Texasguitarslinger wrote "The oldest pick I own is actually my Mom's pick from when she played guitar in high school in the '70s. I think it's a Fender medium, but the logo's worn off. It's lasted about thirty years longer than the guitar did. My uncle smashed it trying to impersonate metal bands in the 80's."
Ouch!
I've got an old pick that B.B.King handed to me after a concert in 1971, but I'm no longer sure which one it is out of a bunch of old picks that I have lying around
But, since I now use only my fingers, my oldest guitar picks date from 1946!!!

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......it's a topsy-turvy world when noses run and feet smell...

I have a Mosrite Ventures one--don't remember where I got it from, but it's old.

I do still have a couple I used back in high school, as far as ones I've had the longest, but that Ventures one has to be older than that.

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It wasn't Willy-Nilly, it was at crows.

I don't understand how people lose picks... I never do. I bought my first electric guitar in 1979, and bought a pick to go with it. I used that single pick for about 20 years until it was worn down and I had to retire it. (Still have it.) I always had a small baggie with other picks, but that's the one I used.