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CEO Rap Sheet

Over $191.7B in fines have been levied against corporate executives for fraud, insider trading, and regulatory violations. This tracker covers 30 executives with outcomes ranging from conviction to acquittal.

30 executives tracked — ranked by shame score

30
CEOs Tracked
$191.7B
Total Fines
18
Convicted
5
Never Charged
5
Still Active
10 /10
Jeffrey Skilling
Enron ENE · 2001

Orchestrated one of the largest corporate frauds in history. Enron's fake accounting hid billions in debt. 20,000 employees lost jobs and pensions. Skilling sentenced to 24 years.

🎭 FRAUD ⚖️ CONVICTED Fine: $45M
10 /10
Bernie Ebbers
WorldCom WCOM · 2002

Directed an $11B accounting fraud at WorldCom, the largest in history at the time. Sentenced to 25 years. Died in prison in 2020 after compassionate release.

🎭 FRAUD ⚖️ CONVICTED
10 /10
Sam Bankman-Fried
FTX · 2022

Stole $10B+ in customer deposits from FTX crypto exchange to fund Alameda Research. Convicted on 7 fraud and conspiracy counts. Sentenced to 25 years. The crypto Bernie Madoff.

🪙 CRYPTO ⚖️ CONVICTED Fine: $11.0B
10 /10
Do Kwon
Terraform Labs · 2022

Designed the Luna/UST stablecoin that collapsed in May 2022, wiping out $40B and destroying life savings. Fled to Montenegro, was arrested, extradited. SEC won a $4.5B judgment.

🪙 CRYPTO ⚖️ CONVICTED Fine: $4.5B
10 /10
Ken Lay
Enron ENE · 2001

Enron founder who built the fraud factory. Encouraged employees to buy stock while secretly selling his own. Convicted on 10 counts. Died of a heart attack before sentencing, vacating the conviction.

🎭 FRAUD ⚖️ CONVICTED
10 /10
Bernie Madoff
BMIS · 2008

Ran the largest Ponzi scheme in history for at least 17 years. $64.8B in stated client assets vanished. Thousands of victims including charities. Sentenced to 150 years. Died in prison.

🎭 FRAUD ⚖️ CONVICTED Fine: $170.0B
9 /10
Elizabeth Holmes
Theranos · 2018

Claimed Theranos could run hundreds of blood tests from a single drop. It couldn't. Defrauded investors of $700M+ and endangered patients with fake test results. Sentenced to 11 years.

🎭 FRAUD ⚖️ CONVICTED
9 /10
Richard Fuld
Lehman Brothers LEH · 2008

CEO during Lehman's $691B collapse that triggered the global financial crisis. Used Repo 105 accounting tricks to hide $50B in debt. Never criminally charged despite congressional grilling.

🎭 FRAUD 🤷 NO CHARGES
9 /10
Angelo Mozilo
Countrywide Financial CFC · 2008

CEO of the largest subprime mortgage lender. Made $140M selling stock while knowing loans were toxic. Settled with SEC for $67.5M. Never criminally charged. Ground zero of the housing crisis.

📄 SEC VIOLATION 💰 SETTLED Fine: $68M
9 /10
Martin Shkreli
Turing Pharmaceuticals · 2015

Raised the price of Daraprim (a life-saving AIDS drug) by 5,000% overnight from $13.50 to $750. Later convicted of securities fraud at his hedge fund. Sentenced to 7 years. Dubbed 'Pharma Bro.'

🎭 FRAUD ⚖️ CONVICTED Fine: $65M
9 /10
Markus Braun
Wirecard WDI · 2020

CEO of German fintech whose $2.1B in reported cash 'didn't exist.' Europe's Enron. Braun arrested, COO Jan Marsalek fled and is still missing. Company collapsed overnight.

🎭 FRAUD ⚖️ CONVICTED
9 /10
Andrew Fastow
Enron ENE · 2001

Enron's CFO who created the off-balance-sheet entities that hid billions in debt. Made $45M from the schemes. Cooperated with prosecutors, sentenced to 6 years. The architect of the fraud.

🎭 FRAUD ⚖️ CONVICTED Fine: $24M
9 /10
Allen Stanford
Stanford Financial · 2009

Ran a $7B Ponzi scheme through fake certificates of deposit in Antigua. FBI raided his offices. Convicted on 13 felony counts. Sentenced to 110 years in federal prison.

🎭 FRAUD ⚖️ CONVICTED
8 /10
Dennis Kozlowski
Tyco International TYC · 2002

Looted $600M from Tyco. Infamous $6,000 shower curtain and $2M birthday party on the company dime. Sentenced to 8-25 years. Released in 2014.

🎭 FRAUD ⚖️ CONVICTED Fine: $70M
8 /10
John Stumpf
Wells Fargo WFC · 2016

Oversaw creation of 16 million fake customer accounts to hit sales targets. Employees opened accounts without permission, charged fees on them. Fined $17.5M personally, clawed back $41M. Banned from banking.

