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.
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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