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JFK was only in the White House for less than three years, but man, did a lot go on during that time. You can read all about it here.
In 1963, he visited West Berlin and gave his famed "Ich bin ein Berliner" speech ("I am a Berliner"), which demonstrated the U.S.'s solidarity with West Germany and led to mass applause among the 450,000 in attendance. It's this speech that Reagan is referencing in the first part of his own speech, when he tells his own audience that he always has a suitcase in Berlin.