[4] After signing, Legg was assigned to the Peninsula Pilots, the Phillies' A-level affiliate in the Carolina League.

[5] Playing alongside future Philadelphia Baseball Wall of Fame members Darren Daulton and Juan Samuel,[6] Legg appeared in 44 games, making 56 putouts and 130 assists.

Legg posted a .317 average for the season, the second-best mark among the team's regular batters (40 or more games played); he also notched his first professional home runs, hitting four to go with fourteen doubles and one triple.

[8] The Phillies shifted Legg primarily to second base for the 1984 season; he appeared in 57 games at the position for Reading[9] before a promotion to the Portland Beavers.

[9] After moving to the Oregon club, Legg continued his .241 batting pace in 141 at-bats, collecting eight doubles and one home run.

He made his major league debut against the New York Mets, entering in the seventh inning of an April 18 contest as a defensive replacement for second baseman Luis Aguayo.

[16] Legg collected the top performance of his major league career against the Pirates on September 16, hitting safely three times in five at-bats, including a double, scoring one run, and earning his first major-league RBI.

[17][18] He went 1-for-1 against the Chicago Cubs on September 29, and then hit safely twice in two consecutive games against the Montreal Expos on October 4 and 5, raising his season average to .450.

[16] Legg spent most of the 1987 season in Triple-A with the Maine Guides, for whom he batted .241 with 16 doubles, 4 triples, 4 home runs, and 30 RBI.

[5] After the 1988 season, the Phillies' Triple-A franchise moved to the Wyoming Valley in Northeastern Pennsylvania, becoming the Scranton/Wilkes-Barre Red Barons.

[28] Having stopped playing to coach for the 1994 season, Legg was activated into the minor league system by the Phillies after an injury to shortstop Kevin Stocker.

[29] After batting .298 with four doubles, two home runs, and ten RBI during the 1994 season,[30] Legg retired for good to become a coach.

[31] In 1996, Legg was inducted into the Southeastern Oklahoma State University Athletic Hall of Fame by his alma mater on January 27.

[31] In 1997, Legg was given his first managing position, leading the Batavia Clippers to the New York–Penn League finals, where they lost to the Pittsfield Mets.

He managed the Martinsville Phillies in 1998, and returned to Batavia in 1999, where the newly renamed Muckdogs lost in the semi-finals.

He led the Piedmont Boll Weevils to another semi-final defeat in 2000, and was named the Lakewood BlueClaws' inaugural manager in 2001.

[34] For the 2005 season, Legg moved to Clearwater, with the team now known as the "Threshers", taking over the manager's duties from Mike Schmidt.

[36] In 2009 and 2010, Legg and the BlueClaws staff led the team to back-to-back South Atlantic League championships.