A 1952 Topps grey back for $1 or $2 circa 2002. Got it from a big dealer I bought a lot from as a kid, just picking through low grade commons I didn't have. I did not realize for several years until I put my master set checklist together that it was a special card.
I got a 1964 Philadelphia Jim Brown for $1 a few years ago from a baseball dealer. It was in his random dollar box of vintage. I pulled it out and told him it looked like he had a card in the wrong box, and he looked at me like I was an idiot and said no, he did it right. So I just bought it for $1. Apparently he did not know literally any of the football stars.
This year I got a 1954 Johnston Cookies Bob Thompson (the SP card) in EX-MTy range for $5 in a bargain bin at my local show. Found a bargain for a lower grade one on eBay later, so I will put the nice one in my trade bait box. Seller also had a 1961 Bazooka Jim Perry for $1, which isn't a very valuable card or anything but it was really cool to pickup for a buck.
I have gotten better bargains, but not from a dealer at a show. On eBay circa 2005, I found a horrifically listed lot in the wrong category with none of the words one might look for, with a T206 3 Finger Brown, a T205 Old Mill SL miscut, and 3 T220 silver borders. Won it for less than $10 shipped when nobody else bid, and still have all the cards. I won a bunch of uncut panels of T220 proof cards for under $100 each, listed wrongly as reprints. I got the panel with 8 Mike Donovan proofs for $90 - that card has only 5 extant production copies known and the last two went for in between $2K and $5K. I messaged the seller to discuss the sheets, and he replied with "just bid", so I did. Probably never going to beat that. Just picked up a T219 Red Cross Jeffries for $30, that was nice. Worth about ~$300.
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