Philanthropist and oilman T. Boone Pickens, who appeared on the Chronicle’s annual list of the biggest donors five times over the years, died today at age 91.

With a net worth that once stood at just over $1 billion, the brash Texan had whittled down his fortune by giving at least $790 million to nonprofits since 2003, according to a Chronicle tally.

Some of his biggest gifts went to his alma mater, Oklahoma State University. Pickens pledged at least $500 million to the institution over the years and said those pledges would be fulfilled upon his death. A 1951 graduate who majored in geology, Pickens founded Mesa Petroleum, an oil company, in 1956, and BP Capital Fund Advisors, an energy-investment firm, in 1996, gaining a reputation as a rabble-rousing corporate raider.

Some of his gifts to the university caused controversy. In 2006, he pledged $165 million to the athletics department. The university invested all of the money, as well as other donations, in Pickens’s hedge fund. The value of the investment plunged, and Pickens ended up donating an additional $63 million to the athletics department in 2008 to make up for the shortfall and complete projects started under the original gift.

In 2010, he pledged an additional $100 million to endow scholarships for students who otherwise could not afford to attend.

He also gave to other organizations, including $160 million to establish a foundation in 2006. (He originally said he was giving $135 million but later told the Chronicle that he had added $25 million more.) Pickens said at the time that he would focus most of his grant making on charities and causes in Oklahoma, where he was born, and Texas, his longtime home.

Through the foundation, he gave mainly to health and medical research, treatment, and services; aid for troubled children; entrepreneurship; education and athletics; corporate health and fitness; and conservation and wildlife management. He poured an additional $156 million into the foundation in 2007.

Pickens sometimes placed unusual restrictions on his donations. In 2007, he contributed $50 million apiece to two Texas medical institutions and stipulated that the money had to be invested and grow by at least 10 times until the organization could spend any of it. If they didn’t reach that benchmark by 2022, Pickens would redirect the money to another nonprofit.

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Maria Di Mento directs the annual Philanthropy 50, a comprehensive report on America’s top donors. She writes about wealthy philanthropists, arts organizations, key trends, and insights related to ultra-high-net-worth donors, among other topics.