 Cash for Keeps was purchased by the Harrell Brawner family of Wynne, Arkansas in 1994 and initially trained by Sammy Day.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.In 1997 the Brawners moved Cash for Keeps to Ray Gilmer's West Tennessee stable so he would be closer to their home.