Casey Stengel and Dave Roberts...

[BobC]

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.

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.