The transactions were revealed in a regulatory filing Thursday, which showed that Cook had acquired and sold more than 5 million shares of the iPhone maker.
As head of the world's most valuable company, Cook has received lofty stock awards in recent years.
One of the incentives was tied to Apple's performance in the S&P 500 over the past three years. The stock award was triggered this week because the firm was one of the index's top performers, generating shareholder returns of nearly 192% from August 2018 to 2021, it said in a filing.
Apple is the world's most valuable company, with a market cap of $2.4 trillion. Its stock is up about 11% so far this year.
Cook's windfall came just days after he also donated 70,000 Apple shares (worth about $10 million) to charity, according to a separate regulatory filing Tuesday. It did not disclose the name of the recipient.
Cook joined Apple in 1998 and served in a variety of senior roles before assuming his current position, including chief operating officer and executive vice president of worldwide sales and operations. He was named CEO in August 2011, after co-founder Steve Jobs famously stepped down. Jobs died weeks later from complications of pancreatic cancer.
Prior to joining Apple, Cook worked at Compaq and IBM.
In 2014, Cook made history for becoming the first Fortune 500 CEO to come out as gay. The following year, he pledged to donate most of his wealth to charity.
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