That wasn't the "greatest generation". They were still in their teens and twenties in 1937. It was their parents and grandparents who were running the country back then. The generation which won the Second World War was the generation that went on to get rid of segregation.
When Democrats needed Southern votes they courted the South with stuff like this stamp. There were still people around whose parents had survived the Civil War and the government had to make them happy. It's a different country now.