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An SEC filing revealed that Cook had sold the 37,500 shares on Monday as part of a Rule 10b5-1 trading plan that lets major shareholders of companies set up scheduled trades to avoid accusations of insider trading.
Cook's shares vested last Saturday after a two year waiting period. In March 2010, the executive was awarded 75,000 restricted stock units "in recognition of his outstanding performance in assuming the day-to-day operations" of Apple while Jobs was on medical leave to recover from a liver transplant. When the first half of the shares vested last March, Cook immediately sold off the batch, netting $7.02 million after taxes.
This year, Cook's tax bill for the second half of the shares came out to $9.44 million. He opted to pay by surrendering 17,322 shares at a stock price of $545.17. His profit of $11.1 million came from a series of five staggered sales throughout the day on Monday, a day that happened to see a new all-time high for Apple's stock. Shares of the company closed at $552 on Monday.