Tuesday, March 3, 2026

How Did The Winningest Pitchers of All Time Do On Baseball's Biggest Stage? Part 4: The Modern Era

 

Roger Clemens

Boston Red Sox 1986, 1988, 1990, 1995

2 Wins, 2 Losses Division series 0-0 World Series

New York Yankees 1999-2003

Division Series 2-4

LCS 2-1

World Series  3-0

Houston Astros 2004-2005

Division Series 2-1

LCS 2-1

 

Yes I'm well aware of the asterisk that hangs over Clemens more than any other pitcher on this list. So let's deal with him before and after.

During his tenure with the Red Sox when he was one of the greatest pitchers whoever lived he was not enough to get them over the hump. In 1986 he did well in the LCS but he couldn't manage a World Series victory and famous in Game 6 he was taken out in the seventh with a blister on his finger. Still you can't blame him for everything that happened in the 10th. The other three occasions the Red Sox were swept by the A's and in 1995 they couldn't get past Cleveland.

His track record with the Yankees is something of a mixed bag. In the five division series in four of them they managed to get the LCS despite Clemens more than anything else. It helps to have a rotation with David Wells and Andy Petite in it. He did better overall in the LCS to be sure and of course he did help the Yankees in their 1999 and 2000 triumphs. He won Game 3 against the Diamondbacks and he did pitch superbly for six and one third innings in Game 7 against Schilling, throwing 6 and a third innings, striking out ten and giving up just one earned run. You can't blame the loss of that series on him.

He did everything the Yankees asked for in the LCS but he was knocked out of the box in Game 7 of the 2003 LCS after three innings. Grady Little and Aaron Boone bailed him out. He didn't help in the six game loss against the Marlins that followed. Then it was off to Houston.

He did help get the Astros further than they ever had in the postseason to that point in their forty-three year history  including their triumph over the reigning National League champion the Cardinals. But he got knocked out against the White Sox in two innings as they broke their 88 year curse.

As Yankees fans remember he came back in 2007 to help them try and win one last ring. In his only start he didn't last three innings as Cleveland romped to an 8-4 win. It must have been a cruel irony that the Red Sox won the World Series that year.

Clemens all told went 12-8 with a 3.75 ERA and struck out 173 players in his 35 postseason appearances. Regardless of steroids he was good in the postseason but its hard to argue he was as good as his overall record.

 

Greg Maddux

Chicago Cubs 1989 NLCS 0-1

Atlanta Braves 1993-2003

NLDS 5-3

NLCS 6-7

World Series 2-3

LA Dodgers 2006, 2008 NLCS 0-0

 

Two things can be true. Greg Maddux is one of the greatest pitchers of all time and he does not have a particularly good postseason record. This is not the only reason that the Braves only managed to win one world series despite winning fourteen consecutive division titles but it is one of them. Because the only three years the Braves made the World Series during Maddux's tenure were 1995, 1996 and 1999 let's focus on them.

1995 was the year of Maddux's fourth consecutive Cy Young award and arguably one of the greatest years any pitcher had in my lifetime. He would end up pitching in the very first NLDS against the Colorado Rockies. He pitched in the opening game and went 7 innings leaving with the game tied 3-3. The Braves would win in the ninth. He then pitched in Game 4 trying to close it out in Atlanta. He wasn't sharp giving up 10 hits and 4 runs in 7 innings but neither was his opponent Bret Saberhagen who was knocked out in the fifth as the Braves went on to win 10-4.

He ended up starting Game 3 against the Reds in the NLCS. Here he pitched better throwing 8 innings of one run ball against David Wells as the Braves won 5-2. The Braves would sweep the Reds in four games.

Game 2 against Cleveland was Maddux's finest hour in the World Series. He pitched a complete game victory, giving up just 2 hits as Atlanta won 3-2. However when he faced off against Orel Hershiser in a rematch in Game 5, he was hit for 4 runs in seven innings as the Indians staved off elimination. It would work out as we'll see in the next entry.

In 1996 the defending champion Braves faced LA in the NLDS. Maddux pitched seven innings of dominant ball in Game 2 as the Braves ended up winning 3-2 in what would be a three game sweep.

