The worst things companies have done for money are the ones with the clearest paper trails: guilty pleas, fines, bankruptcies and settlements, from Enron in 2001 to Purdue Pharma’s April 2026 sentencing. We rebuilt this list around documented, resolved cases with real outcomes and dropped older entries that rested on claims we could not confirm.
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The 15 cases at a glance
| # | Company or case | Year | What happened |
|---|---|---|---|
| 1 | Volkswagen | 2015 | Software that detected emissions tests |
| 2 | Facebook and Cambridge Analytica | 2018 to 2019 | Data of up to 87 million users harvested |
| 3 | Wells Fargo | 2016 to 2018 | Accounts opened in customers’ names |
| 4 | Purdue Pharma | 2007 to 2026 | OxyContin marketing |
| 5 | Enron | 2001 | Fraud and the largest bankruptcy of its day |
| 6 | Boeing and the 737 MAX | 2019 to 2024 | Safety information withheld from regulators |
| 7 | Bell Pottinger | 2016 to 2017 | A PR campaign built on racial tension |
| 8 | Danske Bank | 2007 to 2022 | Money laundering through the Estonian branch |
| 9 | Equifax | 2017 | 147.9 million Americans exposed |
| 10 | BP and Deepwater Horizon | 2010 | A rig explosion and 87 days of oil flow |
| 11 | Theranos | 2003 to 2022 | Blood-testing claims that were not true |
| 12 | Wirecard | 2020 | 1.9 billion euros missing |
| 13 | Mylan and the EpiPen | 2009 to 2016 | Price increases on a life-saving device |
| 14 | Coca-Cola in Plachimada | 2000 to 2017 | Dry wells next to a bottling plant |
| 15 | Deforestation for cheap commodities | Ongoing | Forests cleared for palm oil, cattle, soy and more |
The cases are not ranked by blame. Figures are the amounts reported at the time or in the settlement.
1. Volkswagen: Software that detected emissions tests
Volkswagen installed software in diesel cars that could detect when a laboratory emissions test was running, so the cars looked cleaner than they were on the road. The company agreed in June 2016 to pay up to $14.7 billion to settle civil charges in the United States, pleaded guilty to criminal charges in January 2017, and by June 2020 the scandal had cost it about $33.3 billion in fines, penalties, settlements and buybacks. In May 2025, four executives were sentenced in Germany. The scandal is a reminder that cheating a test is cheaper than building a better engine, until it is not.
2. Facebook and Cambridge Analytica: Data of up to 87 million users harvested
An app called This Is Your Digital Life collected the personal data of users and their friends, and the data of up to 87 million Facebook users ended up with Cambridge Analytica. In July 2019 the U.S. Federal Trade Commission approved a record $5 billion fine against Facebook for violating earlier privacy orders. Public awareness rose; user habits mostly did not.
3. Wells Fargo: Accounts opened in customers’ names
Employees opened unauthorized accounts in customers’ names to hit sales targets. The bank agreed to a $142 million settlement with affected consumers in March 2017, and by December 2018 it had paid $2.3 billion in settlements and consent orders, which a further $575 million state settlement lifted to nearly $3 billion.
4. Purdue Pharma: OxyContin marketing
Purdue pleaded guilty in 2007 to misleading the public about OxyContin’s risk of addiction, paying $600 million. It filed for bankruptcy in September 2019 and pleaded guilty to three federal felony charges in November 2020. On 28 April 2026 a federal judge sentenced the company to a settlement valued at about $8 billion, including a $3.5 billion criminal fine and a $2 billion forfeiture, and ordered it to dissolve and be replaced by a new corporation focused on public benefit.
5. Enron: Fraud and the largest bankruptcy of its day
Enron filed for bankruptcy on 2 December 2001 with $63.4 billion in assets, then the largest corporate bankruptcy in U.S. history. Its stock had fallen from a high of $90.75 in August 2000 to under $1 by the end of November 2001. Its auditor, Arthur Andersen, was dissolved, and shareholders were eventually compensated $7.2 billion out of a $40 billion suit.
6. Boeing and the 737 MAX: Safety information withheld from regulators
Two 737 MAX crashes in less than five months killed 346 people, and the plane was grounded worldwide from March 2019 to December 2020. Boeing agreed in January 2021 to pay over $2.5 billion after being charged with fraud over hiding information from safety regulators: a $243.6 million criminal penalty, $1.77 billion in damages to airline customers and a $500 million fund for crash victims’ beneficiaries. In January 2024 a door plug blowout on an Alaska Airlines 737 MAX 9 led to another grounding of some 171 jets.
