club won him the Oscar.
The $14.5 million he turned down was the price of the ticket.
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