Depends on the setting. Most living HOFers are accessible through signings, but if you're talking about your chances of getting them to sign for free in an in-person setting, there are a few tough guys.
Jim Rice is an absolute miserable human being and would probably be close to the top of my list. Roberto Alomar, if you're trying to get him on a HOF specific item, will simply not do it. He charges a premium for HOF items at signings, and for free he will flatly refuse to sign the HOF inscription, HOF plaque postcards, etc.
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