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Oh, lucky man: $259M Powerball winner talks about his life as an actor, promoting the theater, and yes, that moment he realized he’d won the big one

Roy Cockrum won the jackpot in June 2014. He immediately created a foundation to help promote non-profit theater.

KNOXVILLE, Tenn. — Lucky is the man who gets to pursue a passion that not only gives him satisfaction, but also creates work for a profession, allows dreamers to dream and entertains an audience night after night.

Roy Cockrum is profoundly blessed in that regard.

The Knoxvillian created a foundation that hands out millions of dollars to non-profit theater programs from California to Florida and all points in between. And it all came about because of the unlikeliest of events, the longest of long-shots: winning a $259.8 million Powerball lottery in 2014.

Cockrum sat down this summer with WBIR to talk about his life, his work to promote the theater and the September kickoff at the Clarence Brown Theatre of the musical "Knoxville," which he helped fund.

Cockrum does not seek attention. Since winning the lottery, he's preferred to stand to the side, quietly helping out theater programs and savoring their artistry.

Credit: WBIR
Roy Cockrum and Ken Martin talk with WBIR's Robin Wilhoit.

"It's one of the personal ambitions of my life to really help people see as much theater as possible and on a high level, and so that's why, when I had the opportunity, I wanted to inspire non-profit theaters all over the country to do the best work they could do, because that's what matters -- the best they can do and not be limited by funding."

Joining 10News in the conversation was Ken Martin, artistic director of the Clarence Brown. Martin said audiences are in for a special treat this summer when they go to see "Knoxville," based on the Pulitzer Prize-winning James Agee story of the loss of his father in a Clinton Highway car crash in 1915.

Rehearsals started this week. Single-ticket sales begin Aug. 5. The show debuts Sept. 4.

It's a universal story conceived by a first-rate creative team, Martin said.

"It is a play about family. It is a play about faith. It's a play about grief, about growing up," he said during the interview on the Clarence Brown's main stage on the University of Tennessee campus.

"I don't think that there is anybody who can come and see this and not see some moment of themselves in it."

But the musical might not have been produced and it wouldn't be coming to Knoxville if it weren't for a former actor and monk who had a life-changing day when he checked his quick-pick lottery numbers.

Credit: Powerball
The winning June 11, 2014, drawing.

JACKPOT

On Wednesday, June 11, 2014, five Powerball numbers -- 14-18-28-33-49 -- and a red Powerball of 23 popped out of the air-blown plastic bowl. He didn't know it at that moment, but Roy Cockrum, age 58, was a millionaire.

The next morning, Cockrum checked his numbers. He'd purchased the ticket at a local Kroger.  At first he thought he'd won $500, a delight in itself.

"And then I said, Wait a minute," he recalled.

He saw that he'd matched another number...and then another number. And the realization hit him.

"I literally fell to my knees," Cockrum said. "The tsunami of what had happened really washed over me."

Credit: WBIR
WBIR spoke with Martin and Cockrum on the stage of the Clarence Brown Theatre in July. The play opens Sept. 4. Single tickets go on sale Aug. 5.

But he still had to take his mom, Mildred, to a medical appointment. So he tucked the winning Powerball ticket away, picked up his mom and headed to University of Tennessee Medical Center for her appointment.

He said he walked around all morning, keeping this massive secret all to himself. Then it was time to leave the hospital campus.

The usual routine called for him to take his mom to a bench to wait while he retrieved the car. Then he'd swing by and pick her up.

Except he messed up this time.

"So I took her out and I put her on the bench and got the car. I was across the bridge on Alcoa Highway before I realized I'd forgotten to go pick her up. I was so discombobulated."

And he was a winner. 

"I didn't explain to her for the longest time why she had to wait so long" on that bench, he said, laughing.

The $259.8 million ticket had a cash-out value of $153 million, which Cockrum elected to take.

Credit: Roy Cockrum
Roy Cockrum and his mom, Mildred

CREATING A 100-YEAR FOUNDATION

Cockrum quickly set to work planning what to do with the money, a lot of it anyway. He wanted to create a foundation to help non-profit theater in the U.S.

He'd always loved the theater. As a sophomore at West High School, he'd been part of the cast of "1776" performed on the CBT stage in 1972.

Then he'd gone on to study theater at Northwestern University in Evanston, Ill. He had a long career as an actor.

"The theater has been my home most of my adult life," he said.

