Bobby started playing softball in high school and would continue for 25 years on the Northwest side and suburbs. He was an outstanding center fielder and batted in most lineups 1st to 3rd because he hit to all fields. He played for the Scorpions, Wedge, Taggers, Youngbloods, March, Inmates, Dogs, Storm and Fusion. His teams competed in USSSA and ASA nationals from 1980-95. He was MVP of the 1980 Ed Kelly Tournament and in the 1982 Clarendon Midwest and Hamlin Tournaments. In 1994 he was All-American ASA Majors and 2001 ASA Class A 1st team All-American. He was also on the local professional 12 inch team but the league folded.