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Julie Vognaralways see me coming! I'd have to say the 1882 Providence Grays Harper's Woodcut with Wrights, Radbourn and Ward which i won on e-bay for $14.95 from an art gallery that had stuff going way back to the 1700s. And a couple of years ago, i think at Purdey's Pleasanton show (now defunct), I got a 1947 Jackie Robinson Bond Bread (that's from the set of 13 Robinsons, not the set of lots of major stars) for $100, in ex-mint. Some dealers set up without knowing what they have on their tables!
I was sent a big box of '68 and '69 Topps, free, but that's part of a very sad story, so I'm not counting it.