After signing with the White Sox, Drabek was assigned to the
Niagara Falls Sox in the short-season New York-Penn League where he finished 6–7 with a 3.67
earned run average (ERA) in 16 games with 103 strikeouts in innings. After pitching one game for the Single-A
Appleton Foxes, Drabek was promoted to the Double-A
Glens Falls White Sox and was 12–5 with a 2.24 ERA. On August 13, he was traded to the
New York Yankees along with
Kevin Hickey to complete an earlier deal made on July 18 for
Roy Smalley. Drabek then spent the rest of the 1984 season with the Double-A
Nashville Sounds. In 1985, Drabek returned to Double-A and spent the entire season at
Albany-Colonie in the
Eastern League and finished with a 13–7 record with a 2.99 ERA with 153 strikeouts in innings. After starting the 1986 season a with the Triple-A
Columbus Clippers, Drabek made his Major League debut on May 30, coming in relief for starter
Joe Niekro in a 6–3 loss to the
Oakland Athletics. He would spend the rest of the season with the Yankees, appearing in 27 games (21 starts) and go 7–8 with a 4.10 ERA. Following the 1986 season, the Yankees traded Drabek with
Logan Easley and
Brian Fisher to the
Pittsburgh Pirates for
Rick Rhoden,
Cecilio Guante and
Pat Clements. Drabek enjoyed his best years with Pittsburgh, from 1987 to 1992, during which time he regularly pitched over 230 innings and consistently finished in the top 10 in the National League ERA race. He went 22–6 with a 2.76 ERA in 1990 en route to winning the National League
Cy Young Award and leading the Pirates to the postseason (where they lost in the
NLCS to the
Cincinnati Reds). His 22 wins that year were a league high; it was also 7 more wins than his previous single-season mark. On August 3, 1990, while with the Pirates, Drabek had a
no-hitter broken up by a
Sil Campusano single with two out in the ninth. The hit was the only one Drabek would allow in defeating the
Philadelphia Phillies 11–0. Drabek signed as a free agent after the 1992 season with the
Houston Astros. Despite a solid 3.79 ERA and playing for a rising team, he posted a 9–18 record and led the National League in losses. He improved in the
strike-shortened 1994 season to 12–6 with a 2.84 ERA, and was named an All-Star for the first and only time in his career. When play resumed after the players' strike in 1995, however, he was unable to maintain his success and retired after the 1998 season, having compiled a 35–40 record over his final four seasons. ==Retirement and personal life==