5 Times the Yankees Won the Pennant, But Shouldn't Have (And 5 Times They Didn't, But Should Have)

Sometimes, the better team doesn't win. Sometimes, the more deserving team doesn't win. Frequently, the Yankees are the more deserving team. But, in the immortal words of Clint Eastwood, "Deserve's got nothin' to do with it."

5 Times the Yankees Won the Pennant, But Shouldn't Have -- And...

5 Times They Didn't, But Should Have

These are in chronological order, rather than alternating between "Should Have" and "Shouldn't Have":

10. Should Have: 1904. For the first time, and not for the last, an American League Pennant comes down to New York and Boston. The last day of the season features a doubleheader at Hilltop Park, at 165th Street & Broadway in Manhattan's Washington Heights.

The New York Highlanders, forerunners of the Yankees, need to sweep the Boston Americans, forerunners of the Red Sox, in order to win. Otherwise, Boston will win it. Hilltop Park seats about 16,000, but there's perhaps 30,000 jammed into the confines, including thousands of standees roped off in the massive outfield area.

Pitching the 1st game for the Highlanders is Jack Chesbro, who has already won 41 games, which remains the single-season record for pitching from 60 feet, 6 inches away. And that's pronounced CHEESE-bro, not CHEZ-bro.

With the score 2-2 in the top of the 9th and Lou Criger on 3rd base, Chesbro throws a spitball – then a legal pitch – but it's a wild pitch, going over the head of his catcher, Jim "Deacon" McGuire, and Criger scores the Pennant-winning run. The Yankees win the nightcap, 1-0, but it's meaningless, as the Red Sox-to-be win the Pennant.

9. Shouldn't Have: 1922. The only time the St. Louis Browns won the Pennant, before moving in 1954 to become the Baltimore Orioles, was in 1944. But their 1922 team was considerably more talented, and also won more games, 93, compared to the 88 they won in 1944. But they lost the Pennant to the Yankees by 1 game.

The Browns nearly won it because Babe Ruth had spent much of the season squandering his great talents with carousing; and also because they had a pitcher the Yankees traded away to them, and would later reacquire, Urban Shocker. That trade nearly cost them the Pennant in 1921 and 1922, and it probably did cost them the Pennant in 1920 and 1924. They got him back, and he was key to winning the Pennant in 1926 and 1927.

8. Shouldn't Have: 1955. They finished 3 games ahead of the Cleveland Indians, despite being in kind of a transition between the teams of the Reynolds-Lopat-Raschi rotation and Phil Rizzuto at shortstop, and the Mickey-Yogi-Whitey teams of the late 1950s.

Plus, the Naps/Indians/Guardians have only won 6 Pennants in 123 years. And while it wouldn't have meant quite as much for the Brooklyn Dodgers to win their one and only World Series by beating Cleveland, it would have meant more to the Yankees to not have been the team they beat.

7. Should Have: 1980. Talent-wise, the Kansas City Royals have never been a better team than the Yankees, except maybe in 2014. (No, not even in their World Championship seasons of 1985 and 2015.) Certainly not in 1980, when the Yankees had a much tougher Division. (They won 103 games, and still beat Baltimore by only 3 games; K.C. won 97, and were 14 ahead of Oakland.) Plus, the Royals were as dirty as ever that season. Seriously: You'd have to be a hardcore hick to believe that George Brett ever deserved to win a Pennant.

6. Should Have: 1986. Maybe they were better in 1985, and getting revenge over the Royals for '80 would have felt great. But I'm going for '86. The California Angels proved they were there for the taking. And it would have set up a Subway Series with the Mets. And Dave Righetti was no Calvin Schiraldi -- or Bob Stanley. And Don Mattingly was no Bill Buckner. It would have humiliated the Met fans to see their "inevitable" World Championship ruined, by the team they hate the most, at their Flushing Toilet. As happened in 2000, although the Yankees did enter that Series as the favorites.

Interlude: 1994. Acting Commissioner Bud Selig screwed the Yankees over that season, but then, he screwed over a lot of teams, especially the Chicago White Sox, the Cleveland Indians, and the Montreal Expos. I can't say the Yankees deserved to win it more than those teams did.

