Allen Iverson earned about $200,000,000 in salary and endorsements. Reebok reportedly put $32,000,000 in a trust he can't touch until he turns 55. His wife divorced him, then took him back.
In the video below, Iverson explains how a kid who got 15 years for a fight became a millionaire with no blueprint, and what he finally gave up to keep his family.
At 17 he was locked up after a bowling alley brawl. "No guns, no knives, no chains, nothing." He asked his grandmother why God would do this to him. She told him never to question God. He says he never did again.
At 21 he was rich. "I never had nobody in my family that ever had money." Nobody to tell him what to do with it.
Then the drinking. He says he used to pray through hangovers: get me through this and I'll never drink again. Then he would drink again.
About six months before this interview he finally stopped. No AA, no therapy. His wife Tawanna told him it was the first time he actually kept that promise.
"Everything that ever happened with any type of separation had something to do with me." They have been together 35 years.
And Reebok? A lifetime contract, because they stayed loyal to him.
Did Allen Iverson blow his fortune, or did the people who stayed save him?
Dan Bilzerian says his trust fund started at $100,000,000. He says he had to sign over a third of it to get his father out of prison. By the time he sold the rest, it was worth a million or two, while he was making $50,000,000 a year playing poker.
In the video below, he explains where the Instagram money really came from.
Everybody says he is just a rich kid spending his dad's money. He says he never argued with it. He leveraged it. That story got him into the biggest private games.
His happiest win? He owned 25% of another player who won $42,000,000 in one night. He woke up to a text: you get $10,500,000.
Then he tells the real trick. In 2011 he split a $20,000,000 cliffside mansion and paid $1,500 a month. He filled it with furniture and cool cars. He looked like he had hundreds of millions. He says he had maybe $3,000,000 in the bank.
The poker games paid for everything. The girls working the tables made him money too, because he took half their tips. That got him into games with billionaires. He says he beat one guy for $42,000,000 in his own house.
His father was convicted of securities fraud in 1989. In 2024 federal prosecutors charged him again, and Dan's company Ignite was charged in the same case.
And Ignite? Dan says the board kicked him out as CEO, and a $750,000,000 sale fell apart.
Was it ever really his money?
Boris Becker won Wimbledon at 17. In 2022 a London court gave him two and a half years for hiding assets in his bankruptcy. Inside, another prisoner looked him in the eye and said: "I'm going to kill you. I'm going to slice your throat."
In the video below, he talks about the 231 days he spent behind bars.
He had found a stranger in his neighbour's cell and asked what he was doing there. The man started screaming in his face. Becker was very scared. The only thing between them was his food tray.
Then the other men on his floor came out of their cells. Go back inside, we'll take care of it. Prison rules. The man would pay a price.
How much money did he have left? "Zero. I lost everything." He says he lost his house in Mallorca, his flat in London and his house in Germany. About 15 million, gone.
On day one they take your photo and hang a badge around your neck. You are no longer Boris Becker. You are a number.
He got a single cell because he was "at risk". His other fear was the showers. They lock from the inside, and the guards don't go in.
The hatch on his door was broken, so he heard every scream at night.
The biggest shock? How dangerous it is. People get killed in prison and nobody ever hears about it.
Would fame protect you in there, or make you a target?
Hunter Biden says he was smoking crack every 15 minutes while his business, his marriage and his taxes all fell apart. One night they found him floating face down in a hotel hot tub.
In the video below, the president's son tells the whole story himself.
Someone at a drug dealer's hotel party had given him something. He woke up 12 hours later. One stranger had pulled him out and held him the whole time. Everyone else stole the shoes off his feet and took his clothes.
It started when his brother died. The only nightmare he ever had as a kid was losing him. Then his wife of 20 years stopped talking to him, and he fell apart.
A year later he admitted to one drink at his outpatient program. They insisted on a test. He walked out to a park not far from the White House, saw a woman he knew from the street and asked her: "Do you got any crack?" The run lasted almost 3 years.
Motels off the highway. Rooms by the hour. People who latched on and drained everything, down to his bank account.
In 2018 he bought a handgun on a whim while waiting for his phone to be fixed. It sat in a lockbox for 10 days. It became a federal case.
The big laptop reveal, he says, was that he was a crack addict.
His father, he says, has not gone a single day of his life without calling or texting him. He has been sober since June 2019. In December 2024, that same father pardoned him.
Would you have pardoned your own son?