In the early 1980s, soon after graduating from college, Roy Cockrum was trying to make it as an actor in New York. He was hanging on by his fingernails, getting paid $40 a show for two supporting roles in the off-Broadway comedy “Vampire Lesbians of Sodom.”
To cover his rent, Cockrum would pick up extra cash doing financial-document proofreading at 2 a.m. Risk factors, operating margins — the terms washed over him endlessly. “I was both without money — and around money a lot,” he recalls.
Then, in 2014, at age 58, Cockrum’s luck abruptly changed.
After decades of character-actor obscurity, Cockrum won America’s Powerball lottery, collecting a lump-sum check for $153 million. Instead of spending it all on himself, he decided to take half his after-tax winnings, about $60 million, and set up a foundation focused on helping U.S. nonprofit theaters rediscover their boldness.
Over the past quarter-century, 95 …