Dear Diary, the Yankees’ early exit from the playoffs this year was infuriating. Thinking about why this is so, it is because the team is squandering, or has squandered, three golden opportunities. These are opportunities every other baseball team would want. Losing when you have them is almost a sin. This is why this season’s pathetic defeat hurts so much.
The three golden opportunities are that the Yankees had the best pitching staff in baseball this season. Then, there are also the twin questions of peak Gerrit Cole and peak Aaron Judge. Cole might have been the best pitcher on the planet. He is still good, but he is not even the best pitcher on his own team. Judge, the Yankee Captain, was the most feared hitter on the planet, but he missed half the regular season and all 5 playoff games. Do you think these missed opportunities make this season’s defeat particularly bitter?
Diary of a Yankees Fan #3

Pitching
Diary, it is probably not even questionable that the Yankees had, on paper, the best pitching staff in baseball this season. That they lost early is a waste. They had a fearsome starting pitching rotation of Cam Schlittler, Gerrit Cole, Max Fried, Carlos Rodon, and Will Warren. They also had starting pitchers Ryan Weathers, Clarke Schmidt, and Ivan Nova. To boot, the team had the best earned run average of all bullpens in baseball.
We are told, diary, that winning baseball games is about pitching and defense. This is because if the opposing team cannot score, they cannot win. The Yankees played poor defense this season, and it hurt them in the first inning of the second game against the Rays. A team must also score runs. For long stretches this season, the Yankees failed to score, including in the division series against the Rays. When you cannot score, and your defense is porous, it does not matter how good your pitching is; you will lose.
Peak Gerrit Cole
When the Yankees signed Gerrit Cole after the 2019 season, he was the best starting pitcher on the planet. He is not that anymore. He just turned 36 (on September 8), and he is coming off reconstructive elbow surgery, probably a diary-worthy event. He missed all of last season, and the first couple of months of this season. When he came back, he was up and down, though he was throwing hard.
Did the Yankees take advantage of the best years of this outstanding starting pitcher? No. Cole pitched well in the regular season, and even won a Cy Young Award (in 2023), but he pitched in the World Series only once. In the 2024 World Series, he made a costly error. The error was so bad that he failed to cover first base on a ground ball fielded by the first baseman. A diary-worthy event, if there was ever one. So, Cole just turned 36. If the 2027 season is canceled, in 2028 he will be 37. He has already had one major injury, and time is undefeated.
Peak Aaron Judge
Time is also affecting the slugger Aaron Judge. He is not as young as you might think. He turned 34 in April. That means that if the 2027 season is cancelled due to the lockout, he will not play again until he is 36 years old. He might have one or two more good seasons left in him. However, he will probably never hit 60 home runs again. Remember, he, too, is coming off a major injury. Then, diary, he got hurt again. He must have been very hurt, because he missed all 5 of the playoff games this year.
Did the Yankees take advantage of having this imposing slugger at his peak? No. Instead, he has been noted for his lack of postseason success, and he was not even in there this postseason. He just looked sad watching the Rays celebrate on the field at Yankee Stadium. He is at risk of becoming the best baseball player to never win a World Series. That would be a diary-worthy event!
Conclusion
The Yankees, in getting swept by the Rays, failed to take advantage of three golden opportunities. There is considerable uncertainty about whether next season is going to happen. However, when the baseball players get back to the field, they will have good pitching. They have a lot of work to do on their lineup and should build in redundancy to compensate for the inevitable injuries to the aging Cole and Judge.
Don't stop here
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