In the NLCS the Braves faced off against the Cardinals. In Game 2 the Cardinals trounced Maddux soring 8 runs against him and while only three of them were earned, the Cardinals still won 8-3.  By Game 6 the Braves were behind 3 games to  and facing elimination. Maddux gave them just one run in 7.2 innings as Atlanta won 3-1 and the Braves would face off against the Yankees.

Maddux started Game 2 against Jimmy Key and gave up just six hits in eight innings as the Braves won 4-0. But the Yankees famously rallied and by the time the two faced off in a rematch in Game 6 the Yankees just needed one game to win their first World Series in 18 years. Maddux gave it everything he had and gave up just three runs in seven and two thirds innings. But they were more than enough as the Yankees held Atlanta to just one run and survived a scare in the ninth to give former Brave player and manager Joe Torre his first World Series ring.

In 1999 the Braves faced off against the Astros in the NLDS. Maddux was hammered in Game 1 in what would be the Braves only loss in the series. He would pitch to one batter in Game 3 in what was a twelve inning victory as the Braves won the series 3-1.

In Game 2 of the NLCS against the Mets he pitched the opener and threw seven innings of dominant ball as the Braves won 4-2. He was the starting pitcher in the epic 15 inning Game 5 which the Mets won with a grand slam single but the Braves would ultimately win the series. But in the World Series against the Yankees in Game 2 he was hit for 4 runs in seven innings as the Yankees won 4-1 in what was their second consecutive World Series sweep.

Maddux would never get back to the World Series and the Braves wouldn't for another twenty years.

 

Tom Glavine

Atlanta Braves 1991-2002

NLDS 3-3

NLCS 5-9

World Series 4-3

2006 Mets

NLCS 1-0

NLDS 1-1

Tom Glavine is one of the greatest pitchers of all time and he holds one of the most dubious records of all time. He lost more NLCS games than any pitcher in history – 10. And it is those ten defeats that overshadow an honestly superb postseason record as he went 4-3 in both the NLDS and in five World Series.

If anyone wants to ask why the Braves only won one World Series in their dynasty Glavine has to be considered at least part of the problem. It wasn't as though he ever pitched badly in the postseason: his lifetime postseason ERA is 3.30. And when he was good he was very, very good as the Cleveland Indians remember in Game 6 of the World Series where he held them to one hit in 8 shutout innings.

A lot of the time you see a pitcher who just had terrible luck. In 1991 he went 0-2 against the Pirates and 1-1 against the Twins.  But he lost Game 5 of the NLCS 1-0 and Game 2 of the World Series 3-2.. He went 0-2 against the Pirates in the 1992 NLCS but he lost Game 3 3-2 and he lost Game 4 of the World Series 2-1 against Jimmy Key. In Game 3 of the 1996 World Series he was in a pitcher's duel against David Cone and he gave up just 2 runs in 7 innings.  When he left he was losing 2-1. (The Yankees won 5-2) And in 1998 when he was pitching against the Padres the Braves scored a grand total of zero runs for him against him in two losses. His record for the 1998 postseason was 0-2 with an ERA of 1.92.

Ironically in 2006, near the end of his career, he had better luck with the Mets. With little left but guile he pitched six innings to help the Mets defeat the Dodgers in Game 2 of the NLCS. And he pitched superbly against the Cardinals in the NLCS winning the opener in what would be a 2-0 shutout. He was good for a while in Game 5 but then he was hammered in the fifth as the Mets would lose 4-2 and eventually the NLCS as the Cardinals would go on to win their first World Series in 24 years.

Baseball is a game as much about luck as skill and this was proven the case for both of the Braves 300 game winners.

 

Randy Johnson

Seattle Mariners 1995, 1997

ALDS 2-2

ALCS 0-1

1998 Houston Astros

NLCS 0-1

1999,2001-2002 Arizona Diamondbacks

NLDS 0-3

NLCS 2-0

World Series 3-0

2005-2006 Yankees

ALDS 0-1

Johnson's track record, like so many of these pitchers, is more based on his record against The Yankees rather than with them. And looking at it he was critical in two of their most infamous defeats.

In 1995 with the Mariners facing elimination against the Yankees in the ALDS he pitched 7 innings and struck out ten in what was a 7-4 victory. Then in Game 5 with the score tied he came in to the pitch the final three innings in the game that has gone down in Seattle history. The Mariners won 6-5 which no doubt saved the franchise. He helped them win Game 2 against Cleveland though he wouldn't get credit for the victory. He was in a scoreless duel in Game 5 until Cleveland scored four in the eighth to win and eventually go on to the World Series.

