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The Tuesday Discussion: Outside of The Babe, Who Was The Best Yankee/Red Sox?

June 29, 2021


This week’s Tuesday Discussion Question comes from new writer Timothy Kabel:

In the spirit of last weekend’s series, who do you believe was the greatest player to have been on both the Yankees and the Red Sox other than Babe Ruth, of course?


Lincoln Mitchell – This is a fantastic question because it made me think about the whole of baseball history and to remember who had played where. However, the answer to the question is pretty clear. Other than the Sultan of Swat, the best player to play for both the Red Sox and the Yankees was Rickey Henderson. Henderson is one of my all time favorite players. I saw him play quite a bit in 1980, his first full year in the big leagues because I was living in San Francisco and he was playing across the bay with the A’s. For that one year, and probably a few more, he was the most exciting player I ever saw. I particularly like this question because Henderson was much better as a Yankee than he was with Boston.


Paul Semendinger – An interesting question. In order, the following were the names I first thought of:

Sparky Lyle

Elston Howard

Wade Boggs

Roger Clemens

Ethan then starting to use Baseball-Reference and shared names and we talked baseball…

The best player, hands-down, for a career, was Rickey Henderson. That’s a given to me.

But, there are so many other greats – Red Ruffing, Waite Hoyt, Herb Pennock, and then all those stars from the Red Sox who went on to help the Yankees win their first pennants: Everett Scott, Carl Mays, Wally Schang, Del Pratt, Joe Dugan…

I just remembered as I wrote this that David Cone and David Wells both pitched for the Sox…

(Such a fun topic to ponder…)

Best Player Period – Rickey Henderson

The player who was the best Yankee and Red Sox (a great player for both team) was Wade Boogs.

The pitcher who was great for both teams was Roger Clemens.

My favorite player from the list – Ol’ Sparky…


Ed Botti – Great question, I am going to answer that from the perspective of a player on both teams that made the biggest impact on the Yankees.

Over the years there have been several players that have played for both teams. Some came via free agency and some came via a rare trade.

Some trades were fair trades such as the Mike Easler for Don Baylor trade of 1986. Baylor ended up hitting 31 home runs helping to lead the Red Sox to the 1986 World Series, while Easler hit .302 with 14 home runs in the Bronx.

Some free agents worked out very well.

Johnny Damon was a key player in the last World Series winning team in 2009.

Wade Boggs had some great seasons in pinstripes and was a big piece of the 1996 World Series Champions.

Who can deny the impact Roger Clemens had in the Bronx by going 70-42 in 5 + seasons after coming over in a trade from Toronto?

There have been some duds along the way such as Kevin Youkilis and of course Jacoby Ellsbury.

There have been some so so moves such as Luis Tiant in 1978-1979.

And then there was the one sided trade of Sparky Lyle to the Yankees for Danny Cater and Mario Guerrero in spring of 1972.

Lyle would become an elite closer and contribute mightily in the back to back 1977-78 World Series Championships. Sparky, a lefty would win the Cy Young in 1977 saving 26 games with a 2.17 ERA and throwing 137 innings out of the bullpen. His slider was legendary. Overall he saved 238 games, and pitched sensational in many non-save critical innings as a Yankee.

He is credited with teaching Ron Guidry the Slider, along with bullpen mate Dick Tidrow.

Later he would pen the famous book, The Bronx Zoo with Peter Golenbock.

When the Yankees moved on from him after the 1978 season in favor of a 7 year younger Goose Gossage, he was part of a package that landed Dave Righetti.

So in my book, after Babe Ruth, I’d go with Sparky Lyle.

Today, I wish they could hand him the ball in the 9th inning every night. If you didn’t see him pitch, you missed a masterful pitcher.


Tim Kabel – When I look at the men who played for both the Yankees and the Red Sox, it would be easy to select Roger Clemens or Wade Boggs as the best player other than Babe Ruth to have played for both franchises. However, I’m going to go in a different direction and select someone whom I feel is greatly underrated. Luis Tiant. When you look at his numbers, they were every bit as good as Catfish Hunter’s. Yet, Catfish is in the Hall of Fame and Luis is not. Think about the 1975 World Series. Luis Tiant had complete game victories in games 1 and 4. Game 1 was a shutout. I believe he threw 156 pitches in game 1 and 163 in game 4. He also started game 6 and lasted into the seventh inning. He won 20 games four times in his career. When you add in that windup and the cigars, El Tiante is my choice.


Patrick Gunn – I’m going with Ricky Henderson. Yes, Ricky played for Boston in 2002, his second to last season in the bigs. No, the Red Sox did not see Henderson in his prime, but this question is asking about the best players to have played for both teams aside from Ruth. Henderson not only stands alone amongst the stolen base leaderboard but he also had great power for a speedster and got on-base at a .401 clip with 2,190 career walks.


Mike Whiteman – I don’t know if he was necessarily the best player to have worn both Yankee and Red Sox uniforms, but I think Red Ruffing was one of the more interesting ones.

He began his career in Boston and was 39-93, 4.57 for some bad Red Sox teams. He had two seasons in which he was a 20-game loser. In 1930 he lost his first three starts and was dealt to the Yanks for career reserve outfielder Cedric Durst and cash. Durst batted .245 over 102 games in Boston over the rest of the 1930 season and never played in the majors again.

Upon donning the pinstripes, Ruffing was a changed man. He won his first six decisions and went 15-5 the rest of 1930. He became a Yankee ace throughout the 1930s, winning 175 games over the decade, including four 20-win seasons. He arguably saved his best for the World Series, where he was 7-2, 2.63 for his career.

Ruffing was inducted into the Hall of Fame in 1967.


Ethan Semendinger – There is really only one correct (non-Babe Ruth) answer for this question in Rickey Henderson. However, I also wanted to highlight some other fun names:

Roger Clemens – 7 time Cy Young Award Winner & Should be in the Hall of Fame

Wade Boggs – Hall of Famer & Member of the 3,000 Hit Club

Jack Chesbro – Hall of Famer & Winner of 55 games for the Yankees in 1904

Red Ruffing, Herb Pennock, Waite Hoyt – 3 Hall of Fame Pitchers who are slightly forgotten by Yankees fans. (Also 3 names who would get an honorary retired number from me.)


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