They both had residences in New York City and Palm Beach. Kennedy had a family estate in Palm Beach, along with an apartment in the Carlyle on Manhattan’s Upper East Side. Trump has Mar-a-Lago and Trump Tower.
They both had aviator older brothers who died. JFK’s older brother, Joseph P. Kennedy Jr., was killed in action flying a bomber in World War II. Trump’s older brother Freddy, a professional airline pilot, died in 1981, an alcoholic.
They both had wealthy fathers in the real estate business. JFK’s father made money as a stock market player, Hollywood movie investor and liquor importer. But one of his biggest long-term investments was in real estate, Chicago’s Merchandise Mart. Trump’s father was also in the real estate business. Like JFK, Donald Trump has been underestimated as a born-rich heir.
Both were elected by narrow margins. Kennedy won 303 electoral votes in 1960; it looks like Trump will have 306. Kennedy won the popular vote in 1960 by only a minuscule margin; Trump lost the popular vote in 2016 to Hillary Clinton.