Sinatra: The Chairman by James Kaplan review – a 360-degree portrait

Four marriages, countless affairs, links with the mob ... volume two of a landmark biography finds the singer’s later life at odds with his art

For a reminder of the best and worst of Frank Sinatra, look no further than the recording of a concert he gave at Carnegie Hall in the spring of 1974, shortly after emerging, at the age of 58, from a brief “retirement”. A medley of three ballads – “Last Night When We Were Young”, “Violets for Your Furs” and “Here’s That Rainy Day” – is prefaced by a clumsy, cheesy, self-regarding monologue drawing the sort of sycophantic laughter and applause to which he had long become accustomed. Then he gets down to the business of bringing a great seriousness to bear on the trilogy of peerless songs, each an established part of his repertoire, reaffirming all the qualities of technique and interpretation that had made him the greatest male interpreter of Broadway melodies.

This dissonance between the life and the art, a permanent feature of the singer’s career, is a biographer’s dream and the inevitable preoccupation of the concluding volume of James Kaplan’s massive two-part study of Sinatra. The music’s sublime artistry provides a counterpoint to the lurid details of four marriages, countless affairs and fist fights and a web of connections with America’s ruling elites, from the back rooms of mob-run casinos to the White House, all spanning a period of great cultural upheaval.

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