When Roy Cockrum, a one-time struggling actor and a former monk, won a $259 million Powerball jackpot in 2014, he decided to splurge on something a bit out of the ordinary: supporting nonprofit theater.

He set up a foundation that has given away $25 million to 39 American theaters so far, which is why he found himself the other night at the Old Globe in San Diego. He was there to watch the premiere of a production he supported to help the theater reach a milestone: a large-scale staging of the only Shakespeare play it had yet to produce, an adaptation of the somewhat rarely performed three “Henry VI” plays.

“The question I put to artistic directors is, ‘Is there a project you’ve always dreamed of doing that you couldn’t afford?’” Cockrum, an apple-cheeked, snowy-haired 68-year-old, said in an interview. “To help artistic directors dream bigger than they would otherwise.”

At a time when nonprofit theaters across the country are struggling with rising costs, fewer subscribers, smaller audiences and dwindling corporate philanthropy, Cockrum’s generosity stands out.

“He’s an inspiration to other philanthropists at a time when our field is really struggling and where we need innovative ideas about philanthropy to try to move the field forward,” said Barry Edelstein, the Old Globe’s artistic director. “We’re not going to solve the structural financial problems facing the sector through Bernie Sanders-style $27 contributions. It’s going to take really significant infusions at the scale that Roy is doing them.”