I wouldn't exactly say that all their losses have been "chokes". The Yankees problems post-2000 have boiled down to one thing, and that is pitching. Every big name pitcher they have accquired since then has been a bust (right up until the time they get rid of them, at least). Pettite and Clemens seemed average, and the Yanks screwed up resigning one and lost both. And Clemens has one Cy Young after that, and if his team could've gotten him any support would've had another this year. And Pettite is now a healthy pitcher that would be an ace for any number of teams, and will probably help the Astros beat the team that had this year's best record. They dumped Contreras and El Duque this year, both of which had solid years for the White Sox. And they spurned David Wells, who was solid for Boston and has always been a big game pitcher. But they picked up Randy Johnson, expecting a performance like last year (where he should have won the Cy Young) and instead got an average performance. Kevin Brown never panned out for them, and neither did Leiter or the parade of other one-year too late pitchers they tried to get. And the younger pitchers they tried to get seemed to wither in New York (Vasquez, Weaver, Pavano). Basically, that cost the Yankees probably 2 titles. Despite some of the high priced players not doing well in the playoffs, it was poor pitching that cost them.
And I also think that they made a big mistake not getting Vlad Guerrero. Sheffield has been all they asked for and more, but they could've easily found a spot for Vlad, or just not have signed Sheffield. One will be an MVP candidate for 3-4 more years, one will be a candidate for the next 10-12.
But the best thing about the Yankees is that they will be back next year, and they will threaten again. Although I'm not really sure if there's any free agent pitching that is ace quality (maybe Schmidt? Millwood?).
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