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Posted By: Dan Bretta

The guy second from left is probably Tom Daly who was a coach with the Red Sox throughout the 1930s and 40s.

edited to add: probably not an old timers game as this is pretty clearly Spring Training in Sarasota looking at the grandstands. The picture is a shot of the Red Sox coaching staff.

edited a second time to add: I would almost bet it's spring training 1939.