Top 10: Most Disappointing Moments in Yankees History

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July 16, 2013 by NowhereButPop

By Andrew Doscas

As I write this bear in mind that the Yankees are in fourth place in the AL East, and will in all likelihood fail to make the playoffs.  This makes me angry.  So I decided that the best way to overcome my present discontent with the 2013 Yankees is to sit and stew over Yankee failings of the past.  Also note that most of the following moments occurred during the playoffs, after all we’re not like the Royals, winning is an expectation, not a fluke.

10) July 1st, 1990

            In a miraculous summation of the failures and ineptitudes of the late 80s-early 90s Yankee teams, Andy Hawkins no-hitter serves as the icing on the cake to the darkest time in Yankee history.  Oh, I forgot to mention that he was losing pitcher in his own no-hitter.  Even though Hawkins gave up a total of 0 hits, the Yankees still lost to the White Sox 4-0.  Not only did they lose a no-hitter that their pitcher threw, they managed to allow four runs to cross the plate.  This is what the Yankees had become by 1990…a calamity.

9) December 13, 2007

The day that the Yankees were effectively held up, will forever serve as a cautionary tale to all Yankee fans.  After Alex Rodriguez opted out of his contract, instead of letting go of a player who routinely tanked in the playoffs, the Yankees decided to give him a ten year deal worth a quarter of a billion dollars.  Not for nothing but this is the Yankees we’re talking about; we don’t take shit from no one.  After the contract was signed, A-Rod has never and will never claim another MVP award, play another full season with injury or possible suspension (fingers crossed), or done anything to make the fans not hate him.  He had one good postseason outing in 2009 but after that reverted to type every subsequent year.  This is why you don’t over pay a player based on what he’s done in the past instead of what he will produce in the future.

8) Every bad trade the Yankees ever made between 1982-1990

Here is a short list of former Yankee prospects who were traded away.


Traded For

Eventual Accomplishments

Jay Buhner

Ken Phelps

310 Home Runs

964 RBIs

Fred McGriff

Dale Murray/Tom Dodd

5x All Star

493 Home Runs

1550 RBIs

2x Home Run Champion

1x World Series Champion

Doug Drabek[1]

Rick Rhoden

1990 NL Cy Young Winner

Al Leiter

Jesse Barfield

2x All Star

1974 K’s

3x World Series Winner

Willie McGee

Bob Sykes

1985 NL MVP

2x Batting Champion

4x All Star

1x World Series Champion

7) The 1960 World Series

The Yankees outscored the Pirates 55-27, batted .338 as a team compared to the Pirates .256, and Whitey Ford pitched two complete game shutouts, and they still lost to a Pirate’s team that was nowhere nearly as good.  Manager Casey Stengel (who was probably too senile for his own good at that point) effectively lost the series for the Yankees by purposely sitting out Whitey Ford until game 3.  Mickey Mantle once said that his two biggest regrets as a player was not hitting .300 for his career and losing to the Pirates in 1960.  Mantle, who had lost in the World Series before, actually cried after game 7 because he felt that the better team hadn’t won.  He was right.  This was also the first sign of the eventual collapse of the original Yankee dynasty.

6) The 1980 ALCS

Not only did we have the best record in all of baseball that year, but we had beaten those assholes in the playoffs three consecutive years from 1976-1978.  The Royals win over the Yankees not only came in a sweep (the third such time the Yankees were even swept in the playoffs), but it also cemented George Brett as being public enemy #1 in New York…well at least until Reggie Miller came along.  What makes matters worse is how they lost.  Bonehead coaching decisions cost the Yankees game 2, and Goose Gossage, the best closer in baseball at the time gave up the series winning hit to who else, George Brett.  As the 1960 World Series marked the beginning of the end for the Yankee golden age, so did the 1980 ALCS mark the beginning of the end for the late 70s dynasty.

