📌 Join the BPCrew Chapter in your city and meet up with more Yankees fans! 👉 CLICK HERE

Power Ranking the ‘Jeter Era’ Yankees Championships

The Jeter Era Yankees — 1996 through 2014 — won five championships (breaking news, I know). Every flag flies forever and apparently no matter what you do, they can’t take away that “piece of metal,” but you know as well as I do that not every championship is created equal.

Just think how fortunate we are as Yankees fans to be able to have this conversation. If a Mets fan is reading this in self-loathing hatred, they  would probably spit in my face for even suggesting what I’m about to do. But here we go… I’m going to power rank the five Yankees championships in the Jeter Era.

Embed from Getty Images

Methodology

I’m not ranking which team is best. This is more about what the championship means. Fans have different memories of each title because they happened at different points in their life. I’ve met people through Bronx Pinstripes who cherish the 2009 title because they were too young to remember when the Yankees dominated baseball in the late-90s. I was 8 when the Yankees won in ‘96, so most of what I remember from that championship is through reading stories and wearing out the World Series VHS, but I do have vivid memories of watching the final out with my dad. The first real sports heartbreak I had was in 2001. I honestly thought there was a glitch in the matrix when Luis Gonzalez’ bloop fell. I have my reasons for how I ranked them below, and we’ll get to that in a minute, but first, here are the completely subjective questions I considered when making the rankings.

Was the championship expected?
How difficult was the postseason run?
Was there a ‘holy crap’ moment?
How often do you rewatch the moments from that season?
What were the ramifications of the Yankees not winning?

Now, to the rankings!

#5 – 1999: The Forgotten One

This is the forgotten championship sandwiched between The Greatest Team Ever and The Subway Series. Heck, the Yankees didn’t even do a 20th anniversary ceremony for it to sell a couple thousand extra tickets on an August game nobody wants to go to.

The talent on the 1999 Yankees was every bit as good as the 1998 team, they just didn’t bulldoze their way through the regular season quite as forcefully as the ‘98 squad did. In the postseason they annihilated opponents: 3-0 sweep of the Rangers in the ALDS, 4-1 gentleman’s sweep of the Red Sox in the ALCS, and a 4-0 sweep of the Braves in the World Series.

Was the championship expected?
Yes.

How difficult was the postseason run?
They beat Boston, so that’s cool, but them winning was never in doubt.

Was there a ‘holy crap’ moment?
Does Pedro throwing Zimmer to the ground count? (UPDATE: This was 2003… further proof that the ’99 run should rank 5th. I can’t believe I messed that up.)

How often do you rewatch the moments from that season?
I’m having a hard time even thinking of one to Google.

What were the ramifications of the Yankees not winning?
This is the only argument for the ’99 championship not being ranked 5th: Had they lost to Atlanta, perhaps the Yankees wouldn’t have been crowned ‘Team of the Decade,’ but do you really care about that made-up title?

The bottom line is the ’99 championship is the one I have the least fond memories of. Maybe that’s just because Chad Curtis was on that team…

#4 – 2009: The Expensive One

What does a $2.3 billion stadium, a $161 million ace, a $180 million first baseman, and a $82.5 million mistake add up to? A World Series Championship baby!

Embed from Getty Images

Maybe this title would have more weight had the Yankees won another title in the 2010-12 run, but they didn’t, making this championship really the last hurrah of the Jeter-led Yankees. Hideki Matsui got his signature Yankee moment, ARod got the monkey off his back, and we got to watch watch Jeter, Posada, Rivera, and Pettitte get another ring together.

Was the championship expected?
It was championship or bust after signing Sabathia, Teixeira, and Burnett.

How difficult was the postseason run?
The MLB postseason schedule allowing the Yankees to use a 3-man rotation because of an off-day between game’s 4 and 5 of 7-game series offset any difficult of having to beat the defending champion Phillies.

Was there a ‘holy crap’ moment?
There were actually a few, and they came off the bat of Alex Rodriguez, who slugged 5 homers, drove in 18 runs, and posted a robust .500 OBP in 15 games.

