By 1986, Boles had risen through the ranks in his managerial career to Triple-A. Having grown up as a White Sox fan, Boles wanted the chance to coach or manage his hometown team. In , ChiSox third-base coach Jim Leyland was appointed manager of the Pittsburgh Pirates. White Sox skipper Tony La Russa wanted Boles to be Leyland's replacement, but Ken Harrelson, newly named the club's director of baseball operations, hired Doug Rader instead. So Boles departed for the Royals' organization as manager of Triple-A Omaha. After one season, he was promoted by the Royals' general manager, John Schuerholz, to director of player development.