Ashby attended Park Hill High School in Kansas City and played baseball with the Crowder Roughriders at Crowder College. He was signed as an undrafted free agent in 1986 by the Phillies, with whom he made his Major League debut in 1991.\n', '

On June 15, 1991, Ashby struck out three batters on nine pitches in the fourth inning of a 3–1 loss to the Cincinnati Reds; Ashby became the 15th National League pitcher and the 24th pitcher in Major League history to accomplish the nine-strike/three-strikeout half-inning. He was acquired by the Colorado Rockies in the 1993 expansion draft, but after compiling an 0–4 record with an 8.50 ERA, he was dealt to the San Diego Padres at the end of the season.\n', '

Despite injuries to his shoulder, elbow and back, Ashby saw the greatest success of his career with the Padres. His most productive season came in 1998, when he helped the Padres reach the World Series with a 17–9 record and a 3.34 ERA. He was also a member of the 1998 and 1999 National League All-Star team. In eight seasons with the Padres, Ashby compiled a 70–62 record with a 3.59 ERA.\n', '

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