As of the 2008 season, four pitchers in MLB history have won 4 or more Cy Young Awards: 1) Roger Clemens - 7 (1986, 1987, 1991, 1997, 1998, 2001, 2004)
2) Randy Johnson - 5 (1995, 1999, 2000, 2001, 2002)
3) Steve Carlton - 4 (1972, 1977, 1980, 1982)
4) Greg Maddux - 4 (1992, 1993, 1994, 1995)
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Fernando Valenzuela won both the National League Cy Young and Rookie of the Year Awards in 1981. "El Toro" started the season with an 8-0 record. The season was then interrupted by a player's strike. He finished the season at 13-7 with an ERA of 2.48 and 180 strikeouts.
That would be Roger Clemens who has won seven (1986, 1987, 1991, 1997, 1998, 2001, 2004).
Koufax won three Cy Young Awards, 1963, 1965 and 1966. Starting in 1956 when the Cy Young Award was created, only one award was presented for the entire Major Leagues. After 1966, both the American and National Leagues presented Cy Young Awards.
As of the 2008 season, no Cincinnati pitcher has won the Cy Young Award.
Roger Clemens won seven Cy Young Awards during his career.
Tom Glavine has won two Cy Young Awards, one in 1991, and the other in 1998.
The Cy Young award is given to the best pitcher in baseball, so if you won this award you would continue to play as a pitcher.