Obituary: Horse Racing 'Thrilled' Musician Keith

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

Upon the news of the Feb. 5 death at age 62 of the country music singer and songwriter, Keith's other passion was on the mind of trainer Bret Calhoun, who conditioned 2003 Arlington-Washington Futurity (G3) winner Cactus Ridge . for Keith's Dream Walkin' Farms.

"If you look at his operation as a whole, I think he just wanted to enjoy them as much as he could," said trainer Bret Calhoun. "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.

"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." 

His first horse, Jack Branch, won on first asking in a Dec. 13, 1997, maiden special weight at Remington Park.

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 only to 2001. In 2016, it was 12th in owner wins. Dream Walkin' Farms had two other top-15 finishes for wins (2015 and 2021).

One of the more notable horses that Calhoun trained for Keith was Cactus Ridge. The son of 1995 Breeders' Cup Juvenile (G1) runner-up Hennessy was went 4-for-4 as a 2-year-old. He capped his racing career by winning the 2003 Arlington-Washington Futurity (G3) by three lengths. 

"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."

Keith's top-earning runner was Smack Smack ($986,419). By 2005 Kentucky Derby (G1) second Closing Argument , Smack Smack was 10-7-9 from 37 starts, including a victory in the 2016 Cornhusker Handicap (G3)

Other notable runners are 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 (his 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.