Bennie L. "Chip" Woolley Jr. is an American Thoroughbred horse racing trainer best known for conditioning the 2009 winner of the Kentucky Derby. One of the five children of Ann and Bennie Woolley Sr., he grew up in Dalhart, Texas, where his parents lived until 2019, when his father died and his mother moved to Amarillo, Texas. After graduating high school he studied for two years at Frank Phillips College in Borger, Texas. At age twenty he moved back to New Mexico to pursue a career in the horse racing industry.