The New York Yankees have many top pitchers in their history and they proved their worth with season-winning performances. However, many of them missed the Cy Young Award, the top pitching honor, despite getting frequent nominations.

Jimmy Key came up second in 1994

Jimmy Key had a career spanning 15 years, largely divided between his time with the Toronto Blue Jays and the New York Yankees. He donned the mantle of the staff ace for both teams at different junctures. In 1987, he distinguished himself by leading the American League in ERA with an exceptional 2.76 and WHIP at 1.06. During that season, he secured the runner-up position in the Cy Young Award race, narrowly trailing Roger Clemens. In the strike-shortened 1994 season, his second year with the Yankees, Key recorded an impressive 17-4 record with a 3.27 ERA over 25 starts. This performance earned him a second-place finish in the Cy Young Award Voting, with David Cone taking the top honor.

Yankees’ David Wells was voted third in 1998 and 2000

David Wells, a robust left-handed pitcher, embarked on his career as a reliever and swingman, contributing significantly to the illustrious Toronto Blue Jays squads from the early 1990s. Over time, he solidified his role as a permanent member of the starting rotation and achieved legendary status by hurling a perfect game while wearing the New York Yankees uniform.

His remarkable seasons in 1998, where he posted an 18-4 record with a 3.49 ERA, a stellar 1.05 WHIP, and 214.1 innings pitched, and in 2000, when the Yankees starter notched a 20-8 record with a 4.11 ERA, a 1.29 WHIP, and 229.2 innings pitched, both garnered him third-place finishes in the American League award voting. His consistency extended well into his mid-40s, demonstrating his enduring prowess on the mound.

Andy Pettitte missed the first slot in 1996

A fixture in the postseason at the zenith of the New York Yankees’ dynasty, Andy Pettitte delivered standout performances in October, amassing a notable 19-11 record with a 3.81 ERA across 276.2 career playoff innings. His highest finish in Cy Young Award voting came in 1996, a year when the iconic Yankees core clinched their inaugural championship. During that season, the southpaw compiled an impressive 21-8 record with a 3.87 ERA over 221 innings in just his sophomore year in the majors. His exceptional efforts earned him 11 out of 28 first-place votes but narrowly saw him fall short in a closely contested race, with Pat Hentgen emerging as the victor.

Mike Mussina ended up second in 1999

Mike Mussina‘s illustrious 18-year career saw him secure impressive placements in the AL Cy Young Award voting, landing in the top six on nine separate occasions. However, his sole appearance in the top three occurred in the 1999 season, which is somewhat surprising given his remarkable achievements throughout his career.

Curiously, 1999 wasn’t his most outstanding individual season statistically. That year, the Yankees pitcher accumulated his 12th highest single-season WAR (4.4) while achieving an 18-7 record with a 3.50 ERA, 1.27 WHIP, and 172 strikeouts across 203.1 innings.

Arguably, his peak came in the 1992 campaign, his first full season in the majors, when he boasted a remarkable 2.54 ERA over 241 innings and a stellar 8.2 WAR. Despite this incredible performance, the Yankees pitcher only managed to secure a fourth-place finish in the Cy Young voting, with Dennis Eckersley, Jack McDowell, and Roger Clemens ahead of him in the rankings.

Mariano Rivera fell short of winning Cy Young five times

Mariano Rivera‘s illustrious Hall of Fame career didn’t result in a Cy Young Award victory, but the Yankees closer managed to secure top-five finishes in the voting an impressive five times.

In 1996, Mariano Rivera achieved a remarkable tally of 130 strikeouts over 107.2 innings. His pivotal role significantly contributed to the Yankees’ triumphant quest for the World Series championship. Despite registering only eight wins and five saves, Rivera’s exceptional performance secured him a remarkable third-place finish in the 1996 American League Cy Young Award balloting. Closing out the 1999 season, the Yankees closer orchestrated a spectacular feat, weaving together an astonishing streak of 43 consecutive scoreless innings spanning both the regular season and postseason, earning him a well-deserved third-place slot in the AL Cy Young Award voting.

Fast-forwarding to the 2004 season, Rivera’s performance showcased a remarkable 1.94 ERA and a career-high 53 saves out of 57 opportunities, marking his third time leading the major leagues in saves. Alongside claiming his third AL Rolaids Relief Man Award, the Yankees closer once again secured a third-place finish in the AL Cy Young Award voting. In 2005, Rivera continued to dazzle, amassing 43 saves in 47 opportunities but he found himself narrowly trailing starting pitcher Bartolo Colon, earning the runner-up position for the AL Cy Young Award.

Rivera’s 2008 season etched itself as one of his most remarkable individual years. With a stellar 1.40 ERA, he clinched 39 saves out of 40 opportunities and maintained an impressive average of 9.81 strikeouts per 9 innings pitched. These extraordinary achievements propelled him to a commendable fifth-place finish in the AL Cy Young Award balloting.

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