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The best Yankees to never win a championship

As we wrap up our Champions Series, let’s take a look at the names who never got a chance to win a World Series with the Yankees.

New York Yankees v Milwaukee Brewers Photo by Mitchell Layton/Getty Images

This week, we’re in the process of wrapping up our Champions Series profiling the Yankees’ 27 World Series-winning teams. If you’ve read those articles, you’ve seen plenty of familiar names pop up, from the Ruths to the DiMaggios to the Mantles to the Jeters. Even beyond the biggest names, there are many Yankees who played for multiple championship teams.

However, there have been many good Yankees over the years who just didn’t get the chance to play for a championship teams. To make up for their names not coming up during the Champions Series, here are, according to Baseball Reference WAR, the best Yankees who didn’t win a World Series ring with the team.


3. Jack Chesbro (29.8)

Chesbro was the franchise’s first star, playing the first seven years of their existence in New York, back when they were the Highlanders. The spitball specialist peaked in 1904, throwing a presently unimaginable total of 454.2 innings while winning 41 games.

That season also represented Chesbro’s only legitimate chance to win a title in New York, as they weren’t eliminated from the AL pennant race until the final day of the season. Unfortunately for Chesbro, their elimination came in part due to an ill-timed wild pitch from him.

2. Mike Mussina (35.1 WAR)

The Yankees’ signing of Mussina ahead of the 2001 season is one of the best free agent acquisitions in franchise history. Despite the success he had with the team, it never led to any World Series titles.

Mussina had eight good years in New York, playing for two AL pennant-winning teams, and appearing in the playoffs in seven years. In 2001, the future Hall of Famer was not only heartbreakingly close to a perfect game (one strike away), but also to that elusive World Series ring (two outs away). He ended his career by winning 20 games for the first time in 2008, though the Yankees fell short of the postseason. Like another person who will be appearing on this list, Mussina’s time in New York is bookended by years that are right after/before a title team.

Mussina did go on to find championship success as a high school basketball coach in Pennsylvania.

1. Mel Stottlemyre (43.1 WAR)

During Stottlemyre’s rookie season, the Yankees lost in seven games in the World Series. It was the franchise’s fifth consecutive Fall Classic appearance and ninth in 10 years. It would’ve been hard to imagine that the next couple years wouldn’t play out in a similar manner. Unfortunately, due to a number of factors, including the disastrous CBS ownership, Stottlemyre wouldn’t ever return to the postseason.

That drought had nothing to do with the pitcher himself, who was the Yankees’ ace on those disappointing teams. He made five All-Star teams and had a career sub-3.00 ERA, but retired in 1974, two years before the Yankees’ returned to the World Series. Thankfully, he did later go on to earn plenty of rings and adulation as the pitching coach of the late-‘90s/early-‘00s Yankees’ dynasty.


3. Rickey Henderson (30.8 WAR)

Rickey may have only spent 4.5 seasons in New York, but, individually, what a handful of seasons they were.

In his first year with the Yankees, Henderson put up 28 home runs, 80 stolen bases, a 157 OPS+ and finished third in MVP voting. Other than 1987, he would lead the league in stolen bases every full season he was in New York. He actually set the franchise record for steals with 326 until Derek Jeter broke it (in far more games than Rickey).

However, with Rickey’s Rickey-ness and George Steinbrenner probably at the height of his George Steinbrenner-ness, things did not work out and in 1989, Henderson was traded back to the A’s without appearing in a single playoff game for New York. It’s unlikely that he regretted the second trade, either, as Henderson finally won his first championship with the A’s that very season.

2. Roger Peckinpaugh (32.1 WAR)

Acquired in 1913, near the nadir of franchise history, Peckinpaugh was there as things started to turn around, with the addition of Babe Ruth and others. Known for his excellent defense, he was one of the Yankees’ best players over his tenure, and served as captain from 1914-21. He also had the reputation as an excellent leader, so much so that it may have played a part in his exit.

After a loss in the 1921 World Series, Ruth reportedly complained to the front office about the managerial style of Miller Huggins and advocated for Peckinpaugh (who had served as an interim manager for the team in 1914) to replace him. The Yankees’ brass decided to nip that in the bud and traded the shortstop to the Washington Senators ahead of the 1922 season. Peckinpaugh would win the 1924 World Series with the Senators, but missed out on being a part of the Yankees’ title teams and the “Murderers’ Row” 1927 squad.

1. Don Mattingly (42.4 WAR)

Who else would it be?

Mattingly is one of if not the most beloved Yankee for those who watched him play, winning an MVP and being a six-time All-Star in the ‘80s and early ‘90s. His six-year stretch from 1984-89 would rival the peaks of a lot of legends. Unfortunately, as the calendar turned into the new decade of the 90s, back problems began to flare up more and more. He had one playoff hurrah with his home run in the 1995 ALDS, but that series would be the only postseason appearance of his career.

Unfortunately, Donnie Baseball’s career just happened to fall right exactly in the Yankees’ longest drought without a World Series appearance. With his debut coming in 1982 and final season in ‘95, he missed out on a Fall Classic trip by just one season on both ends. He’s made it back to the playoffs 10 times as a coach or manager, but is still seeking that first title.