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Originally Posted by Casey2296
I'm just guessing but I think Stengel probably has the longest span of baseball cards from his 1910 T210 to his 1965 Topps card.
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Just off the top of my head, what about Connie Mack? Appeared in the 1887 - 1889 Old Judge issue, followed by various issues throughout the years. He eventually even had his own designated issue of cards in 1951 with the Topps' Connie Mack All-Stars. He was in the 1961 Fleer Baseball Greats series, 1963 Bazooka All-Time Greats cards, and has appeared in other issues and sets over the years since then as well.