The Most Expensive Things Billionaires Ever Lost

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An Old Fashioned, some red lipstick and a black dress…sigh, there’s just something undeniable about a good ol’ classic. The beloved Vegas showgirl may be an endangered species these days (insert tear), but “VEGAS! THE SHOW” preserved those feather-clad beauties and the likes of an era when everything was flashier and dripping with sophistication. What’s that you ask? Can a show filled with gorgeous and talented women a la Rat Pack era really exist in the here and now? Oh yes my friend, it sure can and all we have to say is raise that curtain and let the good times roll. With a little song, a lot of dance and that certain sultry allure that only old timey Vegas could pull off, this is a trip down memory lane and, well, it’s pretty legit. The costumes are fun, funky, sexy and so real. Ok, well maybe not the candy-themed costumes but hell, their Sammy Davis Jr. sure had us pining for an autograph. For a city that was built on pure, raw talent and obviously dolla dolla bills, this show celebrates iconic moments from the city's rich entertainment history through the decades that made the Vegas we know and love today. And we’ll tip our top hats to that.
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A yacht that sank four days old. A man with two password guesses between him and $537 million. A judge driving the car he seized. This is the most expensive stuff billionaires ever lost, from cheapest to the one that cost about $115 billion.

00:00 The $9 million yacht
01:01 Steve Wynn's Picasso
01:50 Two password guesses left
03:03 The hard drive in the dump
04:43 The $100 house
05:40 Sam Bankman-Fried
06:18 Bill Hwang
07:21 Jensen Huang's worst day
08:25 Eike Batista
09:08 The judge and the Porsche
09:44 The divorce
10:06 Gautam Adani
10:26 Meta
10:46 Number one
11:41 The final board

Sources:
Angiola II yacht (SuperYacht News; delivery photo: Superyacht Times): https://www.youtube.com/watch?v=SxF_Lbu7J_Q
Steve Wynn's Picasso: https://www.npr.org/blogs/thetwo-way/2013/03/26/175412881/years-after-the-elbow-incident-steve-wynn-sells-picassos-le-r-ve-for-155-million
Stefan Thomas and the IronKey: https://unciphered.com/blog/project-everest-cracking-the-ironkey
James Howells and the landfill: https://en.wikipedia.org/wiki/Bitcoin_buried_in_Newport_landfill
Howells' appeal: https://decrypt.co/310043/wales-man-loses-appeal-to-dig-out-hard-drive-holding-676-million-in-bitcoin
Dick Fuld's $100 house sale: https://www.cnbc.com/2009/01/26/fuld-sold-florida-mansion-to-his-wife-for-10.html
Sam Bankman-Fried: https://www.bnnbloomberg.ca/bankman-fried-s-assets-plummet-from-16-billion-to-zero-in-days-1.1844991
Bill Hwang and Archegos: https://www.bloomberg.com/news/features/2021-04-08/how-bill-hwang-of-archegos-capital-lost-20-billion-in-two-days
Hwang's sentence: https://www.nbcnews.com/news/us-news/archegos-bill-hwang-sentenced-18-years-prison-massive-us-fraud-rcna181134
Eike Batista: https://qz.com/120442/how-to-lose-97-of-your-30-billion-fortune-in-less-than-two-years
The judge and the Porsche: https://stabroeknews.com/2015/02/25/news/regional/brazil-judge-batista-case-seen-driving-tycoons-seized-porsche
Meta Reality Labs: https://aa.com.tr/en/economy/meta-s-reality-labs-loses-462b-as-revenue-outlook-falls-short/4013219
Masayoshi Son after the dot-com crash: https://www.bloomberg.com/news/articles/2017-10-11/how-softbank-s-son-bounced-back-after-the-dot-com-crash
SoftBank and Nvidia: https://fortune.com/2025/11/11/softbank-nvidia-openai-masayoshi-son-sam-altman-investment/
WeWork: https://www.cnbc.com/2020/05/18/softbank-ceo-calls-wework-investment-foolish-valuation-falls-to-2point9-billion.html
Elon Musk's record loss: https://www.usatoday.com/story/money/2023/01/10/elon-musk-guinness-world-record-losing-most-money/11022084002/
Gautam Adani after Hindenburg (allegations Adani denies): Bloomberg Billionaires Index, Jan-Feb 2023
Bitcoin prices: CoinGecko, Oct 31 2026

Music: Mixkit (mixkit.co)

This is not financial advice.
Category
Steve Wynn
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