A Tale of Two Cities, or, My Hat Story


29May2016, Chicago IL. Five years ago, I took a 3-day weekend trip to my favorite city, with my daughter Natalia, to visit my friend Bruce. We did a few of my favorite things: lunch at Pizzeria Dué; visiting the Art Institute of Chicago; walking the Navy Pier at night.

On this day, we took in a ballgame at historic Wrigley Field, where the hometown Cubbies were taking on my Philadelphia Phillies. On a beautiful Spring day, we witnessed one of the worst baseball games I’ve ever seen. Both the Phillies and the Cubs took turns trying to lose this game, and in the end my Phils prevailed, losing 7-2.

Before we left the stadium, I decided to buy a Cubs cap. I had seen somebody else in the stands sporting a cool powder-blue lid, with the old-fashioned cubby logo on the front and, most importantly, the flag of Chicago embroidered on the side. I’ve always loved this flag! When I found this hat at a concession stand, I was taken aback by the price: $41. I had never spent this much money for a baseball cap before. Now I have. This beauty is now mine.

A funny thing happened later that year: the Chicago Cubs won the World Series. For the first time in 108 years.

23May2017, Houston TX. Another year, another baseball game in another city. This time, I was in Houston for business with our sales team, and we decided to take in an Astros game. In a relatively uneventful game, the home team defeated the visiting Detroit Tigers, 6-2.

Before the game started, after we had loaded up on beers and ballpark food, I decided to visit a concession stand and find a cool cap. I was already sporting a retro Astros t-shirt, and I was long a fan of the old rainbow-themed jerseys, so the perfect hat found me: a black Astros cap with a rainbow brim. I bought it, and it cost me a helluva lot less than $41!

A funny thing happened later that year: the Houston Astros won the World Series. For the first time ever, which was 55 years as a baseball franchise.

So, twice in two years, the same thing happened. I attend a game in a different city, buy the home team’s hat at the stadium, that team goes on to win the game that day and the championship that year. Strange, huh?

As this story started getting around, my friends and coworkers started bugging me to come to their towns, attend a game there, buy a hat in their stadium, so their team could win a championship. Cleveland. Milwaukee. New York. The requests came pouring in, and suddenly I felt this strange sense of power. But where should I try next?

04Nov2018, Baltimore MD. This year I was attending a football game at M&T Stadium, home of the Baltimore Ravens. We were in the Constellation Suite, where I was entertaining some customers and prospects along with my Constellation coworkers and their guests. It was first class all the way, with local craft beers and tasty crab cakes to beat the band!

I wasn’t planning this, but I decided to buy a Ravens hat at the stadium. It took me a while and several concession stands before I finally found the perfect purple lid. Sadly, this cap wasn’t actually perfect, as it didn’t have the Maryland flag anywhere on it, which is another of my favorite flags. So I bought a team pin with the flag logo in it and permanently attached it to the side.

Sadly, the Ravens lost that day to their arch-rivals, the Pittsburgh Steelers, 23-16. My customers were happy, as they are Steelers fans and brought their Terrible Towel to prove it. My prospects, who are Ravens fans, were not amused, but we all still had a good time. I, of course, had to represent my Philadelphia Eagles by wearing my Chuck Badnarik 60 jersey. As a Ravens fan who saw me in the stadium said, “typical Eagles fan, wearing that jersey to a Ravens-Steelers game!”

A not-so-funny thing happened later that year: the Baltimore Ravens did not win the Super Bowl. They made it to the playoffs, losing in the first round to the San Diego Chargers, 23-17.

My hat streak was over.

How did this happen? Was it because I switched from baseball to football? Was it because the home team lost that day? Was it because I drove to the game instead of flying there? Was it because the hat I bought was missing one of the elements I was looking for in a cap? Who knows?

All three of the home teams in question were on the rise, but only the first two made it all the way to the top. Both the Cubs and the Astros overcame extremely long championship droughts, while the Ravens had won two Super Bowls in the past 20 years. I guess it just wasn’t their time. And my time was up.

I haven’t bought a cap at a sporting event since. I did buy a 50th anniversary jersey at a Philadelphia Flyers game a few years back, but that doesn’t count. The Flyers are my absolute favorite sports team, and they haven’t won a championship in 46 years, so they’re long overdue. I guess I need to buy a new Flyers cap at the Wells Fargo center soon…

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