SAN DIEGO, CALIF.- 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 $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 William 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.”

Over the past decade, the Roy Cockrum Foundation has supported American theaters including the Goodman and Steppenwolf in Chicago as well as the Guthrie in Minneapolis. One production that it helped finance, “Prayer for the French Republic,” produced by Manhattan Theater Club in New York, was nominated this year for a Tony Award for best play.

Cockrum’s path to becoming a major theater benefactor was anything but typical.

He was originally drawn to acting, doing plays as a high school student in Knoxville, Tennessee, and later earning a degree in theater from Northwestern University in 1978. After stints at the Virginia Shakespeare Festival and at the Actors Theater of Louisville as an apprentice, he worked in Chicago and then New York, where he did some commercials and appeared in the cultish off-Broadway hit “Vampire Lesbians of Sodom.” He supported himself through day jobs, including waiting tables at Charley O’s in Rockefeller Center, hand modeling and proofreading financial documents.

But the grind took its toll.

“After 21 years in New York as an actor, it wasn’t as much fun,” Cockrum recalled. “And 9/11 happened, and there were lots of sirens going on all the time and I was out of work and all that was on TV were firemen’s funerals.”

Looking for respite, he went on a five-day silent retreat at Holy Cross Monastery in New York’s Hudson Valley and “got hooked.” In 2002, he became Brother Roy, entering the Episcopal monastery of the Society of Saint John the Evangelist in Cambridge, Massachusetts, becoming a postulant and a novice.

While on a 2004 visit to London, Cockrum was moved by Nicholas Hytner’s sizable production of “His Dark Materials” at the National Theater. He began thinking about how in Europe, government support of the arts makes such big stagings possible, while theater in the United States depends on commercial backers or private philanthropy.

“I thought: Should I ever have two nickels to rub together, I would try to help fill the gap that exists for nonprofit theaters in America,” he said.

It was around this time that he decided not to take the vow to remain a monk for the rest of his life, so he could return to Tennessee to care for his parents, who were in declining health. “I decided I was needed more in Knoxville than in East Africa,” he said.

It was back in Knoxville that he picked up a Powerball ticket at a Kroger grocery store — and won $259 million. “I fell to my knees,” he recalled.

What he did next was shaped by his experience in the monastery. “You live under a vow of poverty for a while and then come into a great deal of money — how you decide to spend that money is affected by that view of the world,” he said.

To collect the money sooner, he opted to take the jackpot as a smaller lump sum of $158 million (minus 25% after taxes) so he could start his foundation, which has a small board of directors and an executive director.

Cockrum has personally given to other charitable causes, including Doctors Without Borders and a religious camp for the Episcopal diocese. He is on the board of the Knoxville Symphony, where he is the primary sponsor of its Chamber Classics Series. And Cockrum has treated himself a bit, spending some of his winnings on “luxury travel” and an electric BMW iX. But the foundation’s only focus is theater.

Every board meeting begins with a reading of the mission statement and a quote from Albert Camus: “Without culture, and the relative freedom it implies, society, even when perfect, is but a jungle. This is why any authentic creation is a gift to the future.”

Tax forms show the foundation’s gifts as ranging from about $25,000 to more than $1 million. And at a time when many nonprofit theaters are trying to save money by mounting shows that require only one or two actors, Cockrum’s foundation gravitates toward large productions. “A large show means a lot of people working,” Cockrum said.

Theaters have to be invited to apply for funding. The foundation keeps up with the activities of regional theaters all over the country, and asks institutions how it might help them realize their most ambitious theatrical goals.

For the Old Globe, the answer was the “Henry VI” plays.

The Old Globe — inspired by the Globe, the London theater where a number of Shakespeare plays were first performed — opened in 1935 in Balboa Park, with performances of abridged versions of Shakespeare’s plays as part of the California Pacific International Exposition. Over the decades, it has expanded and been rebuilt, developing a strong reputation for producing new works and creating productions that wound up on Broadway, most recently “The Heart of Rock and Roll,” a Huey Lewis musical. But it remains committed to staging Shakespeare.

The theater had performed every Shakespeare play in the canon except the “Henry VI” plays. They can be a daunting challenge for many theaters because they are lesser-known by audiences, there are three plays and they require a large cast.

Edelstein, a Shakespeare specialist who took over the Globe in 2012, proposed adapting the drama into “Henry 6,” a more digestible two-part production presented on alternate nights. He wanted to use video and live music, and believed it was important to incorporate regular San Diegans, in keeping with the Globe’s ongoing community commitment “to make theater matter in people’s lives.”

More than 1,000 people ended up participating in free acting, directing and design workshops as well as making appearances in walk-on parts, video projections and recorded choral singing. And Cockrum enabled the Globe to make it all happen with infusions of money over several years totaling about $1.8 million.

“We could never put 30 people on stage without him, let alone all the community stuff,” Edelstein said, adding that Cockrum’s funds also underwrote an exhibit about the history of Shakespeare and a public art piece in the theater’s plaza. During opening weekend, Cockrum was praised by Edelstein in a toast at a preshow dinner for “reinventing how arts philanthropy works.” Many cast members thanked Cockrum at the party afterward.

Although the pandemic has taken a toll on live performance, Cockrum said he remained optimistic about theater.

“I’ve been in packed houses in Minneapolis, D.C., New York — I’m seeing people loving going to the theater,” he said. “People know what solitude is now and are keen to be out and about.”

This article originally appeared in The New York Times.