In the early 1980s, a few years 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 all the money on himself, he decided to take half his after-tax winnings, about $60 million, and set up a foundation focused entirely on helping U.S. nonprofit theaters rediscover their boldness. His money and encouragement would inspire world-class performing arts projects, regardless of their ability to make money or find big audiences.
As lottery jackpots keep getting bigger, the potential impact of these philanthropic newcomers keeps growing. In the rarified community of people who have won more than $100 million playing the Powerball lottery — there are 95 of them — more than 10 percent have formed foundations, according to a Chronicle analysis of ProPublica records. They are underwriting everything from medical research to college scholarships for low-income students in South Carolina.
The biggest of these lottery-based foundations was started in 2022 by a couple that won a lump-sum payment of nearly $500 million. Their foundation was funded by $150 million of lottery winnings.
Most other lottery-funded foundations are far smaller, generally with assets of $10 million or less, and annual giving of $1 million or less. Notable examples include the Robert & Frances Chaney Family Foundation, which is concentrating on child welfare, as well as the Calligan Family Foundation, which has been giving to causes such as the Red Cross, Catholic Charities, and the Make-a-Wish Foundation.
For overall impact — as measured by volume of giving, asset size, and leadership — the Roy Cockrum Foundation stands out among foundations seeded by lottery money. It has given away about $25 million, funding 47 theatrical productions across the United States. Some of these plays weren’t even in the planning stages until a Cockrum grant invitation arrived. This spring, a Cockrum-financed play, “Prayer for the French Republic,” was a finalist in the Tony Awards’ best-play category.
The wins and wobbles of Roy Cockrum’s foundation amount to a case study of what’s involved when lottery winners become philanthropists. In Cockrum’s case — where a strong sense of purpose helped him overcome inexperience and turn his dream into a well-functioning foundation — Lynne Meadow, artistic director of the Manhattan Theatre Club, says, simply: “He’s a man of the theater.” What’s more, she says, Cockrum has a gift for seeing the potential in others’ ideas, and inspiring them with his support. “I regard him as exactly what a philanthropic soul should be,” she says.
A Very Specific Mission
Cockrum’s desire to be more than just an actor first took shape in a 2004 visit to London, when he saw a brilliant performance of “His Dark Materials” at the National Theatre. “It was huge; it had changing sets every second and a young audience that leapt to their feet at the end,” he recalls.
“I knew for a fact that no American theater could have put that together,” Cockrum adds. “I made a mental note that if I ever had two nickels to rub together, I would try to help American theaters do something like that.”
That moment arrived in June 2014 with Cockrum’s lottery win. During the brief period of secrecy, before he told the state lottery commission that he held the winning ticket, Cockrum reached out to Benita Hofstetter Koman, a Washington, D.C., theater consultant whom he’d known since they both were acting apprentices in Louisville. “I think I have a really good idea,” he coyly wrote. “Could you come to Tennessee tomorrow? I’m sending a plane for you.”
A plane? That didn’t square with the cash-strapped Cockrum she knew. Curious to see what was up, Koman took him up on the offer. Over dinner at a restaurant in his hometown of Knoxville, Tenn., she learned about his windfall and his desire to start a foundation that could bankroll dozens of theater directors’ most intriguing ideas.
“It was jaw-dropping,” Koman recalled. Both of them sensed that directors of top regional theaters were quietly harboring production ideas that seemed unpitchable — because regular box office and donor support couldn’t make them viable. But Cockrum Foundation money could bring those ideas to life.
Koman’s own longtime experience as a contractor with the National Endowment for the Arts gave her excellent insights into regional theaters across the United States. When Cockrum asked her if she’d like to be the foundation’s executive director and sole employee, she said yes.
Another vital early ally was Marshall Peterson, a prominent Knoxville estate attorney married to one of Cockrum’s cousins. Playing coy again, Cockrum began his first outreach call by saying: “Something’s happened. I need to talk to you.” There was an awkward pause. “I think Marshall assumed I was in jail,” Cockrum recalls.
