Jesus?
Seriously, in Sports it would be Joss I am sure. The Kelly was expensive but it was also an absolutely beautiful signed albumem photo inside a program so part of the price was due to the medium it was signed on. My guess is that if a Joss signed document ever surfaced it would top $200,000. In the political world Gwinnett is tops but I think there are like 50-60 of his that exist, the demand is just so high. Shakespeare would probably top $10,000,000 but I don't think any are in public hands (all in museums or legal courthouses).
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