A dear friend of mine is an attorney with deep admiration for a Chief Justice John Roberts. Is it a pipe dream to think I could ask him for a personalized autograph for my friend? If not, how would I even go about making such a request?
Unfortunately Chief Justice John Roberts does not sign autographs at all. The only time he does is for official documents. I have never heard of anyone successfully getting his authentic autograph through the mail and only once have I heard of a successful in person situation (and they had connections). You probably can’t even buy one right now they are so rare. Once in a blue moon one (a rare in person that someone with connections got) will come up for auction but they go for minimum $500.
The ones you see obtained through the mail are all autopen (machine signed), likely sent out in the first year or so he was Chief Justice. Even these are rare to get nowadays. I have not heard of anyone even getting a response of any kind from Roberts in years.