
10. Juan Marichal: He pitched from 1960 until 1975 and was named an all-star 9 times. Marichal led all of MLB in wins in 1963 and 1968 and threw over 300 innings in both those seasons as well. Somehow, he wasn’t even considered in the top 10 of Cy Young voting either season.
9. Mark Langston

Langston pitched in MLB for 16 seasons and was a 4-time all-star and 6-time Gold Glove Award winner. He finished inside the top 5 Cy Young award voting only once in his career, though, in 1987, highlighted by 14 complete games, 19 wins, and 272 innings pitched.
8. Adam Wainwright

Wainwright spent his entire career from 2005 until 2023 pitching for the St. Louis Cardinals. He finished in the top 3 of Cy Young Award voting three times (2009, 2013, and 2014). He tallied 19 wins in both 2009 and 2013 as well.
7. Jimmy Key

Key pitched in MLB for 15 years with 3 different teams, all in the American League. He finished in the top 5 in Cy Young Award voting three times and top two twice. His best season was arguably in 1987 when he posted a 2.76 ERA, 17 wins, 261 IP, and a 1.05 WHIP.
7. Jim Kaat

Kaat pitched in MLB for 25 seasons and won 283 career games. He might have been most well known for his stellar defense on the mound, winning 16 gold glove awards. However, he was only in the top five of Cy Young Award voting one time in 25 years.
5. Bert Blyleven

He pitched in MLB for 22 seasons and for five different teams. Blylevin finished in the top 5 of Cy Young voting three times and in the top three twice (back-to-back years in 1983 and 1984).
4. Jon Lester

Lester was one of the better big-game playoff pitchers of his generation and won World Series rings with two of the most storied franchises in MLB history (Red Sox and Cubs). He was in the top 10 of Cy Young voting four times in his career, including three finishes in the top five. He was the runner-up in 2016, the season he helped the Cubs win their first World Series since 1908.
3. Mike Mussina

Mussina pitched in MLB for 18 years, half with the Orioles and half with the Yankees. He never won a World Series, and despite finishing in the top 5 of Cy Young voting six times, he never won the award and only finished in the top 3 once.
2. Curt Schilling

Schilling had an incredible 20-year career in MLB, winning multiple World Series and being named an all-star 6 times. In a four-season span from 2001-2004, he finished 2nd in Cy Young Award voting, twice in the NL and once in the AL.
1. Nolan Ryan

You would think that a guy who pitched for 27 seasons, winning 324 games and struck out 5,714 batters, would have won at least one Cy Young in his career. Well, he didn’t win one, even though he finished in the top five of voting six different times, including three finishes in the top three.