Later, he became a monk, during which he took a vow of poverty. While on a religious retreat in England, "Brother Roy" saw a production at the National Theatre in London of "His Dark Materials". He was struck by the size of the production and the realization that no American non-profit group could have afforded something so ambitious.

He vowed in that moment in 2004 that if he "ever had two nickels I could rub together," he'd do something about it.

Winning the lottery 10 years later made that possible.

With the help of two people, close friend Benita Hofstetter Koman and Knoxville attorney Marshall Peterson, Cockrum began to set his plans in place. Peterson helped handle the legal work; Hofstetter Koman became the first executive director of the Knoxville-based foundation.

Carol Lanoux Lee directs it today. The foundation was created to sunset at the 100-year mark, decades into the future.

"We just celebrated our 10th anniversary," Cockrum said. "And we've given away millions and millions of dollars. I'm just thrilled that we've been able to do that."

Credit: Roy Cockrum
Roy Cockrum, headshot circa 1995, from his acting days.

Foundation assets were listed at more than $60 million in a recent tax filing. Applications for grants are accepted by invitation only.

Tax records show grants have gone to the Actors Theatre of Louisville; the Old Globe Theatre in San Diego; a Yale University School of Drama production; the New York Theatre Workshop; the Mosaic Theater Company of DC; the Berkeley Rep Theatre in Berkeley, Calif.; and the Goodman Theatre in Chicago, among many others.

It helped with a more than $500,000 contribution so that the Clarence Brown Theatre and the Knoxville Symphony Orchestra could stage "Candide" in 2018, tax records show. It also supported the 2023 project to bring cellist Yo-Yo Ma to East Tennessee.

And it helped the Asolo Repertory Theatre some five years ago when Cockrum's old friend and Northwestern teacher, Frank Galati, told him he had his mind set on turning Agee's story into a musical.

"KNOXVILLE"

The pandemic interrupted the Sarasota, Fla.-based Asolo's preparation of "Knoxville", but it persevered. The production includes musical numbers from the Tony Award-winning team of Stephen Flaherty and Lynn Ahrens.

Galati wrote the book and directed the Florida production. The Asolo staged it in 2022. Galati died at age 79 in January 2023.

Soon after arriving at UT in 2022 to take on the job of artistic director, Martin said an advisory board member who had seen the Florida production demanded to know when he was going to bring "Knoxville" to Knoxville. 

That started the long process to ultimately bringing the musical -- thanks to Cockrum -- to the Clarence Brown as its season opener. You can learn more about the performances here. Many who took part in the Asolo's production will be here in Knoxville.

"I'm thrilled that it's happening, absolutely thrilled," Cockrum said. "What could be more appropriate -- to have this play happen right here just blocks from where the events of the play actually happened?"

Credit: WBIR
CBT's Ken Martin

While Galati was writing the script for the play, he visited Knoxville. Cockrum showed him around key sites relevant to the book. At first, Cockrum told Galati he was dubious about the idea. But he also knew that turning a classic book into a play was a challenge his old friend relished.

It was also exactly the kind of project that the Cockrum Foundation likes to support, he said.

What Agee created in his book has been successfully interpreted and produced for the stage, Martin said.

Considering all the work that's gone into the musical itself, the loss of Galati, the participation in Knoxville of many of the same people who took part in the Asolo production as well as the expected attendance of others from the Asolo, Martin said he expects opening night to be "a moving moment."

"It's going to be a very emotional evening for audiences that didn't know Frank and for audiences that did," he said.

Credit: WBIR
The costume shop at the Clarence Brown Theatre, which is staging "Knoxville" in September. Philanthropist Roy Cockrum is funding the production.

Said Cockrum: "This is in a way a new opening for this play that really matters and really is a next step for the life of this play."

Who knows what theater in the broader sense will look like by the time the foundation closes. But Cockrum said he's looking forward to what comes next, and he's happy with the quality of the work the foundation so far has supported.

Martin said Cockrum has done much for the theater industry.

"It's really heartwarming to know -- it's more than heartwarming -- it's wonderful to know that there is somebody out there that is supporting these big dreams and these big stories that need to be told, that should be told," Martin said, turning to Cockrum. "So thank you."

"That's what we're here for," Cockrum replied.

Who knows what lies ahead for Cockrum himself. Considering how remarkable his life has been so far, it has all the makings of a play itself.

Cockrum grins.

"You're not the first person to ask that question, and, uh....stay tuned," he said.

Credit: WBIR
Roy Cockrum grew up in Knoxville and graduated from West High School.

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