I am a Cub guy also and collect virtually anything Cubs. I have Cub cards from early on to today although the ones from 1990 on I got mainly from trading. I think the most fun I have is finding an odd ball I don't have. I like and enjoy the early Cub cards (pre-1940) but don't go out of my way to get them. I try and find something I need in various auctions and, usually, bid what I would pay for them as I don't have deep pockets. To me having fun going after Cub items (not just cards) I want is most important whether I get them or not. I am always amazed at how much early stuff is out there and, many times, I just like to look.
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