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Regular season success in the Bronx hasn’t translated to the postseason

The Yankees have won the second-most games in the majors since 2009, the year of their last title, but have yet to win it all again. What gives?

2009 World Series GM 6 - Philadelphia Phillies v New York Yankees
It’s been 13 seasons since the Yankees last emerged victorious in the Fall Classic, their third-longest drought in team history.
Photo by Focus on Sport/Getty Images

After their defeat at the hands of the Astros this October, the Yankees’ current pennant drought reached 13 years, taking sole possession of third place for them all-time. It also marked their fourth-longest stretch without winning a World Series title. Yet, what differentiates this period from other dry spells is that it has coincided with a good deal of winning. But is there something different about the Yankees’ winning lately that has spurred the drought?

Since the Yankees last hoisted the trophy in 2009, they’ve emerged victorious in 57.1 percent of their regular season matchups, trailing only the Dodgers at 58.8 percent. However, they’ve only won 100 games twice, which ties them with the Rays (if you count Tampa Bay’s extrapolated 2020 performance) for third place in the majors. The Astros and Dodgers have four 100-win seasons apiece — five for the latter if you count what their 2020 season was on pace for.

While the Yankees have put up winning records every season since they thrashed the Phillies in a six-game series over 13 years ago, their distribution of wins per season has been rather narrow. Their nadir, 84-win seasons in 2014 and 2016, lies just 19 wins below their peak of 103 in 2019. The Dodgers have a 31-game spread between their best (111 wins) and worst (80 wins) seasons during that same time frame; the Astros and their early-2010s futility make for a 56-game spread. This is good for the Yankees in the sense that they’ve never hit rock bottom, but on the other hand, they’ve rarely seemed like the pride of their league.

Further, the Bombers’ median wins per season during the drought (including their extrapolated record from 2020) has been 92, matching their mean wins exactly. This indicates that the Yankees’ distribution of wins is not only narrow but approximately normal; there is no tail of a few really great seasons (which would pull the mean higher than the median) or tail of a few really poor seasons (which would pull the mean below the median). The Dodgers have a mean four games higher than their median, while the Astros have a mean two games lower.

With an ever-expanding postseason, and the playoffs still a crapshoot, the Yankees’ tactic might be a winning strategy: just make it to October as often as possible, and let the coin flips decide the rest. No lengthy rebuilds a la the 2010s Astros, no all-out blitz like the 2020 or 2022 Dodgers (though of course the Yankees have been in their own version of win-now mode for quite some time).

Sure enough, in the article linked above, this strategy has worked for the Yankees if we study the playoffs from 1995-2022 — they’ve overperformed their Pythagorean record (based on run-scoring differential) more than any other team in the playoffs since then. But a lot of that success is likely due to the club’s late-90s run. Since FanGraphs began tracking World Series odds in 2014, the Yankees have failed to win a title despite running up 0.63 expected ones by pre-playoff odds; they’ve never won a pennant despite running up 1.21 expected ones.

Yankees’ Pre-Playoff Odds (% Chance)

Year WS Odds Pennant Odds
Year WS Odds Pennant Odds
2022 10.0 24.7
2021 7.5 14.1
2020 9.1 18.4
2019 16.2 25.9
2018 9.2 14.6
2017 6.5 12.3
2016 0.0 0.0
2015 4.5 11.0
2014 0.0 0.0
Sum 63.0 121.0
Data via FanGraphs. Odds taken day prior to the beginning of postseason each year.

The Astros, and a series of other AL clubs, have stood in their way. The Yankees’ best year during this stretch, 2019, coincided with that of the Astros — while the Yanks had a 25.9 percent shot at the pennant and a 16.2 percent shot at the World Series, the Astros had marks of 46.6 percent and 35.2 percent, respectively. Those two marks were higher than the Yankees have put up in any season since 2014, and the Astros’ World Series odds that year make up more than half of the Yankees' cumulative odds since 2014. The other time the Yanks had at least 10 percent odds, this past year, the Astros had better prognostications too, and they knocked the Bombers out of the playoffs again.

There’s something to be said for the Yankees’ ability to field competitive teams year in and year out. But it might not be the best way to secure another recently-elusive World Series victory — just one year of an Astros-esque 35.2 percent odds team is worth more than three 10 percent odds teams. Though the Astros didn’t win the series that year, in 2019, they at least snagged the pennant. Their win in 2022 also coincided with best-in-the-majors World Series odds at 17.2 percent, higher than the Yankees have ever been since FanGraphs began tracking them.

Realistically, the best way for the Yankees to reach those heights is for them to continue investing in both free agents and player development. Thankfully, the next dynasty could be on the way, with Anthony Volpe and Oswald Peraza likely to begin playing big (or bigger) roles this year, joining the now-locked-up Aaron Judge, Gerrit Cole, and Carlos Rodón. Not to mention, with the Red Sox looking shaky and the Orioles failing to make significant offseason moves, the Yankees could run away with the division again and bypass the volatile Wild Card Round, which alone would boost their title odds tremendously. Who knows, 2023 just might bring number 28.