Been thinking about this one a lot since I first read the thread. From my collecting lens, which focuses on Red Sox cards, I'd run with the following:
C: 1972 Topps Carlton Fisk (get the bonus of two other players for the team)
1B: 1938 Goudey Heads-Up Jimmy Foxx (MVP season with the Red Sox)
2B: 1960 Topps Carl Yastrzemski (listed as a 2B on it, so it counts for this exercise)
SS: 1952 Topps Johnny Pesky (part for the player, part about the set)
3B: 1985 Donruss Wade Boggs (because it captures his relentlessness in watching the pitch all the way to the catcher)
LF: 1939 Play Ball Ted Williams (because of course)
CF: T206 Tris Speaker (with a rare back)
RF: 1973 O-Pee-Chee Dwight Evans (I've got a soft spot for OPC cards, what can I say?)
P: 1916 M101-4 Babe Ruth (because of course)
Three backups:
DH: 2013 Topps SP variation David Ortiz giving his famous speech - iconic moment of an icon
P: 1984 Fleer Update Roger Clemens
P: E90-1 Cy Young
It was a fun exercise, and I know I left off some good players/cards. I own some of them, but would love to own them all!
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