Year Inducted: 2023
Raised on the family farm, Dog Creek Ranch, west of Poteau, Okla., Caldwell had horses in his life from the beginning. However, the all-time leading owner in Remington Park history took a while to immerse himself in horse racing. A love of other sports dominated his early life.
Caldwell knew as a teenager that he eventually wanted to coach high school sports. He graduated from Panama (Okla.) High School in 1984 and began his teaching and coaching career at the same school in the fall of 1988. His focus and drive helped him handle the responsibilities to gain an associate’s degree at Carl Albert State College in Poteau and his bachelors at Northeastern State in Tahlequah, Okla.
Once on faculty at Panama, Caldwell taught a variety of history classes in addition to coaching many sports. He assisted for football, boys and girls basketball and served as the athletic director. He also led the softball program at Panama, reaching the state tournament seven years in a row. The state competition would lead him to games at the Hall of Fame Stadium, about six furlongs from the winner’s circle at Remington Park, where Caldwell would eventually take up a semi-permanent residence.
The will to win eventually led Caldwell to horse racing. He made some small private purchases and had his first taste of success with a horse named Fred Fred in the early 1990s at Blue Ribbon Downs in Sallisaw, Okla. Caldwell wanted to experience more victories in racing but juggling a family, teaching and coaching made the financial requirements for racing somewhat difficult. Visits to the winner’s circle would go on hold for a time.
Along with his brother Tommy, Caldwell discovered an opportunity, right below his feet on the family ranch. Good fortune, and the earth’s evolution, provided the Caldwells with an abundant source of natural stone, not too deep below the top soil of the ranch. The brothers started Blue Bird Stone and began extracting the natural stone, used primarily in the building of homes along with patio landscaping. The enterprise was very lucrative, allowing Caldwell to resign his teaching and coaching positions in 2001 to pursue the dream of a larger horse racing operation.
Caldwell began acquiring horses via private purchases and racetrack claims. He was involved with both Thoroughbreds and American Quarter Horses in the late-2000s. This was right after Remington Park launched its casino operation in 2005 which not only saved the track but the horse racing industry in Oklahoma.
The wins started to take place in rapid fashion for both breeds as Caldwell became a year-round force at Remington Park. His hands on owner-management style yielded his first leading owner title in the 2008 Thoroughbred Season with 13 victories. That was followed with back-to-back owner titles for the Quarter Horse season in 2009 and 2010 with trainer Matt Whitekiller. While enjoying what his racing operation was accomplishing at Remington Park, Caldwell decided to redirect his attention to just Thoroughbred racing. A full-blown stable of runners in both breeds had become too much to manage.
Caldwell won his second Thoroughbred owner title at Remington Park in 2010. He continued to accumulate the Ran Ricks, Jr. award as top owner for eight more years, running his consecutive title streak to nine, from 2010-2018. He enjoyed a record-setting season in 2016, winning 50 races, a new mark for ownership victories.
Caldwell added another pair of Remington Park titles in 2020 and 2021, giving him a total of 12 Thoroughbred season trophies at his home track. By 2015, Caldwell had ascended to the top of the all-time owner lead at Remington Park. Through 2022, Caldwell racked up 421 wins in Oklahoma City, a number that continues to grow.
While starting out primarily competing in the lower claiming ranks, the Caldwell ownership force began moving up the ladder to higher-priced claimers, hoping to step them up in class in the process. Former claimers who became Oklahoma Classics stakes winners for Caldwell include: Herecomesthemannow (2009 Sprint), Fifth Date (2012 Classics Cup), Eurobond (2017 Sprint) and Dont Tell Noobody (2020 Classics Cup).
The greatest Caldwell claim and climb story is Rated R Superstar. Claimed for $50,000 out of a race at Oaklawn Park in Hot Springs, Ark. in January 2021, the Kodiak Kowboy gelding never ran for a tag again. He had previously won two Grade 3 events in his younger days and at the age of 8, Caldwell gave his new star another chance at stakes success. Rated R Superstar become a two-time winner of Remington Park Governor’s Cup (2021 & 2022), won the Grade 3, $500,000 Essex Handicap at Oaklawn Park in 2022 and the Fifth Season Stakes at Oaklawn the same spring. His final victory for Caldwell came in the $100,000 Jeffrey Hawk Memorial at Remington in December 2022.
Through 22 starts for Caldwell, Rated R Superstar won six races, finished second in three others and third twice more. He earned more than $965,000 after the claim. Caldwell retired him at age 10, when his overall earnings had reached $1,847,397.
Through the years, the daily training chores for the extensive Caldwell operation have been handled primarily by Tommy Page, Federico Villafranco, Oscar Flores and Martin Villafranco. In addition to Remington Park, Caldwell runners can regularly be seen competing at Oaklawn Park, Louisiana Downs, Canterbury Park, Lone Star Park, Prairie Meadows and Will Rogers Downs, among others.
Entering the 2023 Thoroughbred Season at Remington Park, Caldwell had won more than 1,100 races overall with total earnings of more than $24 million.
Success secret has been his ability to evolve while the business of horse racing continues to change drastically from year-to-year.