5. Shouldn't Have: 1996. This might be sacrilege, but the Yankees did kind of limp into the Playoffs, nearly blowing the AL East title to the Orioles, and coming damn close to going down 2 games to 0 to the Texas Rangers in the AL Division Series. Throw it the Jeffrey Maier play in Game 1 of the AL Championship Series against the Orioles, and how badly they were beaten in the 1st 2 games of the World Series against the Atlanta Braves, and, arguably, the Yankees were really, really lucky.

Then again, they'd been really unlucky in the preceding 15 years. So, in this case, "Shouldn't Have" is a bit of a stretch.

4. Shouldn't Have: 2000. Yes, we beat the Mets in the World Series, and it was wonderful. It was also nerve-wracking, and probably took a year off my life. And we lost 16 of 19 heading into the Playoffs, nearly blowing the Division to the Red Sox. And we nearly blew the ALDS to the Oakland Athletics. Maybe if the A's had won the Pennant, they would've gotten a new ballpark, and wouldn't now be in danger of moving to an antiseptic airplane hangar in Las Vegas.

3. Shouldn't Have: 2003. Of all the Yankee teams accused of using performance-enhancing drugs, this one is the most-accused. Who knows: If Aaron Boone doesn't hit that home run, then, with Mariano Rivera done for the night, the Yankees probably lose the game in the 12th inning or onward; the Red Sox get out-cheated by the Florida Marlins (remember: They had steroid cheat Iván Rodríguez), and maybe they then fall apart, and don't win the Pennant and the World Series in 2004 and 2007, and we're still chanting "1918!"

Also, if Boone doesn't hit that home run, he probably never gets named manager of the Yankees.

2. Should Have: 2011. It all seemed to be coming together. Derek Jeter got his 3,000th career hit. Mark Teixeira and Curtis Granderson each hit 39 home runs, while Robinson Canó had 28, and each of them had at least 111 RBIs. CC Sabathia went 19-8, and Iván Nova went 16-4, notching the most wins by a Yankee rookie pitcher in 43 years. Best of all, they came from behind to win the Division, while the Red Sox had yet another September collapse, and missed the Playoffs completely.

And then the Yankees lost the AL Division Series to the Detroit Tigers. Their 3 losses were by a combined 4 runs. Nova was injured, but Joe Girardi started him in the decisive Game 5, anyway, and he could only go 2 innings, allowing 2 runs. Had Girardi started Phil Hughes, the Yankees would have won. The Pennant and the World Series were there for the taking: Neither the Texas Rangers nor the team that beat them in the World Series, the St. Louis Cardinals, was particularly impressive.

1. Should Have: 2017. Not just because it was Aaron Judge's rookie year and he hit 52 home runs. Think of how many Yankees looked like the wave of the future, and ended up massive disappointments and heartily booed. Gary Sánchez. Aaron Hicks. Didi Gregorius. Luis Severino. Dellin Betances. Chad Green. Domingo Germán. Not to mention the veteran Jacoby Ellsbury.

It ended up a waste of great seasons by Judge, Sánchez, Gregorius, Green, Sabathia, David Robertson, Brett Gardner, Starlin Castro and Matt Holliday. It was also the last, best chance for Masahiro Tanaka, who didn't have such a great season. Nor did Aroldis Chapman, who, at the least, won it the previous season with the Chicago Cubs.

They didn't win the AL East, but beat the Minnesota Twins in the AL Wild Card Game, came from 2-0 down to beat Cleveland 3-2 in the AL Division Series, and came from 2-0 down to lead the Houston Astros 3-2 in the AL Championship Series.

But they needed to win a 4th game in Houston, and, in Games 6 and 7 combined, went 10-for-63, a .159 batting average, against Justin Verlander (whom general manager Brian Cashman refused to acquire from the Detroit Tigers, and let the Astros get him) and Charlie Morton. And the Astros scored 11 runs in those 2 games -- by cheating, as we later found out.