The worst was not buying a Rosen find Mantle for 3k because I had a nice one that would later grade 6. Second would not buying a Plank and Magie for 10k that were in the 5-6 range. Both in the mid-eighties. Another bad one was not buying a LeBron Exquisite RPA. I was bidding on them when they were under 2k and kept getting out bid. Now a 200 k+ card.
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