Once America's seventh-largest company, Enron used systematic accounting fraud and special purpose entities to hide billions in debt, wiping out $74 billion in shareholder value when it collapsed in 2001. This was 40% more devastating to shareholders than the $64.8 billion lost in Madoff's Ponzi scheme (#1) on a percentage basis, as Enron's stock plummeted from $90 to under $1 per share. The fraud involved over 3,000 offshore entities and falsified $7 billion in earnings, enabling the company to hide $30 billion in debt while executives cashed out $1.1 billion in stock before the collapse.

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