top of page
  • Writer's picturePaul Semendinger

Why Do The Yankees Fall Short in the Playoffs?

by Paul Semendinger

May 18, 2023


As happens often, we had some great discussions/debate in the comments of a recent article. This article asked our writers to comment on Brian Cashman's job performance.

Some Yankees fans (many?) are frustrated by the Yankees' inability to reach, and/or win, a World Series since 2009. It's been a long time since the Yankees were there.

Brian Cashman has been the General Manger for this entire period. Because of this, many blame him and his decision-making for the Yankees' failure to reach the World Series. It's a fair argument. The results speak for themselves.

In the piece, I argued that Brian Cashman, overall, has been a good GM, but, the fact that his teams haven't reached the World Series can't be ignored. I wrote:

"Brian Cashman has done an excellent job for the Yankees. The Yankees are in the playoffs almost every year. They have had a winning record for the last three decades. The last time the Yankees failed to have a winning season was 1992. Holy cow! That's a long time ago. There is a lot that has gone right.

(In short...) Brian Cashman has been a great GM at building teams that are better than .500 (often much better) and that reach, but fail, in the playoffs. That's his legacy. Overall, compared to every other franchise, that's great. For the Yankees, it's not good enough."

I have even argued that Brian Cashman has been a Hall of Fame worthy General Manager. He has been that good. But he has not been good at building teams that reach or win World Series. That is also very true. It's an absolute fact that cannot be argued away because, in short, the Yankees have not reached many World Series during Brian Cashman's long tenure, especially since 2004. (The Yankees have been to one World Series since then.)

In the comments, I noted that lots of other teams have figured out how to reach the World Series:

"Since 2010, the Giants, the Rangers, the Cardinals, the Tigers, the Red Sox, the Royals, the Mets, the Cubs, the Indians, the Astros, the Dodgers, the Nationals, the Braves, the Rays, and the Phillies have all reached the World Series."

That's a lot of teams who figured it out. The Yankees haven't - for a long time.

One reader put forth the idea that it's more difficult for the Yankees to reach the World Series because Major League Baseball has designed a system that prevents teams from being able to dominate over long periods.

First, if that's true, what's also true is that the Yankees haven't dominated in a long time. As I have shown, a host of teams have made it to the World Series, but not the Yankees.

But that premise is factually wrong anyway because there have been teams that have dominated. To that point, I showed two very clear examples where franchises have been able to reach the World Series multiple times in recent years:

"Houston Astros:

2017 - World Series Champs

2018 - Reached ALCS

2019 - Reached World Series

2020- Reached ALCS

2021 - Reached World Series

2022 - World Series Champs

The LA Dodgers have been in the playoffs every year since 2013. They've also been in three World Series, winning one."

I have to ask, if those other teams can do it, why can't the Yankees? (And to the main point, I haven't asked why the Yankees haven't reached multiple World Series... just one.)

Are the rules stacked against the Yankees? I don't think so. As such, it must be something else. It's not Major League Baseball's rules or structure preventing the Yankees from greatness.

A different argument claims that it's the random nature of short playoff series that has prevented the Yankees from reaching the Word Series.

I also don't buy that excuse. I don't buy it for two major reasons. First (as I wrote),

"Since 2010, the Yankees, have gone 31-36 in the post season.

Yes, in the post season, they are five games under .500 since 2010.

The following team have eliminated the Yankees in the post season: Texas Rangers, Detroit Tigers (2 times), Houston Astros (4 times), Boston Red Sox (2 times), and the Tampa Bay Rays.

Is this a case of just random bad luck?

Can this be attributed to the small sample sizes of the various playoff series?

Or has there been a flaw in the Yankees design/roster construction for post season play for well over a decade?"

A short series might be a small sample size, but 67 games is certainly not a small sample. The "small sample" argument is an easy way to give the Yankees an excuse for losing, but it's been too many games and series for too long to just be randomness or bad luck.

If that argument is true, that short series are meaningless and the winners are all just random, then, by definition, one would have to discount all of the Yankees' World Championships under Casey Stengel (from 1949-1960). In that period, the Yankees played 63 total World Series games. If the randomness of short series is the main (or only) factor in a team winning or losing, than all those championships would have to be attributed to random luck. In other words, the Yankees under Casey Stengel were not as great as they seemed, they were just the luckier team year-after-year in the World Series. (Joe McCarthy's teams played in only 38 World Series games.)

