While writing, recording, and performing a long string of top country music hits since the turn of the century took up most of his hours, Toby Keith also made the time to enjoy his large Thoroughbred racing stable.

Upon the news of Keith’s Feb. 5 death at age 62, the country music singer and songwriter’s other passion was on the mind of trainer Bret Calhoun, who conditioned 2003 Arlington-Washington Futurity winner Cactus Ridge for Keith’s Dream Walkin’ Farms. Calhoun noted that as an owner and breeder Keith oversaw a large stable.

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“If you look at his operation as a whole, I think he just wanted to enjoy them as much as he could,” Calhoun said. “He had big numbers. He had them at all different levels. Everybody always wants good horses and I think that mattered to him. But I just think he enjoyed having action. He liked numbers and action.”

Keith enjoyed researching potential matings and it was not unusual to see him at sales. But the excitement of the track captured Keith’s imagination.

“He would try to work his schedule where he could be at some of the races whether he was playing concerts and get to fly in,” Calhoun said. “He would always try to make it to some of the bigger races.”

The musician, who was born Toby Keith Covel, began buying horses to race in the late 1990s and breeding shortly thereafter. He later became a Breeders’ Cup ambassador.

“We were extremely saddened to learn of the passing of Toby Keith today,” Breeders’ Cup said in a release. “In addition to his tremendous accomplishments in the music and entertainment world, Toby was a longtime Breeders’ Cup ambassador and an enthusiastic Thoroughbred owner, breeder, and fan who greatly enjoyed attending the Breeders’ Cup World Championships. Along with his legion of fans, we will miss him very much and express our deepest condolences to his loved ones.”

Toby Keith at Oaklawn Park in 2017. (Eclipse Sportswire)

His first horse, Jack Branch, won on first asking in a Dec. 13, 1997, maiden special weight at Remington Park. Besides Cactus Ridge, a son of Hennessy who would stand in Kentucky and then Oklahoma, Keith also campaigned 2016 Grade 3 winner Smack Smack, who was trained by Don Von Hemel.

At his peak, Keith had several hundred horses he was racing, breeding, or selling under his Dream Walkin’ Farms banner. Not counting partnerships, Dream Walkin’ Farms won 848 races from 6,587 starters with $18,648,853 in earnings in Equibase statistics that date back to 2001. In 2016, his operation ranked 12th in owner wins. Dream Walkin’ Farms had two other top-15 finishes for wins (2015 and 2021) and since 2012 has consistently ranked in the top 100 by earnings and/or wins.

“Music is something that can last longer than a sports career if you can stay successful,” Keith told BloodHorse in 2015, “but if a guy ever does decide to hang it up, he really has to find something else that thrills him. And the horse racing business has always thrilled me that much.”

Despite a bobble at the start, Cactus Ridge kept his perfect record intact with a three-length victory in the Grade 3, $150,000 Arlington-Washington Futurity on the closing day card at the suburban Chicago racetrack. With Eddie Martin Jr. in the irons, the Bret Calhoun-trained colt established a stakes record time of 1:35.44 for the mile on a fast track, eclipsing the 1:35 4/5 standard set by Secret Hello in 1989.

Toby Keith in July 2023 (Eclipse Sportswire)

“It was it was a lot of fun, it really was,” said Calhoun of working with numerous horses for Keith. “He was a guy that really, really loved the business. He was really involved in it, he loved trying to figure out breeding and crosses, and nicks; he loved that kind of stuff. He loved going to the races. He loved watching his horses. He liked all facets — he loved the buying, selling, racing, breeding.”

Smack Smack would finish as his top earner at $986,419. By 2005 Kentucky Derby runner-up Closing Argument, Smack Smack posted 10 wins, seven seconds, and nine thirds from 37 starts, including a victory in the Grade 3 Cornhusker Handicap in 2016. Other notable runners included Three Chords, Ghost Locket, and Seeking Ms Shelley.

Calhoun said he had not spent much time with Keith recently but fondly recalls the time they did spend together at Remington Park shortly before Keith was diagnosed with cancer in June 2022.

“Obviously, the music industry [Keith’s death] is a big loss for them. It’s a big loss for the horse racing industry because he was a big promoter for the horse racing industry. He just really loved it,” Calhoun said.