Scottie Pippen was the 122nd highest-paid player in the NBA in his last season with the Bulls. A year later he signed for five years and $67.2 million.
That one deal was worth more than three times his whole seven-year Bulls contract. Chicago signed him and traded him to Houston for Roy Rogers and a second-round pick.
In the video below, November 1997, Pippen tells reporters he is done with Chicago. "I'm not going to play there anymore. And that's that. I have that freedom and I have that right."
The money still didn't stay. His financial adviser, Robert Lunn, told him a used Gulfstream jet was a good buy at about $1.35 million. Soon after, it needed a $1 million engine overhaul. He also lost money on a $3.25 million real estate investment.
In 2004 Pippen won a judgment of nearly $12 million against Lunn. He settled for $1.5 million. Ten years later Lunn was convicted of bank fraud and sentenced to three years in prison.
Pippen said he left his money decisions to advisers he trusted for his entire NBA career.
Underpaid by the Bulls, then burned by the people handling his money.
Which cost Pippen more, the contract he signed or the adviser he trusted?
Michael Jordan made $33.1 million in his last season with the Bulls. Scottie Pippen, his partner for six titles, made $2.775 million.
Pippen says the two of them never once had dinner alone together.
In the video below, he is asked why everything with Jordan still feels so tense. "Michael is a very difficult person to deal with," he says.
Pippen grew up poor in Hamburg, Arkansas. In 1991 he signed a seven-year, $18 million deal because he wanted security. The owner warned him it was too long.
Then NBA salaries exploded. By 1998 he was the sixth-highest paid player on his own team.
In 2020, The Last Dance made Jordan the hero of those years. Pippen later wrote that Jordan was paid $10 million for it, while he and his teammates got nothing.
He stopped watching halfway through. His kids were turned off by it.
In May 2020, Jordan texted him that he heard Scottie was upset. They spoke briefly. Pippen calls that talk "good and final."
"Great teammate," he says. "We just never were a great friend."
The case for Jordan: he never set Pippen's salary. Pippen signed that contract himself, against advice. And Jordan's drive is a big part of why they have six rings.
So did Jordan owe Pippen more than six rings?
@kaienphase He gave back $80,000 of the more than $311,000 Ruderman paid him. Other players settled in the same range. A Ponzi scheme covered his poker winnings, and the victims got about a quarter of it back.
@gosh_sol_eth Pippen signed a seven-year, $18 million deal in 1991 because he wanted security. By 1997-98 he was the sixth-highest paid player on his own team and 122nd in the NBA. Jordan made 12 times more that season. Six rings, one bad contract.
Pilar Sanders told a court Deion was worth $250 million and asked for $24,000 a month. Her prenup gave her $1 million. Her own lawyer from 1999 said the $1 million was her idea.
In the video below, Fox 4 in Dallas reports what that lawyer told the court. Pilar insisted on a $1 million settlement and a $100,000 "signing bonus" when she signed. Deion approved both.
Twelve years and three children later, she wanted it thrown out. Her lawyers said the initials on the agreement were not in her handwriting and were in a different ink.
Texas does not make that easy. A Dallas divorce attorney on the same broadcast explains that the law presumes a prenup is valid, and the person attacking it has to prove otherwise.
In October 2012, Judge Ray Wheless ruled she signed it willingly and told her lawyers not to bring the claim back.
When she put his net worth at $250 million, Deion laughed out loud in the courtroom. He testified the NFL Network paid him about $1 million a year. His 2010 tax return showed nearly $2 million.
In December 2022, Colorado gave him five years and $29.5 million. The prenup had capped her at $1 million for twelve years of marriage.
Did Pilar sign a bad deal, or exactly the deal she asked for?
@lyna55rede Jackson took the advice. In 1985 he bought ATV, Beatles songs included, for $41.5 million. In 2016 Sony paid his estate $750 million for its half of the merged catalog. Paul gave the best business advice of his life to the wrong person.
@darvinxq $27,000 a month is $324,000 a year, almost four times the median US household income. He still ran out by the 15th. The money never ran out. The month did.
Hulk Hogan left about $5 million. In their divorce, his ex-wife Linda walked away with $7.44 million in cash alone.