The randomness argument eliminates the entirety of baseball history by changing the narrative from teams and players being great to teams and players being nothing more than super lucky. How could Babe Ruth have been a winner? He played in only 41 post season games. Lou Gehrig played in only 34. (If skill has noting to do with winning, and it's all just random chance, then Lou Gehrig wasn't truly great and, indeed he was "The luckiest man on the face of the Earth".)

And if 67 games isn't enough of a sample, then 62 swings absolutely can't mean anything. (Sorry Aaron Judge, those homers... just random chance. )

If we take this thought to its logical conclusion, and apply it to another sport, the entire history of the Super Bowl is meaningless. It's just one game, nothing is proven in just one game. In fact, there haven't even been 60 Super Bowls yet.

No, it is absolutely something more.

Secondly, as I have argued before, one might be able to claim that it has been the randomness of short series or bad luck preventing the Yankees from winning if the Yankees were always the better team that lost in the playoffs, but that also hasn't been the case, not for a long time.

In short, when the Yankees have lost in the playoffs, they lost to a better team.

Most often the teams the Yankees lost to were better - they had better regular season records. By definition, the better teams actually won. That's not "chance" or "randomness," or bad luck. That's what is supposed to happen. The better teams, even in the expanded playoffs, are most often supposed to win.

Here are the facts, year-by-year since 2017:

  • 2017: The Yankees (91 wins) lost to the Astros (101 wins) - The better team won

  • 2018: The Yankees (100 wins) lost to the Red Sox (108 wins) - The better team won

  • 2019: The Yankees (103 wins) lost to the Astros (107 wins) - The better team won

  • 2020: The Yankees (33 wins) lost to the Rays (40 wins) - The better team won

  • 2021: The Yankees (92 wins) lost to the Red Sox (92 wins) - There wasn't a better team

  • 2022: The Yankees (99 wins) lost to the Astros (106 wins) - The better team won

I cannot comprehend how there can be a narrative that the Yankees, who have continually lost to superior teams, can be said that they lost because of random chance.

In fact, the random chance should have helped the Yankees. It should be that it is in a short series, with the luck and randomness that brings, the better team should sometimes lose. But with the Yankees, that hasn't been the case. The better teams continually defeat them. That's not random. That's not bad luck. That's how it's supposed to work.

Even in 2021, had Yankees defeated the Red Sox (an equal team), they would have still had to face the Rays, who were, again, the better team. The Yanks won 92 games in 2021, the Rays won 100. If the Yanks had defeated the Rays, the Astros (95 wins) who came next, were also the better team.

The fact that the Yankees have not reached the World Series is because there is a flaw in the teams the Yankees are building.

Brian Cashman's Yankees seem content with "good enough." They don't seem to be aiming for greatness. As much as all the regular season wins, and the long history of better than .500 seasons, and all the playoff appearances, this is Brian Cashman's legacy. He builds good, but not great teams.

The Yankees have been very good for a long time. But they also have not been great for a long time.

The facts speak for themselves, the Yankees have not been the best team, by record or results, not just in baseball, but even in the American League, for a long long long time.

There is only one logical answer for this. Only one. It hasn't been MLB's rules or random luck, that has prevented the Yankees from reaching (and winning) the World Series, it's been that the Yankees, under Brian Cashman, as good as he has been as a General Manager, have not built great teams. The Yankees' overall design is flawed.

The reason the Yankees have lost in the playoffs is simple. It is because they did not build teams good enough to win in the playoffs.

