August 26, 2004. Myrtle Beach, South Carolina. My brother bought two hats at a store during a buy-one, get-one 50% off promotion. For my birthday, he gave me a bright blue, unstructured Chicago Cubs cap from Twins Enterprises.

It was just what I was looking for.

Since I started fly fishing, I had worn a number of hats. The guys on Saturday mornings wore hats, so I knew that I needed to as well. Early pictures of me on the river show a mixed bag of sports teams and conventional tackle hats. In the photo of me holding my very first trout on the fly, I’m sporting a black and gold Zebco Rhino hat. Flat billed and high crowned in 1998, I was cool before cool was cool.

As I became more steeped in the culture of fly fishing, I realized that any old hat would not do. I had to spend more money to wear something that made a statement. Obviously. I went to Orvis and bought a super-drab, tan and olive hat with a brook trout stitched on the front. The bill was a little long and the metal clasp on the back started to turn the back of my head green after a few months, but it was a legit fly fishing hat. I wore this all throughout high school and into college. It got gross from sweat, creek water, and whatever chemicals come off frosted tips. It was the 90’s, after all.

Then in college, I began to do some sales for a small fly rod company. They sent me a hat, and I felt obligated to wear it. I had sold out, and I knew it. My head was a billboard. Honestly, I doubt any of the rods I sold came as direct result of someone looking at my headwear and making a decision to buy an expensive fishing pole. It was a dark period for hats.

Around this time, the super-nasty, beat to a pulp, scratched brim, dumpster hat was a thing among college guys. And guess what I was. One could walk into a Lids and buy a pre-scuffed hat, but that was the do not pass go, do not collect $200 poseur move. I wanted that hat, but I wanted it on my terms.

But what hat would I choose to grow in and with? I mean, this hat would accompany me on every fly fishing trip I’d take for the foreseeable future. It would be on my head for hikes, trips to the grocery store, and any time that shampooing/brushing was simply too much to ask. This was a big choice.

Then my birthday came, and I was holding a Cubs hat that fit perfectly. It was soft, it was comfortable, and it was going to be the hat.

Growing up in Chicago, I had rooted for the Cubs pretty hard. Baseball was my sport, and the Cubs were my team. We’d take a number of trips into the city to watch them at Wrigley every year. The afternoon start times allowed me to catch the fourth inning on when I got home from school.

But they lost. And lost. And lost some more.

For the purposes of my hat selection, this was perfect. You see, I get upset with my sports teams. I have a standing policy that I won’t wear a Chicago Bears shirt for at least three days after a loss. It is my silent way of protesting their poor performance. I’m sure that when I do it, they hear about it somehow and put in extra practice in order to avoid future shaming.

This was perfect, because the Cubs always lose. I could wear the hat the same day of a 10-0 shutout on the tail end of a seven game losing skid and not care. People would see me and respect me for my headwear and unspoken longsuffering. It was a match made in baseball purgatory.

So I began wearing the hat. I’ve got pictures of me in my Cubs hat with trout, steelhead, bass, and pickerel. Fishing, hiking, out on the town. New England, the Mid Atlantic, and out West. Sometimes forwards, sometimes backwards (I’m still on the front edge of cool).

And it went from bright royal, to dull blue, to grayish. I began, largely at the behest of my wife, to clean the hat. I renovated a house in the hat, which led to some interesting stains and scratches. Wearing it out on the town was less acceptable. But it still was my go-to hat.

Then, a few years ago, I started having to do some repairs. The fabric was separating from the bill, and I used flexible head cement to keep it together. If I held my hat up to the light, I could see through it like it was dingy sheer curtains. I knew that its time was short.

I ordered a new hat in anticipation of the day. It was a 47 Brand Chicago Bears cap. Football had supplanted baseball as my spectator sport of choice, and I liked the idea of wearing orange to reduce my chances of getting shot.

On August 26, 2014, I wore my new hat for the first time and retired my Cubs hat.

This past week, the Chicago Cubs won the World Series. For the first time in 108 years, they weren’t losers. They were winners for the first time in my life… for the first time in my grandmother’s life. Sports have the auxiliary effect of bridging decades and circumstances, and their victory got me thinking. I thought about my childhood fervor, my recent renewed interest, and my beat-up old Cubs hat.

It was a good hat, as any fishing hat should be. It blocked the sun, always fit right, and even served to identify me on the streams that I frequented. 10 years of wearing a hat isn’t anything like a century-plus of waiting for a championship. But a lot happened in those 10 years.

I’m glad I’ve saved it. I don’t know how much use it will get from here on out. But it is a trophy that witnessed the catching of fish that could be trophies. It was on my head as my wife and I were on dozens of mountain peaks across New Hampshire. It was the passive observer of my life as I passively rooted for the Cubs for a decade of mediocrity.

It is just a hat, but it was the hat I needed.