In 1991, Street started a successful career as a settlement planner, owning his own business, The James Street Group. He had five sons, including three who won National Championships playing baseball for Texas. His oldest son Ryan Street, from his first marriage attended Texas Tech. Street and his wife of 32 years, Janie Street had four sons, former Longhorn and Los Angeles Angels closer Huston Street, former Longhorn and minor league pitcher Juston Street, former Longhorn pitcher Jordon Street and Pepperdine infielder Hanson Street who earned an MBA at the Red McCombs School of Business at the University of Texas. Juston Street went into acting, and one of his first film appearances was playing his father, James Street, in the film "My All American".