Top 10 Greatest Pirates to Never Play in a World Series

By Jason Shetler

Here is a list of the ten greatest Pirates that never got the chance to play in the World Series during their entire careers either with the Pirates or elsewhere. 

10. John Smiley: John Smiley was a fixture in the Pirates rotation during the early 90’s. The left-hander pitched six seasons in Pittsburgh where he posted a 3.57 ERA along with a 1.19 WHIP, and finished third for the NL Cy Young award in 1991. Smiley also pitched for the Twins, Reds and Indians. 

9. Gus Suhr: Throughout the 1930’s, Gus Suhr was a key cog in the Pirates lineup. The left-handed hitting first baseman put up a .366 on base percentage with a .794 OPS and a 112 OPS+ in ten seasons with the Bucs. Suhr spent half of the 1939 and the entire 1940 seasons with the Philadelphia Phillies. 

8. Elbie Fletcher: One productive Pirate that you never hear about is Elbie Fletcher. Another lefty batting first baseman, Fletcher played his first five seasons with the Boston Braves. He then spent seven years with the Pirates, posting a .403 on base, an .815 OPS and a 128 OPS+ while being named an All-Star in 1943. Fletcher finished his career with the Braves in 1949. 

7. Richie Zisk: The Pirates had their fair share of quality outfielders during the 70’s, and Richie Zisk was certainly one of them. Zisk hit .299 along with an .842 OPS and an OPS+ of 137 in six seasons with the Pirates. He was traded to the Chicago White Sox prior to the 1977 season in a deal for Hall of Fame closer Goose Gossage. Zisk also spent time with the Texas Rangers and Seattle Mariners.

6. Frank Thomas: The Pittsburgh native played the first eight seasons of his big league career with his hometown Pirates. Thomas was a three-time All-Star, as he compiled a .275 average while putting up an OPS of .807 and a 113 OPS+. He was dealt to the Cincinnati Reds in 1959, just a year before the Pirates won their third World Series title. Thomas also played for the Cubs, Braves, Mets, Phillies and Astros.

5. Jason Bay: When the Pirates acquired Jason Bay from the San Diego Padres in the Brian Giles package back in 2003, it looked as though Bay was going to have some big shoes to fill. Those shoes wound up being a comfortable fit for him, as he batted .281 with an .890 OPS and a 131 OPS+ during his six years in Pittsburgh. The former NL Rookie of the Year was moved to the Boston Red Sox at the 2008 trade deadline. Following the 2009 season, Bay signed a mega deal with the New York Mets. After not living up to the expectations of the contract, he finished his career with the Seattle Mariners in 2013. 

4. Jason Kendall: Considered by some as the greatest catcher in Pirates history, Jason Kendall played his first nine seasons for the Bucs from 1996 to 2004. The three-time All-Star posted an on base of .387 with an .805 OPS and a 108 OPS+ with the Pirates. Kendall reached the 2006 ALCS with the Oakland Athletics, but that’s as far as he got in trying to reach the World Series. 

3. Doug Drabek: While Barry Bonds was the Pirates main piece offensively in the early 90’s, Doug Drabek was their key piece from the pitching side. He spent six seasons in Pittsburgh, posting a 3.02 ERA, an ERA+ of 118 and a 1.15 WHIP. Drabek captured the Cy Young award in 1990, becoming the first Pirates pitcher to do so since Vern Law in 1960. Despite pitching very well in the postseason, he wasn’t able to get the Pirates to the World Series in 1990, 1991 and 1992. Drabek signed with the Houston Astros prior to the 1993 season. He also pitched for the Chicago White Sox and Baltimore Orioles. 

2. Wilbur Cooper: Wilbur Cooper is one of the all-time great Pirates pitchers. Cooper pitched 13 seasons for the Pirates from 1912 to 1924 where he posted an ERA of 2.74 with a 120 ERA+, and remains the only pitcher in franchise history with 200 victories. Unfortunately for Cooper, he was traded to the Chicago Cubs just prior to the Pirates 1925 World Series championship team. 

1. Ralph Kiner: During the 1940’s, Ralph Kiner established himself as the first true power hitter in the National League. The 1975 Hall of Fame inductee had a pair of 50 home run seasons for the Pirates, and was the NL home run leader for seven consecutive years from 1946 to 1952. Kiner played eight seasons with the Pirates, as he posted a .405 on base along with a .971 OPS and a 157 OPS+. Following his tenure in Pittsburgh, he played two seasons with the Chicago Cubs and one with the Cleveland  Indians. Kiner is still one of the greatest Pirates of all-time despite never playing in a Fall Classic.





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