Then Cockrum spilled his lottery-winning secret, and they were on track. Peterson guided his new client through the regulatory filings necessary to get the Roy Cockrum Foundation up and running. Delaware incorporation papers were approved in October 2014; the hiring of a back-office specialist, Foundation Source, followed soon after. In April 2015, the Internal Revenue Service confirmed the foundation’s tax exempt status, processing the lottery winner’s application in a remarkably quick 30 days. “I’d been told to expect at least six months,” Cockrum recalls.
Joining Cockrum on the foundation’s board were two theater leaders he had known for decades: Frazier Marsh, a long-time director at Actors Theatre in Louisville, Ky., and Kenneth Elliot, head of the performing arts department at Rutgers University-Camden. Elliot and Cockrum had been college roommates while studying drama at Northwestern University. Elliot also had directed Cockrum in a New York show.
“I had a very steep learning curve,” Cockrum recalls. There were moments when he considered going the donor route instead, which would have been simpler and more tax-efficient. “But I had a very specific mission in mind,” he says, “and I didn’t want to be at the whim of other people’s priorities.”
Big Works, Big Casts
By early 2015, Cockrum and Koman were ready to introduce their foundation’s approach to the theater community. Rather than hire a staff to handle waves of unsolicited applications, they narrowed the field by establishing an invitation-only approach to grant making. In a series of face-to-face meetings with artistic directors, Cockrum asked: “Is there a project you’ve dreamed of doing, but you assumed you couldn’t afford?”
Theater executives across the country just melted at his invitation. An early breakthrough came in 2015, when Robert Falls, artistic director of Chicago’s Goodman Theatre, confided that he had been hoping for years to do a staged version of Chilean novelist Roberto Bolaño’s 900-page novel 2666. Falls had gone so far as to buy the English-language dramatic rights to the book, which would soon expire if unused.
Performing this sprawling tale of literary quarrels, boxing, Prussian nobility, and quite a few murders defied ordinary business logic. It would require more than a dozen actors whizzing through 88 roles. Each night’s run might take five hours. The play might not even work in the Goodman’s main, 900-seat theater; settling for the adjacent, more intimate 250-seat hall might be wiser.
When Falls finished explaining this fragile dream, Cockrum shot back: “That’s exactly what we’re looking for!” And at that point, Falls recalls, “I got a little tearful.”
When the play opened in early 2016, with $1 million of funding from the Cockrum Foundation, critics found it astonishing but “recklessly ambitious.” Even so, Cockrum says he regards “2666" as “the model for how the foundation works.” By his standard of art for its own sake, “it was perfect. People came from all over the world to see it.”
Over the past decade, the Cockrum Foundation has seen at least 90 percent of its grants deliver the expected results. There have been a few missteps along the way, but with the largest grants ($1.5 million or so) amounting to less than 3 percent of the foundation’s total assets, the penalties have been bearable.
For example, the long-term support of the Louisville Theater’s apprentice program was forced to terminate ahead of schedule when theater officials disbanded the project. A stage adaptation of James Agee’s novel Knoxville: Summer of 1915, scheduled to open in Sarasota, Fla., in April 2020 had to be postponed when Covid hit. The project finally debuted two years later, albeit with additional financial support.
Some foundation-supported plays have trouble attracting giant audiences — but Cockrum refuses to consider those as failures. “Whether a play runs for two weeks or two years is not part of our mission,” he says. “That’s up to the artists; it’s not up to us. We’re making things happen that people assumed they couldn’t do. When they happen, we’ve succeeded.”
As Cockrum points out, the foundation’s essential purpose is to help launch productions that would not get staged for pure commercial reasons. Big, sprawling works are at the heart of Cockrum’s portfolio, and he’s proud of helping theater leaders regain the freedom to stretch beyond financially safer one- or two-actor shows.
