I never bothered to get an example, but the rubber stamp might be a sort of autograph.
At one point in the late 70's early 80's he was at Fenway a lot, special batting coach? Something like that.
For autograph hunters, he would ask for a donation to the Jimmy Fund, and if someone declined but still insisted on a signature he'd go for the rubber stamp he carried.
I think he was a bit less mercenary with kids, and generally the amount he wanted was small anyway, like $5 or 10?
Now the question is if its that rubber stamp, or some other one.
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