7. Bell Pottinger: A PR campaign built on racial tension
The British PR firm ran a campaign for Oakbay Investments, controlled by the Gupta family in South Africa, that played on racial animosity and used fake news. It came to light in 2016 and 2017, and the firm went into administration on 12 September 2017. It is a rare case where the scandal ended the company.
8. Danske Bank: Money laundering through the Estonian branch
About 800 billion euros of suspicious transactions flowed through Danske Bank’s Estonian branch between 2007 and 2015. The bank pleaded guilty in 2022 and agreed to a settlement of around $2 billion, and in February 2019 it announced it would stop banking in the Baltic countries and Russia.
9. Equifax: 147.9 million Americans exposed
A breach between May and July 2017 exposed the records of 147.9 million Americans, plus millions of British and some Canadian consumers. Equifax settled with the FTC, the CFPB and states in July 2019, including a $300 million fund for victim compensation and $175 million to the states.
10. BP and Deepwater Horizon: A rig explosion and 87 days of oil flow
The Deepwater Horizon explosion on 20 April 2010 began the largest marine oil spill in the petroleum industry’s history. Oil flowed for 87 days and an estimated 4.9 million barrels was released. In November 2012 BP pleaded guilty to 11 counts of manslaughter, two misdemeanors and a felony count of lying to Congress.
11. Theranos: Blood-testing claims that were not true
Theranos raised more than $700 million and reached a $9 billion valuation at its peak in 2013 and 2014, on claims about blood tests that it could not deliver. Founder Elizabeth Holmes was found guilty on four counts in January 2022 and sentenced in November 2022 to 11 years and 3 months in prison.
12. Wirecard: 1.9 billion euros missing
In June 2020 the German payment processor announced that 1.9 billion euros in cash was missing, and it filed for insolvency on 25 June 2020. The company was dismantled later that year, and its main business unit was sold to Santander for 100 million euros.
13. Mylan and the EpiPen: Price increases on a life-saving device
The wholesale price of two EpiPens was about $100 in 2009, about $265 in July 2013 and around $461 in May 2015, with Mylan holding about a 90% market share and around $1.5 billion in EpiPen sales in 2015. The case is a lesson in what a near-monopoly on a product people cannot skip allows.
14. Coca-Cola in Plachimada: Dry wells next to a bottling plant
After the Hindustan Coca-Cola Beverages plant opened in Plachimada, Kerala in 2000, villagers said their wells ran dry and the water turned contaminated. Protests began in April 2002 and the factory was closed in March 2004. In July 2017 the company told India’s Supreme Court it did not intend to restart manufacturing there.
15. Deforestation for cheap commodities: Forests cleared for palm oil, cattle, soy and more
Agriculture caused nearly 90% of global deforestation in 2025, up from more than 80% in 2012, as forests became plantations for products like palm oil, coffee, rubber and pasture. The European Union adopted a regulation to block imports of goods such as palm oil, cattle, wood, coffee, cocoa, rubber and soy that come from deforested land.
What these cases have in common
In almost every case, the money was made first and the cost arrived years later, often as a fine smaller than the profit. The ones that ended companies (Enron, Bell Pottinger, Wirecard, Theranos) involved deception that investors or clients could no longer ignore. The rest paid and carried on.
Question: What do you think is the worst thing big business has done for money? We’d love to hear from you in the comments.
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FAQ
What is the worst thing a company has done for money?
There is no single answer, but Enron’s 2001 collapse, Volkswagen’s emissions cheating (about $33.3 billion in costs by 2020) and Purdue Pharma’s $8 billion sentencing in April 2026 are among the best documented.
Which company paid the largest fine on this list?
Volkswagen’s total costs reached about $33.3 billion by June 2020, and Facebook paid a record $5 billion FTC fine in 2019.
Which companies on this list no longer exist in their old form?
Enron went bankrupt in 2001, Bell Pottinger went into administration in 2017, Wirecard filed for insolvency in 2020, Theranos shut down, and Purdue Pharma was ordered to dissolve in 2026.
Did anyone go to prison?
In several cases, yes. Theranos founder Elizabeth Holmes was sentenced to 11 years and 3 months, and four Volkswagen executives were sentenced in Germany in May 2025.
Why did you change this list?
The original relied on claims we could not confirm and on current political disputes. This version uses cases with public outcomes such as fines, guilty pleas and settlements.
How we put this list together
We picked cases where a fine, plea, bankruptcy or settlement is on the public record, and we state the amounts as reported at the time. We left out open disputes and unproven claims.
Last updated: October 2026.
