Chaperoned by his parents after just becoming a teenager, James Fiorentino took an artist's leap of faith by bringing a prized Joe DiMaggio painting he had done of the legendary Yankee great to an autograph show that DiMaggio was appearing at.
Fiorentino reminisced: "He was always tough at these things and usually didn't sign artwork. He looked at me and said, 'Oh my gosh! Did you do this?' I guess for him to even say something was kind of a big reaction. He seemed to like it and autographed it for me.
Source: http://mlbforlife.com