Pitchers With the Most Cy Young Awards

Receiving a Cy Young Award is a sign of true triumph in the pitching community. Only 21 pitchers have ever received this honor, and Roger Clemens has won it more than anyone else.

There are 4 pitchers below, all of whom have shown themselves to be Cy Young Award magnetics - earning the title time and time again.

What Is a Cy Young Award?

This award is a prize given out every year. It’s handed to the best pitchers in the National League and the American League. Each league gets one winner, but only 21 people have been chosen since it began.

The award was first introduced in 1956, after the well-loved and outstanding pitcher Cy Young died in 1955.

Cy Young was a Hall of Fame pitcher, and after his death, it became clear that his immense skill wasn’t appreciated as much as it should have been. There were no rewards dedicated to just pitchers, so this one was created in his honor.

Originally, just one pitcher from Major League Baseball was able to win the trophy, but in 1967 the rules changed to allow both AL and NL to take home an award. You can often predict who will win based on the World Series Odds.

Members of the Baseball Writers Association of America vote on who will win the award each year. The player with the most votes is given the Cy Young prize.

The first ever winner was Don Newcombe who played for the Dodgers, he took his award in 1956. The first player to win via a unanimous vote was Sandy Koufax in 1963. He was also the first to win the award twice.

Pitchers With the Most Cy Young Awards

Now onto the pitchers who have won the Cy Young Award the most. Each of these players were fantastic, both in their time and based on current standards. And of course, Roger Clemens is in the lead.

Roger Clemens - 7 Cy Young Awards

Clemens has won the Cy Young Awards 7 times. His lead in this competition is leagues above everyone else. You cannot even suggest that Clemens’ talent is due to a team effort either, as this pitcher won his awards while on different teams and in different leagues.

Clemens’ first win was in 1986 when he played with the Boston Red Sox (American League). In that season, the legend won the American League Most Valuable Player award too. This makes him just one of 11 pitchers to take home both achievements in one season.

His other awards were in 1987 and 1991 with the Red Sox, 1997 and 1998 with the Toronto Blue Jays, 2001 with the New York Yankees, and lastly in 2004 when Clemens switched to the National League with the Houston Astros.

The switch meant that Clemens was one of just 5 Cy Young Award winners to earn the trophy in the American League and the National League.

Randy Johnson - 5 Cy Young Awards

Johnson is the second pitcher to have won the Cy Young Award 4 times in a row. He did this between 1999 and 2002 when the National League player was part of the Arizona Diamondbacks.

Johnson was the most dominant player of his time and even managed to pitch no-hitters in both the National League and the American League.

His first ever Cy Young Award was in 1995 when Johnson was playing in the American League with the Seattle Mariners.

Greg Maddux - 4 Cy Young Awards

Maddux is the first pitcher to complete the quadruple Cy Young win, but unlike Johnson, he wasn’t able to grab a 5th. Maddux’s 4 wins were between 1992 and 1995, while he played for the National League’s Atlanta Braves.

During that same epic 4 years, Maddux also won the MLB wins leader 3 times, became the World Series Champion, and won the MLB ERA Leader 3 times.

This early 90s era was the height of Maddux’s career.

Steve Carlton - 4 Cy Young Awards

Carlton, like Maddux, achieved all of his Cy Young awards while playing for one team. This time the legendary pitching was within the National League’s Philadelphia Phillies.

Carlton stayed with the Phillies between 1972 and 1986. This was his longest time with just one team, sticking with Philadelphia for 14 years.

Of those 14 years, 4 of them were graced with Cy Young Awards in 1972, 1977, 1980, and 1982.

In that same time period, Carlton won the Triple Crown, the Gold Glove Award, the World Series, the NL ERA Leader, and the NL Strikeout leader.

Carlton’s era with the Philadelphia Phillies was his strongest, having only received 3 career highlights before the move and none after.

For everything that Carlton achieved, the Philadelphia Phillies retired his number 32 and entered him into their Hall of Fame.

Summary

Receiving the Cy Young Award is one of the highest honors a pitcher can get. And receiving it more than once is even more outstanding. These 4 pitchers were legends in their day, and their name still holds weight to this day.

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