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All-Time Red Sox vs. All-Time Yankees: The Pitchers

How do the best pitchers stack up vs those from the Yankees?

Boston Red Sox v. New York Yankees

For this comparison exercise I used the best single years of both the Red Sox players on my All-Time roster and those of the Yankees All-Time roster I created with the help of our friends at Pinstripe Alley. I didn’t always select just the highest WAR season, and often awards like Cy Young or MVP factored into the selection if the years were close statistically. We are looking at who would win a single series here, not what they did over their entire careers, so these individual years are weighted more than total career performance for this exercise. I have provided tables with most of the relevant information that went into my decision making. As has been the case with this whole exercise, these are my opinions based off of data. This is not scientific or crowd sourced.

Red Sox Pitchers

Position Player Name Throws Year FanGraphs WAR/ERA- Slash Line Career WAR (w/TM)
Position Player Name Throws Year FanGraphs WAR/ERA- Slash Line Career WAR (w/TM)
SP1 Pedro Martinez R 1999 11.6 WAR , 42 ERA- 23 W, 2.07 ERA, 313 SO 51.9
SP2 Roger Clemens R 1986 7.1 WAR, 57 ERA- 24 W , 2.48 ERA, 238 SO 76.8
SP3 Cy Young R 1901 7.8 WAR, 44 ERA- 33 W, 1.62 ERA, 158 SO 54.8
SP4 Lefty Grove L 1935 7.2 WAR, 59 ERA- 20 W, 2.70 ERA, 121 SO 34.6
SP5 Luis Tiant R 1974 6.1 WAR, 76 ERA- 22 W, 2.92 ERA, 176 SO 28.9
CL Koji Uehara R 2013 3.1 WAR, 26 ERA- 1.09 ERA, 0.57 WHIP, 101 SO 6.1
RP2 Jonathan Papelbon R 2006 3.1 WAR, 20 ERA- 0.92 ERA, 0.78 WHIP, 75 SO 14.1
RP3 Craig Kimbrel R 2017 3.2 WAR, 31 ERA- 1.43 ERA, 0.68 WHIP, 126 SO 5.8
RP4 Smokey Joe Wood R 1912 7.6 WAR, 58 ERA- 1.91 ERA, 1.01 WHIP, 258 SO 26.2
RP5 Chris Sale L 2017 7.6 WAR, 63 ERA- 2.90 ERA, 0.97 WHIP, 308 SO 17.4
RP6 Curt Schilling R 2004 6.5 WAR, 69 ERA- 3.26 ERA, 1.06 WHIP, 203 SO 15.1
RP7 Dick Radatz R 1964 2.9 WAR, 60 ERA- 2.29 ERA, 1.03 WHIP, 181 SO 10.1
73.8 341.8

Yankee Pitchers

Position Player Name Throws Year FanGraphs WAR/ERA- Slash Line Career WAR (w/TM)
Position Player Name Throws Year FanGraphs WAR/ERA- Slash Line Career WAR (w/TM)
SP1 Ron Guidry L 1978 9.1 WAR, 47 ERA- 25 W, 1.74 ERA, 248 SO 49.3
SP2 Whitey Ford L 1956 5.0 WAR, 62 ERA- 19 W, 2.47 ERA, 141 SO 54.9
SP3 Andy Pettitte L 1997 7.7 WAR, 65 ERA- 18 W, 2.88 ERA, 166 SO 57.1
SP4 Lefty Gomez L 1934 4.8 WAR, 56 ERA- 26 W, 2.33 ERA, 158 SO 34.7
SP5 C.C. Sabathia L 2011 5.8 WAR, 71 ERA- 19 W, 3.00 ERA, 230 SO 31.6
CL Mariano Rivera R 2005 2.9 WAR, 32 ERA- 1.38 ERA, 0.87 WHIP, 80 SO 39.1
RP2 Rich Gossage R 1978 2.4 WAR, 55 ERA- 2.01 ERA, 1.09 WHIP, 122 SO 15.0
RP3 Dave Righetti L 1986 3.0 WAR, 60 ERA- 2.45 ERA, 1.15 WHIP, 83 SO 23.7
RP4 Sparky Lyle L 1977 2.5 WAR, 55 ERA- 2.17 ERA, 1.20 WHIP, 68 SO 10.9
RP5 Aroldis Chapman L 2019 2.1 WAR, 48 ERA- 2.21 ERA, 1.11 WHIP, 85 SO 6.8
RP6 Dellin Betances R 2014 3.0 WAR, 36 ERA- 1.40 ERA, 0.78 WHIP, 135 SO 11.3
RP7 David Robertson R 2011 2.3 WAR, 26 ERA- 1.08 ERA, 1.13 WHIP, 100 SO 10.9
50.6 345.3

No. 1 Starting Pitcher: 1999 Pedro Martínez vs 1978 Ron Guidry

The Yankees have been a franchise rich in position players with immense star power, but their pitching has always been just good enough. Ron Guidry bucked this trend by putting up the greatest season in Yankees history by a starting pitcher. But guess what? It’s not even close to 1999 Pedro Martínez. I’m on record saying that I think his 1999 is the greatest single pitching season of all time. You could argue his 2000 season was better, but nonetheless this means Guidry is at a disadvantage. In this battle of Cy Young winners it’s Martínez who gets the nod.

Edge: Pedro Martinez (BOS)

No. 2 Starting Pitcher: 1986 Roger Clemens vs 1956 Whitey Ford

In 1986, a 23-year-old Clemens won the Cy Young and the MVP Awards in the same season. He also won 24 games while striking out 238 batters. Whitey Ford was excellent in this season, helping to lead the Yankees to yet another World Series victory, but his numbers don’t quite stack up to those of Clemens. For their respective careers it becomes even less close as Clemens has seven Cy Young awards, three of which were won with the Red Sox, to Ford’s one.