🎭 FRAUD 💰 SETTLED Fine: $18M
8 /10
Michael Milken
Drexel Burnham Lambert · 1989

The 'Junk Bond King' who revolutionized high-yield debt. Indicted on 98 counts of racketeering and fraud. Pled guilty to 6 felonies, paid $600M in fines. Banned from securities. Later pardoned by Trump.

💸 INSIDER TRADING ⚖️ CONVICTED Fine: $600M
8 /10
Ivan Boesky
Boesky Corp · 1986

The original Wall Street insider trader. His cooperation brought down Michael Milken and Drexel. Fined $100M, sentenced to 3.5 years. Inspired Gordon Gekko's 'Greed is good' speech.

💸 INSIDER TRADING ⚖️ CONVICTED Fine: $100M
8 /10
Raj Rajaratnam
Galleon Group · 2011

Ran the largest hedge fund insider trading ring in history. FBI wiretaps caught him receiving tips from Goldman Sachs board members. Sentenced to 11 years. Forfeited $53.8M.

💸 INSIDER TRADING ⚖️ CONVICTED Fine: $54M
8 /10
Trevor Milton
Nikola NKLA · 2020

Claimed Nikola had a working hydrogen semi-truck. The demo video was a truck rolling downhill with no engine. Convicted of 3 fraud counts for lying to investors. Sentenced to 4 years.

🎭 FRAUD ⚖️ CONVICTED
7 /10
Adam Neumann STILL ACTIVE
WeWork WE · 2019

Burned through $16B trying to IPO a real estate company as a tech startup. Self-dealing: charged WeWork $5.9M for his own 'We' trademark. Ousted before IPO. Got $1.7B exit package.

🎭 FRAUD 🤷 NO CHARGES
7 /10
Changpeng Zhao (CZ)
Binance · 2023

CEO of the world's largest crypto exchange. Pled guilty to AML violations for allowing money laundering and sanctions evasion. Binance fined $4.3B. CZ sentenced to 4 months in prison.

🪙 CRYPTO ⚖️ CONVICTED Fine: $50M
7 /10
Lloyd Blankfein
Goldman Sachs GS · 2010

Goldman sold toxic mortgage CDOs to clients while secretly betting against them. Famous 'Fabulous Fab' emails. Testified to Congress that Goldman was 'doing God's work.' $550M SEC settlement.

📄 SEC VIOLATION 💰 SETTLED
7 /10
Carlos Ghosn
Nissan / Renault NSANY · 2018

Auto industry titan arrested in Tokyo for hiding $80M+ in compensation. Escaped Japan while out on bail by hiding in a musical equipment box on a private jet. Now a fugitive in Lebanon.

🎭 FRAUD 🏃 FLED
7 /10
John McAfee
McAfee / Various · 2020

Antivirus pioneer turned crypto pump-and-dumper. Charged with tax evasion and crypto fraud. Made millions promoting ICOs without disclosing payments. Found dead in Spanish prison cell before extradition.

🪙 CRYPTO ⚖️ CONVICTED
6 /10
Travis Kalanick
Uber UBER · 2017

Fostered a toxic culture including harassment, discrimination, and surveillance of competitors. Uber used 'Greyball' tool to evade regulators. Forced to resign as CEO. Still a billionaire.

🚨 WORKPLACE 🤷 NO CHARGES
6 /10
Steve Cohen STILL ACTIVE
SAC Capital · 2013

SAC Capital pled guilty to insider trading, paid $1.8B. Cohen personally was never charged despite 8 employees being convicted. Banned from managing outside money for 2 years. Now runs Point72.

💸 INSIDER TRADING 🤷 NO CHARGES
6 /10
Jamie Dimon STILL ACTIVE
JPMorgan Chase JPM · 2020

Under his leadership, JPM accumulated $34.2B in fines — the most of any bank CEO in history. Includes mortgage fraud, precious metals manipulation, and the London Whale disaster. Still CEO.

📄 SEC VIOLATION 🤷 NO CHARGES
6 /10
Mark Zuckerberg STILL ACTIVE
Meta (Facebook) META · 2019

Cambridge Analytica scandal: 87M users' data harvested without consent. FTC fined Facebook $5B — largest FTC fine in history. Accused of knowing and ignoring the data misuse for years.

📄 SEC VIOLATION 💰 SETTLED Fine: $5.0B
5 /10
Elon Musk STILL ACTIVE
Tesla TSLA · 2018

Tweeted 'Am considering taking Tesla private at $420. Funding secured.' The funding was not secured. SEC sued, settled for $20M fine each (Musk + Tesla), forced to step down as chairman.

📄 SEC VIOLATION 💰 SETTLED Fine: $20M
4 /10
Jack Dorsey
Block (Square) SQ · 2023

DOJ and SEC investigations into Cash App for inadequate anti-money laundering controls. Block settled with multiple regulators. Cash App reportedly processed transactions for terrorists and sanctioned entities.

📄 SEC VIOLATION 💰 SETTLED Fine: $80M

Information compiled from public court records, SEC filings, and reporting.

Shame scores are editorial assessments based on impact, accountability, and public trust violations.

Not legal advice. Individuals are innocent until proven guilty.

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