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An Oil Wildcatter Got Rich, Then Gave Most of It Away Quietly

At Ignatius O'Shaughnessy's funeral, his 11-year-old grandson learned what the money had really done.

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David Senra · My Conversation With Patrick O'Shaughnessy, Founder of Colossus & Positive Sum | David Senra

Patrick O'Shaughnessy's father was 11 years old at a funeral crowded with strangers.

The boy went up to people he didn't know and asked a simple question. Who are you. One man said he cut the dead man's hair, and that the man had put his kids through college and bought him a house.

Other mourners had their own versions of the same kind of story. They described help the man had given them that the family had never tracked.

The dead man was Ignatius Aloysius O'Shaughnessy, known to everyone as IA, the great-grandfather of Patrick O'Shaughnessy, an investor and founder of the media company Colossus. This is the story of how a fortune was made and deliberately unmade, and why, in Patrick O'Shaughnessy's words, "our family takes great inspiration from him."

IA was the 13th of 13 children, Patrick says, and became an oil wildcatter, one of the independent prospectors who drill for oil where no one has proven it exists.

He was good at it. Patrick thinks the first well he drilled still pumps oil in the Midwest. IA grew, in Patrick O'Shaughnessy's words, into "one of the richest men in the United States," and his holdings were caught up in the breakup of John D. Rockefeller's Standard Oil empire under antitrust law. Standard Oil was Rockefeller's oil monopoly, broken up by the courts in 1911 into more than 30 separate companies.

That is when the story turns. IA did not spend the money in the way rich men are expected to spend it. Patrick says he did not care about money, did not really spend it, and "gave away basically all of it" during his own lifetime, mostly without putting his name on the gifts.

Patrick's father grew up to retell that day at the funeral. Patrick O'Shaughnessy said, "I was born on proverbial third base, or sliding into home," the beneficiary of generations of business success. But what his family talks about is not the size of IA's fortune, or the oil still coming out of the ground. It is the haircutter's children in college, and the house, and all the other gifts they are still learning about.

Questions people ask

What was the Standard Oil breakup that caught up IA's holdings?

Standard Oil was Rockefeller's giant oil trust, which controlled most American oil refining and transport. In 1911, the Supreme Court found it an unreasonable monopoly and split it into 34 separate companies, including predecessors of Exxon, Mobil, and Chevron.

Do other rich businesspeople give away fortunes anonymously?

It is rare at that scale, but not unheard of. Charles Feeney, who made billions in duty-free shops, gave away nearly his entire fortune anonymously through Atlantic Philanthropies. Chuck Schwab and others have also described large anonymous gifts, often to avoid attention or requests.