That was a little over 70% of the $10.41 million the couple had in bank and investment accounts. She also got a $3 million property settlement and 40% of his companies. No alimony. The deal was confidential until 2011, when it turned up attached to a new motion in court.
In the video below, Inside Edition asks Linda if she should get a share of Hogan's Gawker money. "I ended up with an okay settlement," she says. "I wouldn't want to share any of that."
In 2016 a Florida jury awarded him $140 million over the sex tape Gawker posted. The lawsuit had been secretly paid for by billionaire Peter Thiel. Gawker went bankrupt. Less than eight months after the verdict, Hogan settled for $31 million plus 45% of whatever https://t.co/7tljHHrOdv sold for.
When he died in 2025, court papers put his estate at about $5 million, and $4 million of that was the right to use his name. His son Nick got all of it.
His ex-wife's cash from the divorce was bigger than everything he left behind.
Did Linda end up with Hogan's fortune, or did he spend it himself?
Hulk Hogan left about $5 million. In their divorce, his ex-wife Linda walked away with $7.44 million in cash alone.
That was a little over 70% of the $10.41 million the couple had in bank and investment accounts. She also got a $3 million property settlement and 40% of his companies. No alimony. The deal was confidential until 2011, when it turned up attached to a new motion in court.
In the video below, Inside Edition asks Linda if she should get a share of Hogan's Gawker money. "I ended up with an okay settlement," she says. "I wouldn't want to share any of that."
In 2016 a Florida jury awarded him $140 million over the sex tape Gawker posted. The lawsuit had been secretly paid for by billionaire Peter Thiel. Gawker went bankrupt. Less than eight months after the verdict, Hogan settled for $31 million plus 45% of whatever https://t.co/7tljHHrOdv sold for.
When he died in 2025, court papers put his estate at about $5 million, and $4 million of that was the right to use his name. His son Nick got all of it.
His ex-wife's cash from the divorce was bigger than everything he left behind.
Did Linda end up with Hogan's fortune, or did he spend it himself?
Hulk Hogan left about $5 million. His will names his daughter only to cut her out.
The July 28, 2023 amendment reads: "Under no circumstances shall Brooke E. Bollea or any descendants of Brooke E. Bollea be considered a beneficiary."
Court papers listed $200,000 in crypto, $799,000 in personal and intellectual property and a $4 million right of publicity. Sole beneficiary: his son Nick.
Brooke had asked to be taken out. She said she did not want to fight her mother or his third wife over money after he was gone. She still hoped he would ask why.
He signed it. He had skipped her 2022 wedding and told her husband he doesn't do weddings or funerals anymore.
The case for Hulk: she asked, he did exactly what she asked.
The case for Brooke: she wanted a phone call, not a signature.
In the video below she says how quickly she was erased.
Was he honoring her wish or punishing her for it?
@Noctaxbt Nine years after a $31 million settlement with Gawker, 80% of his estate on paper was the right to use his name. Hulk Hogan was worth more than Terry Bollea.
The man who used to bet with Phil Mickelson says Mickelson wagered about $1 billion and lost around $100 million.
Billy Walters is one of the most famous sports bettors in America. For five years he and Mickelson were betting partners, each putting up half the money. In 2017 Walters was convicted of insider trading and went to federal prison.
In the video below, Walters tells ESPN where his number comes from. His own records of every bet, plus records from two other people Mickelson bet through starting in 1995. "That would be in gross wagers," he says, "and it probably lost around 100 million."
His book says that from 2010 to 2014 Mickelson made 858 bets of $220,000 and 1,115 bets of $110,000.
Walters also says Mickelson called him before the 2012 Ryder Cup wanting to put $400,000 on the US team, and that he refused. Mickelson denies ever betting on the Ryder Cup. He has said he has a gambling addiction and has gotten help.
"If you make in excess of a billion dollars and you lost 100 million," Walters says, "that's his business."
Is losing $100 million out of $1 billion an addiction, or just a rich man's hobby?
Prosecutors said he got $940,500 for the movie rights. In 2011, the year almost $1 million came in for the memoir rights, he paid $21,000 toward restitution. Most of what victims got back came from property he gave up at sentencing. The story paid him. The victims got the leftovers.
