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I have never seen the Yankees win in-person (but I still have hope)

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After dropping a series to the Orioles in excruciating fashion, we could all use a little laugh. Here’s a short story of my own personal agony that will (hopefully) provide a bit of relief.

MLB: Baltimore Orioles at New York Yankees Wendell Cruz-USA TODAY Sports

As a kid growing up just outside Toronto, the only time I got to see the Yankees play live was when they were in town to play the Jays. In 29 years of cheering for the New York Yankees, though, I have never seen them win a game in-person. Over the years, I’ve seen some downright bizarre stuff happen to this team. Whether I’m the physical embodiment of a bad luck charm or this is just some bizarre coincidence remains to be seen, but I’ve gained a greater sense of optimism when it comes to the Yankees because of this personal losing streak. I’m going to tell you three quick stories, and then tell you why I’m choosing to remain positive.

September 2009: The Good (Depending on Who You Ask)

The Yankees were in town and I was sitting down the third baseline hoping for a foul ball and a Yankees win. The only issue? Roy Halladay, Yankee killer, was pitching.

Against one of the deepest lineups in the league, Halladay threw a complete game one-hitter on 111 pitches, striking out nine. With the division all but locked up already it wasn’t a meaningful loss in any way, but Halladay’s performance is still, to this day, the best pitching performance I’ve ever seen in-person. This game acts as a reminder that, at the age of 17, I still hadn’t been in the stands to see a Yankees victory. And I still hadn’t caught a foul ball.

September 2016: The Bad

Luis Severino, the highly-touted prospect I’d been following for some time, was set to make his first start in Toronto.

For those of you not from Toronto, it’s somewhat of a tradition to pre-drink at one of the many overcrowded, overpriced bars along Front Street before heading to the Sky Dome Rogers Centre. Unfortunately, I spent a little too much time at the bar that day and missed the entire first inning and top half of the second. Realizing how much time (and money) I’d wasted, I sprinted down the street to the ballpark.

Sweaty, out of breath, and trying to find my section, the crowd suddenly erupted and I heard some random dude yell, “FIGHT!” Everyone in the concourse area swarmed to the railings to watch a full-on bench-clearing brawl. It turns out that a number of hitters were thrown at, and Severino had retaliated by hitting Justin Smoak. Severino, naturally, was thrown out of the game... before I got to see him throw a single pitch.

Those with encyclopedic knowledge of the Yankees are probably saying, But Jesse, the Yankees came back in the 9th and won that game! Yup, they did. But I wasn’t there to see it. One of my pre-game drinks didn’t sit particularly well with me, so I took off for the hour-long train ride home in the 7th. When the Yankees were losing 3-1.

September 2010: The Downright Cruel

I decided to take my girlfriend of two months to her first baseball game. There are three things you need to know before we go any further: (1) I was a massive fan of Alex Rodriguez; (2) I’ve never caught a home run or foul ball; and (3) she hates baseball. We were sitting in my favorite seats—a few rows up in left field—and everything was going well.

After a few innings, boredom kicked in and she started to get a little restless. I gave in and, after the fifth inning, decided I’d show her around the concourse level for a bit. After a few minutes of walking around, I heard an extremely loud crack of the bat followed by an even louder chorus of boos. The Rogers Centre has these little TVs littered all around the stadium that show a slightly delayed broadcast, so I rushed over to see what happened and, to my horror, A-Rod had hit a home run. The ball landed just a few seats away from where we were sitting. Oh, and the Yankees lost that game 8-4. We’re getting married in October, though, so I guess it wasn’t a total loss.

September 2021: Why should you care?

Every time I have seen the Yankees play live, it has been a performance filled with on-field mistakes and missed opportunities. That sounds a little familiar, doesn’t it? But these disappointments have led me to become an eternal optimist—one day, I will catch a foul ball and I will see them win. I just have to remain positive.

To make a long story short (too late), what I’m trying to say is this: as Yankees fans, we’re conditioned to have a championship-or-bust mentality because, well, for a really long time, that was the reality. Because of this, it’s easier for us (myself, the eternal optimist, included!) to get bogged down in the negatives than it is for fans of any other franchise in this sport. But, in the same way that I keep going to Yankees games in-person hoping to see a victory despite knowing that history is stacked against me, we should try to remain at least somewhat optimistic.

I think we can all agree that this isn’t the season we were expecting in April. Between injuries and poor on-field performances, I think those of you who are feeling overwhelmingly negative are justified in feeling that way, especially after the recent series loss to the Orioles. After all, I’m about one or two more double plays or blown saves away from ripping out my hair, so I’m right there with you.

Yet, despite all of the struggles and heartbreaking losses, the Yankees are still (just barely) leading the Wild Card race and FiveThirtyEight gives them an 86% chance of making the postseason—by far the highest of all non-division leaders in the AL. If only they could swap places with the Mets... So, it’s not all bad, is it?

I guess this is my roundabout way of saying that, despite the hair-pulling awfulness of this season, I still have hope for the 2021 season, and you should, too. Am I being wildly optimistic for no good reason? Given the latest series against Baltimore, yeah, probably. But it’s at least a bit more fun than the alternative. After all, if I can continue showing up to games after 20+ years of seeing them lose, then surely we can handle the final 26 games of the season... right?

*This has been adapted from my original Pinstripe Alley writer application in anticipation of a major series against the Toronto Blue Jays. (At least we don’t have to see Robbie Ray?)