Bobby, a Blairsville native, played baseball at Blairsville High School from 2010-2013. He was a three-time Indiana All-Gazette team member, All Heritage Conference player and the captain of the 2013 PIAA District 6 champion Blairsville Bobcats.
After High School Bobby went on to play at Saint Vincent College before transferring to Westmoreland County Community College. While playing the corner infield, outfield, and pitching for the Wolfpack, he was voted the Most Valuable Player on his team by his teammates and coaches. He was named first team All-Conference, first team All-Region, All-Region tournament team and earned All-Region academic honors as well.
After WCCC Bobby had the opportunity to continue his athletic career at California University of Pennsylvania. Playing mostly in the outfield while at CalU, but was often seen on the mound as a relief pitcher. In Bobby's senior year he hit .375 and was named a PSAC scholar athlete.
Bobby played in the Beach League in Myrtle Beach, SC in 2014. Johnstown AAABA in 2015, where he finished third in the batting title race, while earning a spot on the All-Star roster as a utility player. Bobby played in the Great Lakes Summer Collegiate League in 2016 for the Richmond Jazz in Richmond, IN, where he also earned All-Star status, being the only division 2 All-Star in the league.
Bobby previously coached at his alma mater, California University of Pennsylvania and helped the Vulcans set a new record for most wins in a single season back in 2019.