After learning that his new girlfriend Lois works for high school classmate Duncan Meyer, Jerry tells Elaine of their longstanding dispute over an inadvertent head start in a race, one which crowned Jerry as the school's fastest runner. Meanwhile, after her argument with a Chinese restaurant deliveryman, George finds evidence that Elaine's new boyfriend is a Communist. As Elaine confronts Ned, George answers a personals ad from a Communist Party newspaper. And, unaware that his secretary Ada is listening, he claims to be a longtime Communist in order to get a date. Then, after Kramer is hired as a department store Santa Claus, Ned's observations, about the working conditions cause him to think twice about the job.
When George drops by during lunch and pretends they haven't seen each other in years, he tells Duncan and Lois that Jerry won the race fair and square. However, as George uses the opportunity to portray himself as a millionaire, Jerry is goaded into running the race again. With many old classmates coming to see the rematch, Jerry decides not to run. But, Duncan's threat to fire Lois forces him to reconsider. Meanwhile, Elaine's lying gets Ned banned by the Chinese restaurant, too, while Kramer's Communist propaganda costs him and his elf their jobs.
Asked to answer the charge that he is a Communist, George suddenly finds himself being sent to Havana to sign baseball players for the Yankees. At the race, Jerry mistakes a car's backfire for the starter's gun. As a result, his healthy head stan allows him to win once again. Finally, George discovers some eerie parallels between Fidel Castro and Yankee owner George Steinbrenner.