5) The 2003 World Series

What could have been one of the most gratifying ways to end a rough and turbulent season instead went horribly awry after game 3 of the World Series.  Image the satisfaction of the ALCS that year, capped off with another championship.  Unfortunately, fate would not be so kind.  For those who don’t know, the 2003 World Series against the Florida Marlins is the Yankees version of Vietnam.  The Yankees are the juggernaut, the powerhouse, up against this shitty little team that no one cares about, that just barely squeaked by.  They were a team that needed divine intervention to make the World Series.  Savior of the ALCS Aaron Boone couldn’t get it done in the World Series in game 4 where a fly ball would have given the Yankees the lead in extra innings, and David Well’s back couldn’t support his fat ass in game 5.  The World Series blew up in our faces, and the loss still haunts us, because we lost to a worse team, a team we should have crushed.  I don’t know about most fans, but knowing what I know now I’d say let the Red Sox beat us in the ALCS that year just so they could have the indignity of losing to the Marlins.  After all what’s the point of going to the World Series, if you’re not gonna win it?

4) The 1981 World Series

Which brings us to the next one on our list…the 1981 World Series.  Similar to number 6, here, we faced a familiar foe, one whom we had vanquished before, and were expected to do so once more.  Not only is the loss bad enough (remember we were up 2-0 in the series), it was also the work stoppage that robbed the Yankees of their momentum.  He real twisted thing though is that they got it back during the ALCS where they swept the A’s and carried it into the World Series.  The turning point came in game 3, where they had multiple chances to take the lead, knock Fernando Valenzuela out of the game, and take a 3-0 lead in the series.  The clincher however came in game 6 when Steinbrenner ordered manager Bob Lemon to take starter Tommy John out of the game for no reason….The Yankees were leading the game at that point.  Oh yeah and Dave Winfield batted a sickening .045.

3) August 12th, 1994

Here it was, our best chance to make the playoffs for the first time since 1981, and for the first time in Don Mattingly’s career.  And then it was wiped away because of money and greed.  We had the best team in the AL that year and were the favorites to go to the World Series and lose to the Montreal Expos.  The strike was the final insult to the futility of the 80s-early 90s; it somehow upheld and even justified all the shitty seasons and stupid decisions.  But at the same time, had it not been for the strike the most recent dynasty might not have happened.

2) The 2004 ALCS

Some things should just never happen.  One of which is a team blowing a 3-0 lead, especially to the most hated of rivals.  No team (save for the Red Sox) should have to go through that.  So many things are wrong with this scenario.  A 3-0 lead now makes me incredibly apprehensive (which it shouldn’t at all…ever), every Red Sox fan now has that to hold over us, Mariano failed to get the job done, and it had to be to the Red Sox, the shittiest, prick-ist bunch of morons ever assembled for money.  For as long as I live this question will plague me: How the fuck are you going to blow a 3-0 lead in a playoff series?  I fear I may never know the answer to this question.

1) The 2001 World Series

Let me just preface this by saying that as Yankee fans, we have a sense of entitlement when it comes to winning, we do, and with good reason.  We’ve won it all 27 times in 90 years, there’s no reason why we can’t win 27 more in 90 years…after all we’re the fucking Yankees.  The team has more net value than probably 30% of the world’s nations.[2]  We have to win, we don’t need to.  The Cubs are a team that needs to win, but not us.  Winning is an expectation, not a pleasant surprise, or something to shoot for once and a while.  But the one time that they needed to win, off the heels of 9/11, they failed us.  Not only that but even the ride to get to the deciding game 7 was so thrilling and magical that there was no way we could lose it after going through what we did.  The Derek Jeter flip play in the ALDS, beating the 116-win Mariners in the ALCS, the late game heroics in games 4 and 5 of the World Series, the send off to Paul O’Neill, and the Soriano home run in game 7 all became for naught in the bottom of the ninth as Arizona, of all the teams, rallied to win the series.  Bad enough it came off of Mariano Rivera, who’s really only failed in the playoffs three times, but when he needed it the most, and with victory within our grasp, they let us down.

[1] On the flip side, Drabek somehow managed to blow out his arm with an 89 mph fastball, so it might not have been a total loss.

[2] This is a fictional statistic, but I can’t imagine I’m too far off.


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