The late Terry Riddle rode many great horses, winning the NCHA Futurity as an owner, and frequently placed at the top of the prestigious show. In 2006, he placed third aboard Spoonful of Cheerios, a horse he bred. • Photo by Don Shugart.

Remembering Terry Riddle, Horseman

Terry Riddle won more than $2 million in the show pen, but his influence on the sport of cutting extended far beyond what did on the back of a horse.

Riddle, who died Jan. 9 at age 74, owned, bred and showed horses that would go on the be significant stallions or prolific producers in the sport. Among them was Freckles Playboy, a stallion he rode to the 1976 National Cutting Horse Association (NCHA) Futurity Open Co-Reserve Championship who became one of the all-time great Quarter Horse sires.

Memorial services for Riddle will be held at 2 p.m., Thursday, Jan. 14 at First Baptist Church in Elmore City, Oklahoma. To help slow the spread of Covid-19, the family asks that guests wear mask and practice social distancing while inside the church. 

Services also will be livestreamed on Facebook, enabling those who cannot attend to watch the services online at the Wooster Funeral Home & Cremation Services Facebook page. 

Officials at the funeral home plan to start the Facebook Live shortly before the start of the 2 p.m. service.


Born in 1946, Riddle grew up in Texas in a family immersed in rodeoing and roping, a discipline in which Riddle was quite skilled. Cutting entered the picture when Riddle married Sharon Freeman, daughter of cutting trainer Shorty Freeman and a sister to another legend in the sport, trainer Bill Freeman.

Blessed with what his brother, fellow cutting horse trainer Bill Riddle, called an “innate ability to pick a horse,” Riddle quickly was connected by some of the influential horses in the sport. There included Lenaette, a mare Riddle trained before turning the reins over to his father-in-law, who rode her to the 1975 NCHA Futurity Open Championship.

The next year, Riddle rode Freckles Playboy to the Futurity Co-Reserve Championship, just behind another all-time great cutting horse, Colonel Freckles. What’s more, Riddle had trained Colonel Freckles until Flynt, the horse’s breeder, sold the young stallion as a 3-year-old to Bob McLeod.

Freckles Playboy & Terry Riddle. • Photo by Don Shugart.

Though Riddle and Playboy got beat by Colonel Freckles in the Futurity, his brother Bill said when it came to the two sons of Jewel’s Leo Bars — his brother preferred “Playboy.”

“When Marion Flynt sold Colonel Freckles, Terry told him, he said, ‘Marion, I like Playboy better,’” Bill Riddle recalled. “Colonel Freckles won the Futurity [and] Terry was Reserve on Playboy … Playboy actually made the best sire, but they were both great horses.”

Trainer & Breeder

The list of top horses Riddle rode during part of all of their careers is vast. He won the most money aboard Playboys Madera, a 1982 gelding by Freckles Playboy that Riddle piloted to $398,947 of the horse’s $570,919 in lifetime earnings. The NCHA Hall of Fame horse, who holds the distinction of being the leading earner for his sire, later went on to serve as owner Kay Floyd’s mount during her 1988 NCHA Non-Pro World Championship.

His other top-earning horses were 2006 NCHA Futurity Open third-place finisher Spoonful of Cheerios ($204,986, by Hes A Peptospoonful) and 1990 NCHA Futurity Open Reserve Champion Smart Play ($121,074, by Smart Little Lena).

A few of the other great horses Riddle trained included Equi-Stat Elite $3 Million Sire Freckles Merada and his full brother, another Equi-Stat Elite $3 Million Sire Young Gun. Riddle also bred the stallions, who were both by Freckles Playboy and out of Lenaette.

He also spent time at the reins of future breeding stallions Docs Stylish Oak ($9 Million Sire), Hes A Peptospoonful ($8 Million Sire) Lenas Jewel Bars ($5 Million Sire) and Lizzys Gotta Player ($3 Million Sire).

Riddle bred more the earners of more than $2.2 million in his own name, and well as another $2 million together with Joe Ayres – a partnership that yielded the great mare Playboys Ruby, who won $268,441 in the show pen and went on to produce the earners of more than $1.9 million.

Horseman & Helper

In addition to breeding and showing horses, Riddle served the industry through leadership positions with the NCHA. He spent two terms as vice president (1996 and 1997), and was a member of the Executive Committee as well as serving in other capacities.

Riddle was named to the NCHA Riders Hall of Fame in 1989 and to its Members Hall of Fame in 2008.

In addition, Riddle was willing to help out his fellow cutters — even though he tried to beat them in the show pen. He hid that aspect of his personality under a gruff exterior, but it was always there, his brother Bill explained.

He was survived by his wife, Sharon, daughter Shanna Kay Riddle, son Troy Dee Riddle and wife Mendy Riddle as well as grandchildren and great-grandchildren.

“Terry was so gruff on the outside, [but] as he got older you could see a little bit [his softer side] … He didn’t like to go to funerals because he was tender hearted,” Bill said, noting the fierce competitor and confident showman wasn’t able to hide his softer side as well in recent years. “And you watch him with his grandkids – and, especially with his great grandkids the last few years – he’s a different guy.”