He was bred by Bonnie Cady, and was sired by the World Grand Champion Coin's Hard Cash, out of the mare Pride's Georgia Peach.
Ridden by Day, he won the four-year-old preliminary class in the 1995 Tennessee Walking Horse National Celebration and followed up by winning the World Championship for that age division.
Following the World Grand Championship, Gilmer and Cash for Keeps made appearances at multiple horse shows across the Southeast and signed autographs at the Celebration Grounds.
At the end of the ceremony Gilmer dismounted, attached the reins to the saddle so they could not drag or catch Cash for Keeps' feet, and allowed the horse to exit the arena by himself.
[3] In 2006, five years after being retired and at the age of 15, Cash for Keeps entered the Celebration again and, ridden by Gilmer, won the Plantation Lite-Shod World Championship.