Cities & Towns

The Cubbies Hat You'll Cherish Forever

A Windy City keepsake is a son’s nostalgia trip.

Words by Jacob WheelerIllustration by Janice Wu



22 May 2024

Reading Time

4 Minutes

AS WE WALKED TOWARD the marquee gate at Wrigley Field, my dad knelt down and pulled the baseball cap out of a mud puddle. On its corduroy front, “Chicago Cubs” was embroidered in a loopy cursive. He smiled, shifted a giant bag of peanuts into his left hand and waved the cap around with his right, like he’d found a good luck omen.

He had. That rainy April day in 1989, the Cubbies beat the reigning World Series champion Los Angeles Dodgers 1-0. Sitting along the first baseline, bundled in our winter jackets, my dad, sister and I watched Greg Maddux, the Cubs’ young phenom, pitch a 9-inning shutout and score the game’s only run. Afterward, star first baseman Mark Grace signed my scorecard as I stood on my tiptoes alongside the players’ parking-lot fence. Back at our hotel, I narrated the game’s highlights to every stranger in the elevator.

The restaurant Greek Islands has anchored the 'hood since 1971. The saganaki—fried kasseri cheese in a flaming skillet—is as Chicago as a dog dragged through the garden.

The magical afternoon sparked our family’s annual baseball pilgrimage. Every summer until I left for college, my dad and I drove from rural Northern Michigan, deep in the woods of Leelanau County, to the Windy City, where we saw ballgames, ate Greektown feasts and caught plays at the Chicago Shakespeare Theater. The road trips cemented a father-son bond—and year after year, my dad wore that cap. He’s 72 now. Still loves the Cubbies. And the hat still hangs on a coat rack next to the front door.

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