The Tuesday Discussion: The Greatest, Without A Ring

January 6, 2026

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This week we presented the following to our writers:

Outside of Aaron Judge (there is still hope!) who was the greatest Yankee (of more than 5 years) to never win a World Championship?

Here are their responses:

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Cary Greene - Based on time served with the Yankees, the answer would have to be Don Mattingly, a team captain whose entire 14-year career (1982-1995) spanned the Yankees' championship drought, missing the 1996 title by a year. Mattingly spent his entire career as a Yankee. Does that make him the greatest Yankee to ever not win a championship? Perhaps. Mattingly certainly has more personal accolades, with his MVP award, his Player of the Year award, his nine Gold Gloves and three Silver Slugger awards and that he was a six-time All-Star. 

Mattingly is certainly a greater Yankee than two of the three runners up, such as Mel Stottlemyre or Bobby Murcer and there's really no debating this. However, Mike Mussina, at least to me, wins the title of Greatest Yankee Never to Win a Title over Mattingly and it's really not close. 

Not only did Moose make the Hall of Fame, but he sustained his excellence for longer than Mattingly did and it shows in the most telling stat of all -- bWAR. Moose has a career 82.8 bWAR, which almost doubles Mattingly's 42.4. Moose also won six Gold Gloves and made 5 All-Star appearances. Moose was clearly the more valuable player over the course of his career, even though he only played for the Yankees for eight seasons. 

On one hand, we have a player who played for 14-years all as a Yankee (Mattingly) and we have a player who played for 18-years total, but only for eight seasons as a Yankees. Based on the way the question is worded, since both players played for the Yankees for at least five seasons, the greater of the two players isn't really even debatable -- it's very easily Mussina and that's why he's in the Hall of Fame and Mattingly isn't. Simple as that!

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Paul Semendinger - My heart sides with Don Mattingly on this. I also think Mel Stottlemyre has a claim here. But, a Hall of Famer that many forget is Dave Winfield.

For his first 8 seasons in the Bronx, Winfield averaged .291/25/102 while playing all three outfield positions exceptionally well, with a rocket arm.

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Tim Kabel - I would have to say that after Aaron Judge, the two greatest Yankees to have never won a World Series would be Don Mattingly and Mike Mussina. 

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Ed Botti - In my opinion, it is Don Mattingly.

During his prime years he was an absolute terror to the rest of the AL. Unfortunately for Don, he played in an era when George Steinbrenner did his best to trade away valuable assets for older has beens, fired managers almost every season, pitching coaches and just about anyone else he could blame something on, and Don never got a chance at the ring.

The 1985 and 1987 Teams were close, and of course 1994 was the team that could have won it all, had greed not reared its ugly head and ruined the season.

His era was marked by average starters and constant turmoil and chaos.

It’s interesting how things turn out. Today, many  are wishing for Hal to be more like George Steinbrenner because Hal is….. well Hal.

But back in the Mattingly, Henderson,  Winfield era, George was despised by most (me included) and was a big part of why Mattingly, Henderson,  Winfield never won a world championship together.

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Derek McAdam - Don Mattingly is the first name that comes to mind. It’s extremely unfortunate for Don that he played in such a down-era for Yankee baseball. If only he could have stuck around for one more season, he could have won a ring with the Yankees. Hopefully, he can win one as a coach before he calls it a career. 

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Mike Whiteman - Don Mattingly of course is the one we think about the most in response to this question, but there were others...

Roger Peckinpaugh - the Yankee shortstop who gets no love. Averaged almost four WAR per season from 1914-1921. Best season was 1919 when he had a 125 OPS+ and 6.3 WAR. 

Bobby Murcer - Four-time All Star, a favorite player to many growing up in the 1970s. 

Mike Mussina - Hall of Famer came out on the short side of both World Series (2001 and 2003). Like Mattingly, the Yankees won the World Series the year after he retired (2009). 

Dave Winfield - An All-Star each of his eight full seasons in Pinstripes. Infamously had one hit in 22 at bats (.045) in the 1981 World Series. Later found redemption and his ring in 1992 with Toronto. 

Mel Stottlymyre - Started three games in the 1964 Series against St. Louis as a rookie. Never came close to postseason again. 

In the end, I go with Mattingly. 

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