“We prefer large casts,” Cockrum defiantly says. “We want to employ as many people as we can: as many artists and designers and actors.” A Cockrum Foundation production is practically a full-employment act for a theater community, and he likes that. After all, Cockrum knows what it’s like to live on the edge of the professional theater world, hoping that a big new play might bring a few weeks’ work.
Setting a 99-Year Plan
While there’s no official ceiling to Cockrum Foundation grants, grants to smaller venues can be as small as $100,000. “We’re keenly aware that too much money can do a lot of harm to an organization,” Cockrum says. “They can over-staff, assuming that they will stay at that level, and end up in debt. A tsunami of money is hard to manage.”
Knowing that he’s a highly adventurous investor on his own (“I buy lottery tickets”), Cockrum has turned to an outside financial firm, Morgan Creek Capital, to oversee the foundation’s investment portfolio. Slices of the portfolio focus on everything from blockchain to private stakes in startups that haven’t yet gone public. In strong years like 2021, investment gains have approached 30 percent. There have been downturns, too; overall assets today have grown moderately from Cockrum’s initial commitment of $60 million, despite a decade of steady outflows to pay for grants.
Over time, the Cockrum Foundation has become known for several areas of (unofficial) concentration. One involves bringing a wider range of drama’s classics back on stage — ranging from Shakespeare’s less famous plays to an assortment of Greek tragedies. That’s a boon for artistic directors eager to stretch beyond “Hamlet” and “Romeo & Juliet.” It also helps regional theaters be seen as nationally relevant innovators.
The Cockrum Foundation also has gravitated toward plays with strong social justice themes. These include a trilogy about the 1955 murder of Black teenager Emmett Till, as well as “Between Two Knees,” a fierce comedy about Native American land rights, and “A Prayer for the French Republic,” which looks at rising antisemitism in Europe. All won strong approval from critics.
In some cases, the Cockrum Foundation now works in tandem with other foundations and private donors to underwrite the costs of a big new production. Even so, directors say, Cockrum support is distinctive in many ways. Approvals are faster; paperwork is less, and Cockrum grants often come with stepped-up funding to cover seldom-granted wish-list items such as an extra week of rehearsal so that directors and actors can master the material more deeply.
Running a foundation isn’t easy, and some Powerball winners have wound down their attempts after a few years, according to filings with the IRS. Some have made as little as $2 million in grants before calling it quits. In such cases, writing checks to admired causes can seem a lot simpler than keeping a grant-making system running.
Big lottery winners also have to contend with a host of scammers who create fake narratives — using the winners’ names — to fool gullible people into giving away their bank information while applying for bogus grants. “It’s an ongoing scam by criminals that I have no power to stop,” Cockrum says. “Please let people know that I am not giving away $300,000 to everyone in America.”
In some cases, lottery winners’ foundations may be destined to last for one generation but no more. The Castellano Family Foundation, set up after Carmen and Alcario Castellano in 2001 won $141 million in the California state lottery, lasted 22 years. It closed in 2023 after giving away more than $10 million.
Cockrum thinks his foundation can last much longer. He’s already negotiated one age-related transition. When Benita Koman retired as executive director in 2019, a younger successor with NEA experience, Carol Ann Lanoux Lee, took over. He also has invited younger prospects to be board observers, on the notion that they will run the foundation when his generation retires.
In the year 2113, Cockrum says, his foundation’s charter calls for the board to distribute all remaining assets and cease operations. That original 99-year target is so far away that Cockrum acknowledges he won’t be around to see if it’s enforced or if the foundation goes out of business earlier. Still, he likes the notion of a century-long horizon.
“I don’t know where theater will be in 200 years,” Cockrum says, “but we hope it will be around for another hundred.”
Reporting for this article was underwritten by a Lilly Endowment grant to enhance public understanding of philanthropy. The Chronicle is solely responsible for the content. See more about the Chronicle, the grant, how our foundation-supported journalism works, and our gift-acceptance policy.
