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I'm pretty confident this is the Henry Grimes Healey and the picture was taken in 1959. Grimes lived in Alexandria, VA and he raced the Healey at nearby tracks such as Marlboro in Maryland and Virginia International Raceway. Did some more searching and couldn't come up with anything else on him that would give some clue as to who is shown in the picture. The picture isn't very clear and doesn't show the person's face very well. He bears a resemblance to a young Robert Redford but I couldn't find anything to link Redford to the races that Grimes entered the Healey. Redford was living in New York in 1959 and beginning his acting career. Here's a 1959 picture of Redford:

It's just a wild guess. Please get back to us with the answer once the quiz is completed.

It's just a wild guess. Please get back to us with the answer once the quiz is completed.