Ranking the worst stretches in Yankees history

The Yankees are one of the winningest franchise in professional sports history, but this benchmark of greatness is both a blessing and a curse. The standard of winning the Yankees have established puts them in the unenviable position of having the highest possible expectations among their fan base. The barometer of a successful season is a World Series win.

As Andres showed on Tuesday, the Yankees have more to celebrate than any other franchise. They also have plenty of ignominious teams that fans would love to strike from their memories. Some of these teams were embarrassing no matter where you set the bar, while others were successful in some regards but ultimately failed to live up to the lofty expectations they promised.

Without any further ado, let’s look back at the five most disappointing stretches in Yankees history:

5. The Almost decade: 2001-2008

Only by virtue of being the Yankees could a stretch that saw two World Series appearances be called unsatisfactory. However, the failure to capitalize on such a powerhouse roster is what puts this team at fifth on this list.

Coming off their fourth World Series in five years, the Core Four and the Yankees seemed poised for a Murderers’ Row-esque period of dominance. The Yankees should have won at least three more titles in this span, and it is the nature of their postseason exits in 2001, 2003, and 2004 that stings the most.

Losing on the infamous Luis Gonzalez walk-off when they should have been bringing the salve of a trophy home to a wounded city in 2001; to the upstart Marlins in 2003 who had no business beating the Yankees; to Boston in the 2004 ALCS, becoming the only team in history to lose a seven-game series after going 3-0 up. All of these were crushing blows for a team that had a chance at the history books.

4. The changing of the guard: 2010-2019

Again, making the playoffs in seven out of ten years is something the majority of teams would take and run. There is one notorious distinction about this span, though, that puts it squarely at number four on this list. The 2010s was the the only decade since their first World Series victory in which the Yankees failed to make a single Fall Classic appearance.

You might argue that the Baby Bombers have done enough to displace these years from this ranking, however it is precisely their immense talent, and the correspondingly high expectations and failure to meet said expectations that seals their spot on the list.

The 2017-2019 stretch ushered in the the newest wave of young homegrown stars, and concluded with three straight playoff appearances, yet the Yankees were clearly the second-best team in all three series they lost (cheating notwithstanding). The rebuilt franchise certainly promises plenty more excitement in the coming years, but the lack of a World Series appearance cannot be ignored. In fact, given the strength of the roster, the playoff stall-outs can justifiably be considered disappointments.

3. Steinbrenner’s stuggles: 1982-1995

The lean years between the Bronx Zoo and the Core Four is a span that I am sure many readers of this site look back on with regret. The Yankees had three of the greatest offensive threats in the game for a solid chunk of these years, yet made only a single playoff appearance at the very end.

If you gave me a team with Don Mattingly, Dave Winfield, and Rickey Henderson, I would tell you that team should be in the World Series every year. That trio certainly gave Yankees fans a lot to cheer about in the 80s, including the memorable 1984 batting crown race between Mattingly and Winfield, Mattingly’s 1985 MVP campaign, and Rickey’s otherworldly 1985 season. However, their lack of any postseason appearances in their prime years will forever remain a sour note of their Yankees legacies.

2. The CBS years (plus a few more): 1965-1975

After losing to the Cardinals in the 1964 World Series, the Yankees would not make another World Series appearance for the next decade. The first half of this span saw Mickey Mantle limp to his retirement, during which the Yankees never finished higher than fifth in the AL. And while the second half saw the emergence of future captain Thurman Munson, the Yankees finished at least ten games back more often than not. These rainy days eventually led to greener pastures with the sale of the team in 1973, but still marked the end of nearly half a century of dominance.

1. Stumbling out of the starting blocks: 1903-1920

There’s no way to sugarcoat this: before Ruth and Gehrig got to town, the fledgling Yankees were bad. Really bad. Like, stick your head in the sand bad. The Highlanders, and then the Yankees, failed to register a single playoff appearance in the first 18 years as a franchise. They had a .485 winning percentage during this span, and even finished 55 games back of first place in 1912. Their best player during this era? Shortstop Roger Peckinpaugh, who turned in a single 5+ WAR campaign in 1919. The bitter taste of these early years was washed away by the torrent of success of Murderers’ Row and future dynasties, but this mighty franchise certainly had humble beginnings.