Chili Cole grew up in San Antonio, Texas. As a youth he started his cowboy career riding stick horses. After stick horses, Chili graduated to riding milk calves then bareback broncs, bulls and steers.
As an early member of the Cowboy’s Turtles Association, he rode bulls or bareback broncs at Ft. Worth, Houston, Cheyenne and Madison Square Garden in New York City.
In the 1950’s Chili moved to San Angelo and in 1953 formed the Westbrook-Cole Company an agricultural loan firm. He soon became active in the San Angelo Rodeo & Stock Show where he rose to be its’ president, a position he held for over 20 years.
Chili started the Invitational Steer Roping when there was no Steer Ropings in Texas. It is still an annual event in San Angelo. He was the main force in promoting and building the coliseum which was the first in the area. His son C. A. “Chip” Cole still heads the business.