Anyhow: Would Sinatra sing (and vote) for Trump were he alive? Unquestionably.
The son of a Hoboken Democratic fixer, Sinatra campaigned for FDR, naturally—but was also one of millions who made the leap from left to right when Reagan ran. Whether or not his defection was philosophically motivated, or reflected his desire to remain in the orbit of power, even his closest associates or most insightful biographers aren’t entirely certain. Another chapter in the life of Francis Albert Enigma.
But consider the evidence: Here are two paradigmatic New Yorkers who brawled their way to the top; tabloid liaisons here, a trio of devoted children there; men of eye-watering generosity (you’ve heard the “we’ve paid off your mortgage” story by now) and spleen (the name of Sinatra’s record company, Reprise, was pronounced with a long “i,” as in “reprisal”).
Note, too, the almost belligerent philo-Semitism: In 1948, as a favor to a stranger he met in a bar, Sinatra couriered a million dollars cash to a ship full of arms earmarked for Israel, docked at a New York pier; Trump, dead set on making Mar-a-Lago nonrestricted, taunted Palm Beach’s town council by sending them copies of Guess Who’s Coming to Dinner.