43 Kommentare

18. Mai 2023

Hal Steinbrenner says season is not a failure if Yankees don’t win World Series

Gefällt mir

18. Mai 2023

Seems like everyone is arguing statistics. The trouble lies in the roster construction. The best comparison I can make is the Jeter, Rivera, Posada, Tino, O'Neill teams that were balanced to perfection. These guys had winners' attitude, did not strike out, took pitchers deep into the count, made productive outs, were excellent defensively, hit enough homers, and just refused to lose. Lose, they did but not very much. And I do not attribute that to Joe Torre. I give the credit where it is due: to Stick and Bob Watson. This is where Cashman does not make the grade. His teams do not play wining baseball against he best teams (see above for CP's definition of winning baseball). Sure, …

Gefällt mir
19. Mai 2023
Antwort an

Agree 100% on roster construction and as Paul pointed out the better teams usually wins. Yankee teams under Cashman have been good 90+ but never the better team to win it all except for 2009 The Cashman era for the Yankees and fans will be defined by his record which is very good but not good enough with only 1 WS title in his 20plus years!

Gefällt mir

Robert Malchman
Robert Malchman
18. Mai 2023

OK, so we've finally pinned things down to 2010-22. Let's look at some records for comparison:

Astros, missed playoffs six times (including three straight years of sub-.400 play, during the tanking period). They won 2 WS (one, at least, by cheating), but also lost one ALDS, two ALCS and one WS.

Dodgers, missed playoffs three straight years, won WS once, lost it twice, lost three NLCS and four NLDS.

Giants, won three WS (outstanding), but lost two NLDS, and missed playoffs EIGHT times.

Red Sox, missed playoffs EIGHT times, won WS twice, lost ALCS once, ALDS twice.

Indians, missed playoffs SEVEN times, lost one WS, lost three ALDS, two ALWC.

So really, the only place the Yankees come up short…

Gefällt mir
19. Mai 2023
Antwort an

1000% correct in your evaluation..... Cashman's template for roster construction has left much to be desired and his results have produced " many good teams" but only the 1 WS win! The Cashman Era is ONE WS ring. The reasons for only the one are many but ultimately the onus is on GM. The better teams win and only once have they had the better team.

Gefällt mir

18. Mai 2023

I believe if you give $200+MM to most executives in Baseball today, they will construct a team that can win 90+ games and a round of playoffs. The true indicator of a top tier GM is winning the Championship and playing in a world series. Cashman failed to do so for 14 years and counting. What he should do, is take over a team like the Pirates or Royals and show us all how great he is, and win 90+ with a $80MM payroll. He has become the Phil Jackson of MLB!

To answer your question Paul, they haven't won because they are built each year for YES ratings and clicks, not Championships. They know NYY fans will be back…

Gefällt mir
19. Mai 2023
Antwort an

Nice post….. and for the Cashman fan boys …. the truth hurts!

Gefällt mir

Paul Semendinger
Paul Semendinger
18. Mai 2023

The question I am asking, which I have not received a direct response to from most of the comments below, is:

Why haven't the Yankees reached or won a World Series since 2009?

What is the reason?

Gefällt mir
19. Mai 2023
Antwort an

You failed to mention the WS championship in 2009 and despite all the winning it's still only ONE WS Ring................ BRIAN CASHMAN is the reason!

Gefällt mir
dr sem.png

Start Spreading the News is the place for some of the very best analysis and insight focusing primarily on the New York Yankees.

(Please note that we are not affiliated with the Yankees and that the news, perspectives, and ideas are entirely our own.)


Have a question for the Weekly Mailbag?

Click below or e-mail:

SSTN is proudly affiliated with Wilson Sporting Goods! Check out our press release here, and support us by using the affiliate links below:

Scattering the Ashes.jpeg

"Scattering The Ashes has all the feels. Paul Russell Semendinger's debut novel taps into every emotion. You'll laugh. You'll cry. You'll reexamine those relationships that give your life meaning." — Don Burke, writer at The New York Post

The Least Among Them.png

"This charming and meticulously researched book will remind you of baseball’s power to change and enrich lives far beyond the diamond."

—Jonathan Eig, New York Times best-selling author of Luckiest Man, Opening Day, and Ali: A Life

From Compton to the Bronx.jpg

"A young man from Compton rises to the highest levels of baseball greatness.

Considered one of the classiest baseball players ever, this is Roy White's story, but it's also the story of a unique period in baseball history when the Yankees fell from grace and regained glory and the country dealt with societal changes in many ways."


We are excited to announce our new sponsorship with FOCO for all officially licensed goods!

FOCO Featured:
carlos rodon bobblehead foco.jpg
bottom of page