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The Warm Unexpectedness of Nostalgia

It sneaks up on you.

Will Leitch
8 min readMar 19, 2025

While walking around Gainbridge Fieldhouse at a halftime break during the Big Ten Tournament here in Indianapolis, I ran into a man named Jay, and his college-aged son. Jay looked vaguely familiar to me, like I’d known him in some sort of previous life, but I’m also getting older now and honestly a lot of people are starting to look like that.

“Will!” he said, shaking my hand. He was dressed in all orange, just like I was, the Illini game started in 20 minutes, all six Leitch men in attendance were wearing orange, we’re not monsters. “It’s Jay! I haven’t seen you in years!”

My mind scanned through the internal rolodex, Columbo piecing together the clues. Jay … Illini shirt … college-age kid … that voice is familiar … why do I get the sensation, when I hear that voice, like I’ve heard it coming up from behind me? … maybe I sat in front of him on the school bus?

“This guy,” Jay said, nudging his son and pointing his thumb toward me, “this guy was the funniest catcher in the entire baseball league. He’d just make jokes the whole game. Some guys wanted to hit him with their bat, but most of them thought it was hilarious.”

Right! Jay!

The reason Jay’s voiced sounded familiar coming from behind me is because he was the primary…

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Will Leitch
Will Leitch

Written by Will Leitch

Author seven books, including “How Lucky” "The Time Has Come" and "Lloyd McNeil's Last Ride." NYMag/MLB. Founder Deadspin. https://williamfleitch.substack.com

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