@scientxbt $125,000 was about 2% of his first $6 million. In 1999, after Yahoo bought https://t.co/EPTEIRVIFR, he bought a Gulfstream V over the internet for $40 million, a Guinness record for the largest single e-commerce sale. First class at 30, his own jet only after the billion.
@Truntr_ Part of the 1964 deal was a lifetime salary of $40,000 a year, roughly ten times that in today's money. The new owners got the company for $2 million and the face on every bucket for a salary.
@VegasMikeyM@levifizg Nobody. And every one of those rooms still needs heating, cleaning and property tax.
A big house doesn't make you rich. It makes you pay every month to look rich.
@callumxbt The bank said $82.3 million. The IRS said $163.2 million. In 2022 they settled at $156.4 million, almost double the bank's number. No will meant the IRS got to start the argument.
In 1992, Michael Jordan ran up a $1.2 million golf debt to a businessman named Richard Esquinas. Jordan agreed to pay $300,000. He paid $200,000 and stopped.
He never stopped gambling at that level.
In the video below, Cedric the Entertainer describes a night in Las Vegas with Jordan and Charles Barkley.
Barkley was at the roulette table, stacking chips on every spin. Cedric was next to him with a thousand dollars.
Then Jordan walked over and grabbed a stack of Barkley's chips worth about $150,000. When Barkley asked how much he took, Jordan told him it didn't matter: "I got you."
Later they moved to a table where they were betting $300,000 a hand. Cedric tried to join with his $100 chips. They told him to wait for the next one.
Then Cedric played golf with Jordan. He put $1,000 on every hole and lost all 18. Jordan and Barkley play for $25,000 to $30,000 a hole.
"They doing billionaire sh*t," he says.
Would you have kept playing after the first hole, or walked away from Michael Jordan's game?
@kaienphase Jordan's golf debt was $1.2 million. Billy Walters, his former partner's word, puts Phil Mickelson at about $1 billion wagered and around $100 million lost. Next to that, $1.2 million is a rounding error.
@kaienphase Barkley says he lost a million about 25 times. John Daly went through his own tax records and found $55 to $57 million in losses from 1991 to 2007. He had guessed $20 million. The casino never needed them to lose big. It just needed them to stay.
Thousands of Wall Street analysts were paid millions to read the fine print. They didn't read a single page.
Then a guy sitting alone in a t-shirt and shorts opened public SEC Form 424B5 filings and walked away with $725 million.
In the clip below, Michael Burry breaks down the exact moment he realized the entire system was built on total negligence.
When Burry started digging into the actual mortgage prospectuses, he found literal trash loans bundled into AAA ratings quarter after quarter. Rating agencies like Moody's and S&P didn't even have the manpower to check them. Nobody cared.
When asked if the banking executives even read the toxic debt they were selling, Burry gave a cold reality check:
"I don't think they read them. No... this was a profit center."
They didn't miss the crash because they were incompetent. They missed it because willful blindness pays nine figures until the building catches fire.
The biggest edge in finance hasn't changed since 2007: retail trusts the rating, institutions chase the fees, and the guy who actually reads the raw source data takes all the money.
What's the biggest "AAA-rated" trash everyone is blindly buying right now just because the yields look good?
In 2008, a Las Vegas casino took Charles Barkley to court over $400,000 in unpaid gambling markers. A prosecutor said he could face a felony charge if he didn't pay.
He paid. "I owe them the money," he said.
In the video below, Barkley tells Shannon Sharpe what his gambling actually looked like. He played $25,000 a hand at blackjack and only took his winnings in cash. "I don't want no check. I don't want you to wire."
He says he won a million dollars in a night about 7 times. He lost a million about 25 times.
His friends finally sat him down. They told him his gambling wasn't out of control. "You just a f***ing idiot." He would be up $400,000 and refuse to leave, because in his head they weren't going home until he won a million.
"You can never break the casino," Barkley says. "They can break you."
The losses hit harder than the wins ever did. After losing a million, he says he was depressed for a week. Then the bill went to his business people, and they yelled at him until he threatened to fire them.
Barkley earned more than $80 million from the NBA and endorsements. Estimates of what he lost gambling run from $10 million to $30 million.
Would you have walked away up $400,000, or kept playing for the million?