High Roller Files

the biggest bets, trades and fortunes, told from the first move. real people, sourced stories.

[High Roller Files @highrollerfiles]

Ted Turner was worth $7-8 billion. After the AOL merger, he told CNN you can get by on "a billion or two" if you economize.

In 1996 he merged Turner Broadcasting, the home of CNN, into Time Warner for $7.5 billion in stock. He owned about 10% of the combined company.

"I thought that I was buying Time Warner, not selling to them."

Then came AOL. The 2000 merger diluted him from 10% to 3%, and the stock collapsed with the dot-com crash. In 2002 AOL Time Warner posted a $99 billion loss, the biggest annual loss in US corporate history.

Asked if it was the biggest regret of his life, he said Time Warner was a very good company "before AOL was put into it, then it was toxic."

Once his stake was diluted, management came after him. He lost his job at the company he built.

In 2012 he summed it up on CNN:

"I lost my job here. I lost my fortune, most of it. Had a billion or two left. You can get by on that if you economize."

[High Roller Files @highrollerfiles]

@FinRetv the tigers were the fun part, the people around him were the expensive part, he basically says it himself at 0:42

[High Roller Files @highrollerfiles]

Mike Tyson made around $300 million in the ring.

By 2003 he was bankrupt and about $23 million in debt.

Mansions, Bengal tigers, an entourage on payroll. Then it was gone.

Years later he was asked what happened. His answer is not what you'd expect:

"Aside from me having a lot of fun, I allowed people to be involved with my life that really wasn't honest people."

"And that was my fault. I should have paid more attention to my business."

No bitterness. He says when he was making $30-40 million a fight, he couldn't get anything done. "I was a megalomaniac back then."

Now he calls going broke "probably the best thing that ever happened to me."

Watch 0:42. That's the part nobody expects from Mike Tyson.

[High Roller Files @highrollerfiles]

@darkcrypto_off giving her a job was smart

[High Roller Files @highrollerfiles]

@Plioric89 that 7 second pause says everything

[High Roller Files @highrollerfiles]

@FinRetv 5 million for one cardboard pikachu

[High Roller Files @highrollerfiles]

@darkcrypto_off 7 years of checks cashed and nobody in that office said a word. finding out only after the guy died is a nightmare for anyone who just trusts their accountant

[High Roller Files @highrollerfiles]

@softarox the wild part is she re-recorded half the catalog first, made the originals worth less, and still paid to get them back. that's leverage most artists never get

[High Roller Files @highrollerfiles]

In 2022, Sam Bankman-Fried was worth $26 billion.

Three weeks after FTX collapsed, he joined the New York Times DealBook Summit and was asked about his money.

"I've had a bad month."

Then he said the quiet part:

"I don't have any hidden funds here. Everything I have, I'm disclosing. I think I have one working credit card left. I think it might be $100,000 or something like that."

"I'd put everything I had into FTX."

FTX was valued at $32 billion at its peak. It filed for bankruptcy in November 2022, and billions in customer money were missing.

A year later, a jury found him guilty on all 7 counts. He got 25 years.

From $26 billion to one credit card in under a month.

[High Roller Files @highrollerfiles]

@BookitWithTrent every game on opening night is the move, small stakes and just vibe with it

[High Roller Files @highrollerfiles]

@TrendSpider a former ceo dropping 23.7 million at the worst drawdown since 2008 is the kind of conviction you don't see often, he knows that business better than anyone

[High Roller Files @highrollerfiles]

@PatrickE_Vegas @primesportsbook eagles getting the sharp money at +4 is interesting

[High Roller Files @highrollerfiles]

@A6788C rough weeks happen when you bet volume, the fact you're still green on a few is what keeps the long run alive, good luck on the treble tonight

[High Roller Files @highrollerfiles]

@br_betting an int and a td on the same day at +164 is the kind of prop nobody bets until it hits lol

[High Roller Files @highrollerfiles]

@CrashiusClay69 10k on a completions prop is a serious first bullet, if marvin eats early this one cashes before halftime

[High Roller Files @highrollerfiles]

@Dexerto getting banned for match fixing and then posting stacks of cash is the fastest way to turn 3 years into forever lol

[High Roller Files @highrollerfiles]

@Cointelegraph whoever that fund is, their prime broker is having a way worse friday than cramer

[High Roller Files @highrollerfiles]

@CollinRugg founders series buyers parked $250k back in 2017 and waited 9 years for this moment lol

[High Roller Files @highrollerfiles]

@leevalueroach buying real stuff when inflation runs hot is the oldest play in the book ngl. the hard part is sitting through the first dip

[High Roller Files @highrollerfiles]

@TheStalwart hottest ppi in 4 years and the market opened like nothing happened, wild. feels like the calm part before someone gets margin called