On this day in 2009, the Yankees won their 27th and most recent World Series title. How has it been 16 years already? Goodness. They’ve been back to playoffs in 12 of the 16 seasons since then but have only been back to the Fall Classic once—last year, when they folded against the Dodgers.
The 2009 title also remains the Yankees’ only championship since the three-peat dynasty died while seeking a fourth in Arizona during Game 7 of the 2001 World Series. So that’s one title in 25 years, and that quarter-century
basically represents my entire diehard fandom since I didn’t really like baseball until just before becoming a teenager. It’s more than most teams can say, but when the Yankees themselves go all-in on “CHAMPIONSHIP OR BUST,” they only have themselves to blame for setting everyone up for disappointment.
Nonetheless, the warm memories of ‘09 will never fade. I’ll always remember where I was when A.J. spun his Game 2 gem, when Damon stole two bases on one play, when A-Rod continued his torrid postseason with a go-ahead hit in Philly, when Godzilla clobbered six RBI off Pedro in the clincher, and of course when Mo clinched it. Of course it’s easy to remember for me as well because I was stuck in college in the middle of Pennsylvania without much personal spare change, so the obvious answer for the majority is: sitting on my ass in my sophomore year room and watching on TV, putting off my multivariable calculus and linear algebra assignments while occasionally lurking in the Pinstripe Alley comments section (yes, this is my origin with the site). No regrets, babyyyyy.
These are moments frozen in time, and given the scarcity of championships in my own personal fandom, I really miss the feeling. Seriously, I sometimes well up just looking at Hideki Matsui. As long as the Yankees remain in the dance, they’ll have a shot—and as 2023 recently demonstrated, that’s no given—but they have yet to have it all click again like it did during that magical year. Sigh.
Today on the site, Peter will consider starting pitching as a Yankees offseason priority, Nolan will review the fourth week of Arizona Fall League play, and Jeremy will grade newcomer closer David Bednar’s 2025.
Questions/Prompts:
1. Where were you when the Yankees won it all in ‘09? We’ve probably done this before, but hell, let’s do it again.
2. Even acknowledging that the Cowboys are still “THE DALLAS COWBOYS” to network execs*, how uninteresting was the selected Monday Night Football matchup yesterday? (Arizona Cardinals vs. Dallas Cowboys)
*Aside: Remember the 2000s mock stereotype of “Yankees/Cowboys/Lakers” frontrunner fan? Feels long-dead, no? Maybe it’s easy for me to say because I rolled my eyes at it, as I was never a fan of the other two and indeed still actively mock Jerry Jones.