In 1997 he faced off against the ascendant Orioles and would end up losing both games he started. He lost Game 1, getting knocked out of the box in the sixth and while he pitched better in Game 4 Baltimore would prevail 3-1. After that he was off to Houston.

He pitched very well in Game 1 throwing 8 innings and only giving up two runs. But the Astros only scored 1 and he lost. He started against San Diego in what would be the decided game and again got no support despite giving up just one earned run in six innings. Still the Padres won 6-1.

In 1999 the expansion Diamondbacks would make it to the postseason in only their third year of existence. However against the Mets Johnson was subpar. He pitched 8.1 third innings and while he struck out eleven he would be responsible for seven runs as the Mets would end up winning that year before…well, you saw.

But 2001 was his finest hour. Despite the fact he would lost 4-1 against St. Louis the Diamondbacks would win the NLCS. Then against the Atlanta Braves he was magnificent, winning both his starts. He threw a complete game shutout a three-hitter with 11 strikeouts to win Game 1 and then clinched the Diamondbacks first pennant with eight innings that led to a three two victory. And in the World Series he and Curt Schilling destroyed the Yankees. He pitched a second complete game shutout in Game 2 with 11 strikeouts and just three hits. In Game 6 with Arizona facing elimination he pitched seven innings as Arizona destroyed Andy Pettite and his successor 15-2. And then in a moment that would not be seen again until the most recent World Series came in with one days rest to get the final out of the eighth inning to keep the score at 2-1 until the Diamondbacks completely their incredible comeback to win 3-2 and end the Yankees dynasty. He and Curt Schilling tied for the World Series MVP that year.

He was never that good again. The following year the Cardinals trounced him yet again as they got revenge in a rematch of the previous years NLDS and when he came back to the Yankees while he was still a good pitcher he couldn't prevail in the post season. He was only able to last a combined 7-1 innings in two lopsided losses to the Angels in 2005 as the Yankees lost in five and the following year Detroit got to him in for five earned runs by the sixth inning as the Tigers would win the ALDS that year. Still based on his 2001 record alone it's hard to argue The Big Unit wasn't one of the best Big Game pitchers in his prime and considering that five of his postseason wins were against them, it's hard to argue he wasn't a Yankee Killer which is nearly as big a deal.

 

Conclusion

After doing all my homework an obvious conclusion can be drawn. Just because you are one of the greatest pitchers of all time does not mean you will be dominant in the postseason.

Some of these pitchers in any era are subject to luck as much as skill.  Christy Mathewson and Eddie Plank had some of the best overall ERAs in World Series history but both of them managed to lost five games apiece which is among the highest number of all time over a century later. Lefty Grove was almost as good in the World Series as he was in the regular season and the same could be said of Warren Spahn.

And some things do surprise you. No one ever thought Don Sutton was as great a pitcher as Steve Carlton until Sutton was near the end of his career but he was just as good in the clutch as any of the pitchers in his era. And despite the fact that Maddux and Glavine are two of the greatest pitchers I've ever seen they were just as subject to misfortune as any other pitcher.

And let's not forget to be a great postseason pitcher your team has to make it to the postseason. That's the real reason that I think this argument about a pitcher not being great because they made into the postseason is a canard that Yankee fans use to prove their superiority. And that's just crap.

Waite Hoyt and Herb Pennock won five world series games each; neither of them would say they held a candle to Walter Johnson or Grover Cleveland Alexander who pitched against them in pennant races and the World Series. Don Larsen won as many World Series games as Warren Spahn, no one's saying who's the better pitcher. Hell Jerry Koosman is undefeated when he pitched for the Mets in the World Series and he would never say he was better than Tom Seaver.

That's why if I had a game to win and my life depended on the outcome (that's a phrase Red Barber once said to describe why he thought Carl Hubbell was the best pitcher he ever saw) I'd want any one of those pitchers on the mound rather than any of the ones who pitched on the Yankees during their dynasty or even today. Yes I'd want Whitey Ford on my staff too but he'd have been a great pitcher on any team, not just if he wore pinstripes.

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