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Tom's memory goes back to 1943, where as a child, he wishes he could for once spend Christmas with his parents as opposed to his Aunt Elizabeth and butler James. Unfortunately, Tom's hopes are dashed when he receives $1,200 and the grim news that his parents are going to San Fransisco. All George seems to pay attention to is the amount of money Tom received, this missing the whole point of the story.
George's memory takes us to 1941, where George's unemployed father desperately seeks work. George is his optimistic self, predicting his cleaning store business and making an I.O.U. of all the things he plans to buy his parents when his ship comes in. Incidentally, George's father doesn't get the job, but has a merry Christmas with George anyway. James Avery, best known as Uncle Phil on The Fresh Prince of Bel-Air, makes a cameo appearance as the landlord whom the elder Jefferson stands up to, in typical Jefferson fashion, withholding rent in exchange for better maintenance. Tom points out that at least George's father was there for him, despite not having anything, leading to a toast to their friendship.
When Louise and the gang return from caroling, they find Tom & George asleep on the sofa, observing they'll "never know the real meaning of Christmas".
George's story takes place in 1941, even though earlier episodes suggest his father died in 1939, when he was 9 years old.