The flags on Debbie's (Stephanie Steele) bike have 50 stars. The episode was set in 1956, when there were still only 48 states.
That's director Jerry Paris as a heckler in his first of four uncredited appearances as a supporting character.
This episode takes place the week of November 6, 1956.
The title is based on Theodore H. White's "The Making of the President" series of books.
Wendell Willkie was the 1940 Republican presidential nominee who opposed (and lost to) FDR. He is most known for his interventionist policies, proposing the US enter WWII (Pearl Harbor, which eventually led the US to enter the war, wouldn't happen until December 1941).