How often do you rewatch the moments from that season?
Occasionally I’ll throw on Matsui’s Game 6 highlights or ARod’s go-ahead double vs Philly. At least they are in high definition. 

What were the ramifications of the Yankees not winning?
Imagine the complaining about expensive contracts if the Yankees didn’t have this title to show for it?

#3 – 1998: The Greatest One

The 1998 Yankees are on a short list of teams that you can argue was the greatest baseball team ever. Had the season not ended in with a championship, they’d be one of the biggest chokers ever. Had they face a more compelling opponent than the Padres, maybe this title would be #2.

Was the championship expected?
Duh.

How difficult was the postseason run?
The playoffs would have been downright boring if it weren’t for Chuck Knoblauch’s inexplicable play in Game 2 of the ALCS, allowing Cleveland to tie the series and eventually take a 2-1 lead heading to Game 4.

Was there a ‘holy crap’ moment?

How often do you rewatch the moments from that season?
This is the area where the ’98 run is lacking. There wasn’t much drama because the Yankees were just too damn good.

What were the ramifications of the Yankees not winning?
114 regular season wins would have been for naught. Just ask the 2001 Mariners about that.

#2 – 2000: The Subway Series … one

The 2000 team was not great. I don’t know if it was fatigue from the previous two seasons of dominance or the age/regression from the pitching staff, but the 2000 team limped to 87 wins and somehow turned it on in the playoffs.

Was the championship expected?
A 13-17 September record and season run-differential of just +57 left some serious doubt entering October.

How difficult was the postseason run?
It took them 5 games to beat Oakland in the ALDS and 6 games to top Seattle in the ALCS. The Mets ended up being their easiest opponent.

Was there a ‘holy crap’ moment?
The Todd Zeile/Timo Perez relay play in Game 1 of the World Series. You can always count on the Mets being the Mets.

How often do you rewatch the moments from that season?
I watch for peak Derek Jeter highlights. He put the team on his back and took the series by the balls and the Yankees never looked back. 

What were the ramifications of the Yankees not winning?
Imagine winning in ‘96, ‘98, and ‘99 and then losing to the crosstown Mets? No way. It was a championship they had to win because of the opponent.

#1 – 1996: The First One

You never forget your first. The 1996 Yankees were ahead of schedule. It’s the only championship of the Jeter era where you can say they overachieved — the ‘96 Braves should have won. If the Yankees didn’t go on to win three more World Series in four years, Atlanta would be kicking themselves for losing this series even more than they probably already do. The Braves had no shot in ‘99, but were on their way to establishing a dynasty of their own in ’96.

The 1996 Yankees were much different than the teams discussed above. We didn’t know what the “core 4” was yet. Jeter was a rookie. Pettitte was in his second season. Mariano his first full season as a reliever (John Wetteland was the closer … yikes). Posada wasn’t on anyone’s radar. Tino was not beloved because he replaced Mattingly. Bernie was their best all-around player. Mariano Duncan hit .340 — wait, what?

Was the championship expected?
Hell no.

How difficult was the postseason run?
The Yankees got hot at the right time, beating the Rangers in 4 and Orioles in 5 (aided by a kid). But I cannot understate how good the mid-90s Braves were. They had a 3.52 team ERA when the league average was 4.21.

Was there a ‘holy crap’ moment?
Jim Leyritz’s game-tying homer, Joe Girardi’s triple, the Jeffrey Maier play, Pettitte-Smoltz pitchers’ duel… there are so many from this run. And let’s not forget Wade Boggs riding the horse!

How often do you rewatch the moments from that season?
A billion times.

What were the ramifications of the Yankees not winning?
It’s not hard to imagine a scenario in which the Yankees get trounced by the Braves, Torre gets fired, and Steinbrenner demands they trade Pettitte and Posada for Ken Caminiti (RIP). I don’t want to live in that alternate timeline.

In 2001 the Yankees were 3 outs away from a four-peat, and had they won, I’d have ranked that championship #1 because all it had was ‘holy crap’ moments.

I’m sure you disagree with my rankings, but let me know on social what your ranks are and why: @Andrew_Rotondi