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Come Fan with UsSunday, August 9, 2026

11 More Ugly MLB-Licensed Caps

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I hope you won’t think I’m exaggerating when I tell you that several people requested a sequel to last week’s “Top 20 Ugliest Caps Licensed by Major League Baseball.” I’m talking mid-single digits!

“But I can’t go back to the well so soon,” I told my bosses. “I’ve got to zig when the audience expects me to zag!” In the end, though, I acquiesced to their threats entirely reasonable demands. So here you go, you jackals! Will you never be sated?

"I laughed so hard, beer was coming out of my nose!" -anthropomorphic beer keg

Perfect if you already have camouflage hair.

They even made it smell like a disgusting old cap!

The only kind of cap they let you wear in Heaven. Bought a dozen in anticipation of last weekend's Rapture... imagine how disappointed I am we're not all dead.

I wanna go fast!

This is how we do it in Back Bay, y'all! [gang sign]

In my younger and more vulnerable years, my father gave me this Red Sox "Gatsby" cap.

A nice contrast to Detroit's tasteful, understated on-field cap.

This is called the "Intruder" cap, probably because of its suspected role in a number of recent home invasions.

Rumors that this hat is made entirely out of dolphin skin are probably unfounded.

Brings back fond memories of malaise and stagflation.

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