Edge: Roger Clemens (BOS)

No. 3 Starting Pitcher: 1901 Cy Young vs 1997 Andy Pettitte

The surface numbers tell a very different story than the advanced metrics in this head-to-head matchup. Young has a massive advantage of 33 wins to Pettitte’s 18. Young’s ERA was just 1.62, over a run lower than Pettitte’s 2.88 ERA. However FanGraphs WAR has it 7.8 WAR for the former and 7.7 WAR for the latter. When we adjust for park factors and run scoring environment, ERA- gives a strong edge of 44 vs 65 in favor of Young. I have to agree.

Edge: Cy Young (BOS)

No. 4 Starting Pitcher: 1935 Lefty Grove vs 1934 Lefty Gomez

I certainly wasn’t expecting a battle of two left-handed starters, both of whom are unimaginatively nicknamed Lefty, let alone the fact that they each had their best seasons for rival clubs just a year apart. You can’t make this stuff up. In his overall career, Grove blows Gomez out of the water. For this individual season, however, it’s a bit closer. FanGraphs WAR gives Grove a 2.4 WAR advantage while Baseball-Reference has him ahead by just one win. Gomez was 25 during his spectacular season while Grove was in the twilight of his career at 35 years old. ERA- gives a slight advantage to Gomez as does ERA+, but in each example it’s by a much slimmer margin than the gap in WAR. I give the slight edge here to Grove.

Slight Edge: Lefty Grove (BOS)

No. 5 Starting Pitcher: 1974 Luis Tiant vs 2011 C.C. Sabathia

C.C. Sabathia helped the Yankees win a World Series in 2009, something that, despite his herculean efforts to do so in 1975, Tiant was unable to accomplish. Both FanGraphs WAR and Baseball Reference WAR say that Tiant had the better season. For their careers, Baseball-Reference likes Tiant by a small degree while FanGraphs likes Sabathia by a larger degree. During these respective seasons, each pitcher finished fourth in the Cy Young voting, while Tiant finished slightly higher in MVP vote. The tie breaker has to go to what they each did in the playoffs and Tiant pitched 34 innings to a 2.65 ERA, Sabathia threw just 8 ⅔ innings to a 6.23 ERA. Give me El Tiante.

Slight Edge: Luis Tiant (BOS)


These two units are incredible. The Red Sox have three insanely good closers at the back end including the three lowest seasons according to ERA-, but the Yankees have Mariano Rivera. I ended up putting three players who had their best years as starters in the Red Sox bullpen in Chris Sale, Curt Schilling, and Smoky Joe Wood. This speaks to the Red Sox incredible depth at starting pitcher. The Yankees have historically had excellent bullpens and retained their good bullpen arms for long stretches of their careers. I’m going to give the Yankees the edge here even though the Red Sox have a very good argument in their favor.

Slight Edge: NYY

Final Tally (P): BOS 5, NYY 1

Final Tally (Total): BOS 9, NYY 7

Final Assessment: Edge-Red Sox

If you sum up the total FanGraphs war of the lineup, the bench, the starting rotation, and the bullpen in their best seasons it comes out to 182.4 for the Red Sox and 161.3 for the Yankees. The major advantage is in the area of starting pitching, where the Red Sox dominate. This isn’t quite playing fair because some exceptions were made. Mantle at DH is one example and three Red Sox starters in the bullpen is another. If you remove the WAR contributions of Sale, Schilling, and Wood the number is 160.7 for the Red Sox, less than a win below the Yankees mark. I would strongly argue that even if we reduced their workloads for reliever expectations they would post strong totals giving the Red Sox the overall advantage.

Offensively the Yankees had six advantages on offense, while I only gave the Red Sox Garciaparra, Williams, and Betts. However, only Mantle, DiMaggio, and Rodriguez were substantial advantages. The Red Sox bench is also a large advantage and allows for excellent lineups against both righties and lefties. The Yankees are heavily left handed and could benefit from a bit more balance. The pitching carries the Red Sox and I think that decides it for me. In a series, I’m taking this Red Sox team at its best over the Yankees.

This finally wraps up my All-Time Red Sox roster series, I hope you’ve all enjoyed reading it as much as I enjoyed writing it. If you missed any, you can find the links to all of the entries below.

Introduction and Honorable Mentions Part One

Honorable Mentions Part Two

Bench: Bobby Doerr

Bench: Jason Varitek

Bench: Manny Ramirez

Bench: Tris Speaker

Bench: Carl Yastrzemski

Starting Catcher: Carlton Fisk

Starting First Baseman: Jimmie Foxx

Starting Second Baseman: Dustin Pedroia

Starting Third Baseman: Wade Boggs

Starting Shortstop: Nomar Garciaparra

Starting Left Fielder: Ted Williams

Starting Center Fielder: Fred Lynn

Starting Right Field: Mookie Betts

Starting Designated Hitter: David Ortiz

Reliever: Dick Radatz

Reliever: Curt Schilling

Reliever: Chris Sale

Reliever: Smoky Joe Wood

Reliever: Craig Kimbrel

Reliever: Jonathan Papelbon

Reliever: Koji Uehara

Starter: Luis Tiant

Starter: Lefty Grove

Starter: Cy Young

Starter: Roger Clemens

Starter: Pedro Martínez

Constructing the Lineup

Red Sox/Yankees Hitters