Danny Caldwell on partnership with Toby Keith

Oaklawn Park news release by Robert Yates (Photo above: Toby Keith, left, at Ellis Park. He’s with the late GM Jeff Hall, who had just replaced Keith’s styrofoam with a Red Solo Cup and brought him a Budweiser, then-director of sponsorships and marketing Karen Hug and then-PR director Jennie Rees)

Video: Toby Keith visits Ellis Park in 2019 and gets his Red Solo Cup

A passion for winning horse races brought Danny Caldwell and country music superstar Toby Keith together. That passion will keep them together for the time being in spirit.

Country Bro Stables, an ownership entity Caldwell and Keith formed in 2021, has two horses entered Friday at Oaklawn – Wyfire in the third race and Bell Dozer in the sixth race. They are the first scheduled starters for Country Bro Stables since Keith died Feb. 5 of stomach cancer. He was 62.

“Listening to his songs all the way home,” Caldwell said late Thursday afternoon traveling from Oklahoma City to his Shady Point, Okla., residence. “Sitting here just remembering all the great memories we had together. It’s tough, man. Tough entering these horses and knowing that he’ll never get to watch them. But he’ll watch from above. That’s all we can hope for.”

Caldwell and Keith, both Oklahoma natives, formed Country Bro Stables in 2021 after having achieved success before their 50-50 partnership.

Caldwell topped the owner’s standings in 2014, 2015, 2016 and 2017 at Oaklawn and is the all-time leading owner at Remington Park in Oklahoma City.

Keith’s Dream Walkin’ Farms, an Oklahoma-based breeding and racing operation, has campaigned, among others, Grade 3 winners Cactus Ridge and Smack Smack and amassed 848 victories overall since 2001, according to Equibase, racing’s official data gathering organization.

Caldwell said he met Keith about 12 years ago at Remington Park and they quickly became friends, bound by their love of Thoroughbred racing and University of Oklahoma athletics.

“We were on the elevator at Remington Park, the last elevator there, going back and forth between the suites,” Caldwell said. “I had gotten in there with him before, but I never said anything. I wasn’t starstruck. Wasn’t going to bother him. Finally, he said something about, ‘I’m tired of getting beat by you’ and smiled real big. I said: ‘Well, man, I see you winning, too.’ I said: ‘I can remember what you do for the sport.’ We shook hands and have been friends ever since.”

According to Equibase, Country Bro Stables has 39 victories (the first coming Oct. 6, 2021, at Remington Park) from 264 starts and purse earnings of $993,245.

Country Bro Stables’ first of six Oaklawn victories to date came Jan. 15, 2022, with Call of Honor. The sixth – Keith’s last prior to his death – was Ghost Bayou Jan. 12.

Caldwell called Keith “great” to work with and a hands-off co-owner.

“He would always tell me: ‘Do what you do, partner,’” Caldwell said. “That was his favorite saying to me. I would run things by him occasionally. We talked at length about horse racing, of course, sports, his dad, different things. He let me run it, pretty much. He trusted me. So, he knew I was going to have our best interest. I couldn’t ask for a better partner. He was awesome. I’m going to miss him so much.”

Keith was diagnosed with stomach cancer in the fall of 2021 and his condition had worsened recently. Caldwell said he saw Keith for the last time on closing day of the 2023 Remington Park meeting, Dec. 16.

“We spoke once on the phone after that,” Caldwell said. “We’d usually talk every week, but he got to where he wasn’t calling. We were just basically texting, and I know that the texts were getting shorter and more heartfelt. So, I knew something was up.”

Caldwell said he can’t speculate about the future of Country Bro Stables until meeting with Keith’s family, but it’s business as usual now. Caldwell said Country Bro Stables has roughly a dozen horses in training.

“Racing was Toby’s passion,” Caldwell said. “Tricia, his wife, liked it, but it’s really something Toby loved. He loved the pedigrees, he loved the research and he loved watching his horses race. It didn’t matter if he was at a concert and getting ready to go on stage, he’s got his horse racing on. He’s watching. I honestly don’t know what they’ll do.”

In addition to Wyfire and Bell Dozer, Country Bro Stables has two horses entered Saturday at Oaklawn and one Feb. 15 at Delta Downs. Bell Dozer is named after Blake Bell, Oklahoma’s one-time bullish short-yardage specialist at quarterback.

“I hope (Keith’s) horses run good tomorrow and we can celebrate with a red solo cup in the winner’s circle,” Caldwell said.

“Red Solo Cup,” released in 2011, was a crossover hit for Keith, who had 95 career victories, solely or in partnership, at Oaklawn before his death. 

Keith recorded his first Oaklawn victory in 1999 and won 69 races, including two stakes, under the Dream Walkin’ Farms banner.