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Come Fan with UsWednesday, June 24, 2026

In search of the saddest Yankee

Who were the best players to star for the Yankees without winning a championship? Here’s a position-by-position list.

Rick Scuteri-USA TODAY Sports

Last week, our own Justin Bopp created this image:

Mattingly_medium

It’s funny because of the face. But unpack it a little. What do you remember Gollum for? His doomed quest for a ring. What is Don Mattingly’s legacy as a player? One of the few Yankees who never got that ring. Now unpack it even more.

Wait, no, that’s it. Gollum and Mattingly and rings. That analogy is good for a chuckle, maybe, on a slow day. But it got the idea gland pumping: Is Don Mattingly the saddest Yankee? As in, is there anyone else in Yankees history who can combine a comparable good-to-great Yankees career without ever winning a championship?

Rules:

  1. This is about the players who never won a championship at all. Rickey Henderson had a brilliant Yankees career, and Rickey didn’t win a title with them, but Rickey did win a championship. Don’t worry about Rickey.I wanted to find players who played with the Yankees long enough to make an impact, or at least be (mostly) remembered as Yankees. Jack McDowell was a talented pitcher who was never on a championship team, and he played a season with the Yankees. He doesn’t count.

Considering that last point, the quick, dirty, and effective way to search for the saddest Yankee is to search only for Wins Above Replacement accrued as a Yankee, then sift through that list for the players who didn’t win a World Series. So here you go, the all-time team of Yankees who didn’t win a World Series, despite being associated with the Yankees for an extended period:

C - Butch Wynegar, 11 WAR as a Yankee, 1982-1986
1B - Don Mattingly, 42 WAR, 1982-1995
2B - Horace Clarke, 16 WAR, 1965-1974
3B - Jerry Kenney, 9 WAR, 1967-1972
SS - John Knight, 6 WAR, 1909-1911, 1913
LF - Birdie Cree, 15 WAR, 1908-1915
CF - Bobby Murcer, 28 WAR, 1965-1974, 1979-1983
RF - Jesse Barfield, 10 WAR, 1989-1992
DH - Danny Tartabull, 8 WAR, 1992-1995

P - Mel Stottlemyre, 41 WAR, 1964-1974
P - Mike Mussina, 35 WAR, 2001-2008
P - Russ Ford, 26 WAR, 1909-1913
P - Tommy John, 20 WAR, 1979-1982, 1986-1989
P - Fritz Peterson, 20 WAR, 1966-1974

CL - Dave Righetti, 224 saves, 1979-1990

Some notes on the search for the saddest Yankee:

  • Hold on, there, Kid Elberfeld fans. The modern World Series started in 1907, and most of Elberfeld's seasons with the Yankees came before that. Wouldn't be fair to include him.

  • Clarke had to be here, having given his name to the whole Yankees era of not-winning things that -- fairly or not -- pretty much coincided exactly with his career.

  • Jesse Barfield gets bonus points for missing out on the Blue Jays' titles, too, though that doesn't make him a strong contender

  • Mel Stottlemyre won as a pitching coach, but otherwise, he is almost identical to Mattingly in tenure and value

  • Someone is going to use this information as an argument against Mike Mussina, so do us a favor and eat this article after reading it. Quickly, there's no time, hurry, eat the article, leave no evidence, eat it.

  • Mike_mussina_redux_medium Mike Mussina, 2006. (Getty Images)

  • Bobby Murcer was so danged good in his 20s. He also played for the Yankees on two separate occasions, rejoining the team after their '78 title. He played in one World Series and went 0-for-3. Oof.

  • I'd never heard of Jerry Kenney, but apparently, he was a golden defensive god in his limited time. I had Home Run Baker at first because I missed his titles with the A's. Once a year, I note that Omar Vizquel hit more home runs in a single season than Home Run Baker ever did. This is that time.

  • Russ Ford didn't pitch for long, but boy, he was good when he pitched. If only there were some kind of surgery back then. Maybe something named after ...

  • Tommy John pitched for the Dodgers in the '70s, the moved to the Yankees for two separate tours. Do you know how hard it is to have a career with the Dodgers and Yankees and not have a ring?

  • Oh, right, Don Mattingly.

There is more competition than I expected for the crown of saddest Yankee. Stottlemyre was the Mattingly of pitching, give or take; only his titles as a coach separates them. John and Murcer managed to mix in two different stretches with the Yankees, and they still didn’t win a World Series with anyone.

No, it’s Mattingly. He missed ‘78 by four seasons, and he missed ‘96 by one. It’s hard to throw 14 darts at a list of Yankees seasons and miss a championship. Somehow, he managed. All he has are the fantastic memories of a spectacular career, a lucrative second career as a manager, and being better at baseball than any of us will ever be at anything in our lives.

Don Mattingly is the saddest Yankee.

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(Photo by Lisa Blumenfeld/Getty Images)

Take it easy on him, Joe. He did his best. It was Bobby Meacham’s fault.

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