Harmon Killebrew and Monte Irvin were signing machines. Their stuff is very affordable. Rollie Fingers, Gaylord Perry are a couple more baseball that quickly come to mind, even though they both charge a very small fee generally to sign. It is generally pretty comparable to what their items would go for on the market.
Going back to the Hockey post regarding holy grail Hockey signatures, I would have to venture a guess that since were are dealing with the big world event right now that there would be some interest in finding a signature of "Bad Joe" Hall who was a legend in the early days of Hockey who succumbed to the Spanish Flu during the infamous Spanish Flu Epidemic a little over 100 years ago.
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