When we think of the greatest pitchers of all-time, we think of guys like Greg Maddux, Tom Seaver, and Pedro Martinez. They are amongst the all-time greats not only for how they dominated the game, but for the longevity in which they did it. They dominated an entire era of baseball. When comparing players, there is an argument that always seems to come up as to whether long term productiveness is more significant than sheer dominance in a small amount of time. Obviously, the pitchers I listed above are examples of players who dominated for long periods of time.
However, think of other athletes like Bo Jackson. Many consider Bo Jackson to be the greatest athlete of all-time because of how freakishly athletic he was, yet his NFL career only spanned four seasons with one Pro Bowl appearance. There are many factors that can go into someone's career being derailed. The most frequent cause is injuries, but I think the fact that there are so many players who were only elite for a small amount of time is a testament to how sports are just as much mental as they are physical.
Some of the pitchers on this list did in fact have long careers at a high level. Some of them just never pitched at a high level ever again. This is not saying that the ones who did in fact have great careers weren't great. Those pitchers simply had a season where they won the Cy Young Award, and it was far greater than any other season they ever had. What all of these pitchers have in common is that they won the Cy Young and were the best pitcher in the league for a season, but never matched that level ever again.
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15 Chris Carpenter
It is unfortunate that Chris Carpenter is on this list because his career was completely derailed due to injuries. It actually took him a while to establish himself in the MLB, as he struggled in his first six seasons with the Toronto Blue Jays. After Toronto, he joined the St. Louis Cardinals and became a dominant pitcher, winning the Cy Young Award in 2005. He followed his Cy Young year with another great year, however, he missed the next two seasons entirely due to elbow injuries. The injuries continued to persist throughout his career and eventually forced him to retire.
14 John Denny
It wasn't until John Denny's 12th season when he won the Cy Young Award. He had a very up and down career up until then and his career ERA was 3.81. In 1983, while pitching for the Philadelphia Phillies, he compiled a 19-6 record with a 2.37 ERA in 242.2 innings pitched. It was a dominant performance, and he followed it with an decent year. However, the next two years would be his last in the MLB, and his ERA in those seasons would be 3.82 and 4.20.
13 Bartolo Colón
It seems like everyone forgot that Bartolo Colon was once a young pitcher who could pump out fastballs upwards of 95 mph. Still in the MLB at almost 43 years old, Bartolo Colón now has a cult following because of his old age and large 285 lb frame. Bartolo has bounced around the league and has been on seven different teams. He won the Cy Young Award in 2005 with the Los Angeles Angles by leading the league with 21 wins and posting a 3.48 ERA. He is clearly still an effective pitcher as he is still in the league today, but aside from one season in 2013 with the Oakland Athletics, he hasn't received any Cy Young votes since.
12 Doug Drabek
Doug Drabek is one of those pitchers who seemed to have the make-up of a pitcher who would be talked about as an all-time great. He had great mechanics and was an incredibly smart pitcher, and it led him to winning the Cy Young Award in 1990 while playing for the Pittsburgh Pirates. He had a very solid span of pitching from 1988-1994, where he had a terrific 3.02 ERA. However, he completely fell off after that stretch and the last four seasons of his career he posted a horrendous 5.40 ERA.
11 Jack McDowell
"Black Jack" McDowell had a great first half to his career while pitching for the Chicago White Sox. He was an All-Star for three consecutive years from 1991-1993 and won the Cy Young Award in '93 by leading the league in wins with 22 and posting a 3.37 ERA. The following season, his stats took a slight dip and his ERA went up to 3.73. He was then traded to the Yankees, where he infamously gave the crowd the middle finger when they booed him after a poor start. He then spent the last four years of his career with Cleveland and Anaheim, where he posted a 5.27 ERA in that span.
10 LaMarr Hoyt
LaMarr Hoyt was a 6'3" right-handed pitcher who anchored a great Chicago White Sox pitching staff in the early 1980s. He won the Cy Young Award in 1983 by leading the league with a whopping 24 wins. Remarkably, he led the league in losses the following year, posting a 13-18 record. He was then traded to the San Diego Padres, where he began to pitch like the Cy Young Award winner he once was. Unfortunately, Hoyt's career fell apart in the offseason when he was arrested twice for drug possession. After entering rehab, he returned to the MLB where he posted even worse numbers. He was then arrested again for drug possession and spent 45 days in jail. A fourth drug arrest in 1987 ended his MLB career at the age of 32.
9 Bob Turley
Bob Turley was an integral part of the Yankees teams that won the World Series in 1956 and 1958. They were teams that featured future Hall of Fame players Mickey Mantle, Whitey Ford and Yogi Berra. Turley was a big pitcher standing at 6'2" and weighing 215 lbs. He had a very successful start to his Major League career and won the Cy Young Award in 1958. However after that season, Turley, who seemed to be on track to the Hall of Fame, began to play worse and worse. His ERA in the five seasons after he won the Cy Young was a very pedestrian 4.19.
