He was a speedy second baseman, largely associated with the San Diego Padres. Originally drafted by the Pittsburgh Pirates in the 1st round of the Draft as a supplemental pick in 1982, After stealing a combined 90 bases in his two previous minor league seasons, Roberts was taken by the San Diego Padres in the Rule 5 draft in December 1985, thus being required to stay on Padres' major league roster for the entirety of the 1986 season.

As a rookie, Roberts was successful in 14 out of 26 steal attempts, and served as a pinch hitter. He spent the next two seasons in AAA baseball, where he would hit .306 in 1987 and .353 in 1988 with 10 triples in 98 games in 1987. His stolen base totals were also once again stellar, being 39 and 45 respectively, which caused San Diego to call him up at the end of 1988, where he played in 5 games, seeing time at third and second base, as well as pinch hitting.

Roberts hit .301 in 1989 with 21 steals and 81 runs in 329 at bats. He played all outfield positions, shortstop, second, and third. In 1990, Roberts ranked in the top 10 in the NL in Doubles (36), Steals (46), and Runs (104).

In 1991, Roberts again was injured limited to 117 games, but still managed to hit .281 with 26 stolen bases. In December 1991, the Cincinnati Reds sent pitcher Randy Myers in exchange for Roberts.

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