8 Mike Flanagan
Mike Flanagan had a great start to his career. Once he solidified his spot in the Baltimore Orioles' starting rotation, he became an absolute workhorse. He pitched 1033.1 innings in his first four years as a starter and won the Cy Young Award in 1979. Pitching a complete game was a regular occurrence for him. He managed to have a very lengthy career, however, he never was able to maintain that same durability that he had early on. He had a lot of seasons cut short by injury and he never received a single Cy Young vote in the 15 seasons he played after winning it.
7 Ron Guidry
Ron Guidry being on this list may shock a lot of people. He is an incredibly accomplished pitcher who finished top-five in Cy Young voting four different seasons. His number 49 is now retired by the New York Yankees. His one Cy Young Award came early in his career in 1978, where he had an incredible 1.74 ERA in 273.2 innings pitched. Guidry remained in the MLB for another 11 seasons, all with the Yankees. His ERA was under 3.00 only twice in that span, and it usually fluctuated around 3.50, even going over 4.00 for a couple of seasons. Guidry was a good pitcher for a very long time and had one season that was among the greatest ever. Had he been able to maintain that same level from his Cy Young year, he would easily be in the Hall of Fame today.
6 Vern Law
Vern Law was a member of the legendary 1960 Pittsburgh Pirates that defeated the Yankees in seven games to win the World Series. That season happened to be the year that Vern won the Cy Young Award and it seemed as though he had turned a corner in his career. Prior to that 1960 season, Vern Law had already been in the league for eight seasons, but his ERA was just 3.98. Vern was unable to maintain the level he achieved after his Cy Young year and went back to being just an average pitcher.
5 Éric Gagné
Eric Gangé actually began his career as a starting pitcher. However, in his third season he was converted into a relief pitcher. His first year coming out of the bullpen was a massive success and he was named an All-Star. The following season is widely considered to be the greatest single season ever pitched by a closer. In 2003, he tied the record for most saves in a season with 55 and did not blow a single one. He posted a ridiculous 1.20 ERA and won the Cy Young Award. Unfortunately for Gangé, he began to suffer numerous injuries. Multiple surgeries on his pitching arm led to him never coming anywhere close to his one historic season.
4 Randy Jones
Randy Jones had an amazing start to his MLB career. In just his third season, he finished second in the league in Cy Young voting. The following year, he ended up winning the award. He was a lefty who was known for his hard sinker that created a lot of ground balls. In his Cy Young winning year in 1975, he pitched an absolutely ridiculous 315.1 innings. Aside from one decent year in 1978, the rest of his career was mediocre. His ERA constantly fluctuated around 4.00. He is now infamously known as the only Cy Young Award winner to ever finish his career with a losing record.
3 R.A. Dickey
R.A. Dickey may have one of the most interesting careers in the history of baseball. He was a first round draft pick who played a couple of full seasons as a starting pitcher for the Texas Rangers. The beginning of his career was not very successful and he was demoted to the minor leagues. He then decided to develop a knuckleball pitch, but he continued to bounce around the league in the following years and signed minor league deals. It wasn't until he joined the New York Mets that he thrived. He posted terrific numbers all three seasons he played for them and, in his last season with the team at 38 years old, he won the Cy Young Award. He was then traded to the Toronto Blue Jays in exchange for Noah Syndergaard and Travis D'Arnaud in what is now considered a horribly lopsided trade because Dickey has struggled tremendously ever since being traded and Syndergaard is one of the best young pitchers in the MLB.
2 Jim Lonborg
The Boston Red Sox looked like they had a sure Hall of Fame pitcher when Jim Lonborg came up to the big leagues. Standing at 6'5", Lonborg won the Cy Young in 1967 in just his third major league season. That 1967 season is known as the"Impossible Dream" season for the Red Sox because they made it all the way to the World Series with a team that did not have high expectations. In that season, Lonborg led the league in wins, game started, and strikeouts. However, all of those numbers in that magical season would remain his career highs. He enjoyed a long career, but never lived up to the expectations that followed him after the "Impossible Dream" season.
1 Dwight Gooden
There has never been a young pitcher that has been surrounded with as much hype as Dwight Gooden. He was 19 years old when he came up with the New York Mets and in his rookie season struck out 276 batters. His 98 mph fastball and sweeping curveball were nearly impossible to hit, and he earned the nickname "Doctor-K." A section in Shea Stadium was called "The K Korner" because they would post a "K" every time Gooden struck someone out. His second year was somehow even more impressive than his first, and he won the Cy Young Award in 1985 by posting a 1.53 ERA and 268 strikeouts in 276.2 innings pitched. Many consider this to the greatest single season performance by a pitcher in the history of baseball. However, Gooden began to develop drug problems and was arrested multiple times for possession and even fighting with police. The drug-related downfall of Gooden is one of the saddest stories in the history of sports. Even though he was able to have a long career, he was never able to get anywhere close the unreal level he had achieved as a 20 year old Cy Young Award winner.
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