Chapter One

1637–1912

Many skeletons in family closet,” Leander Wapshot wrote in his diary. “Dark secrets, mostly carnal.” Even at the height of his success, Cheever never quite lost the fear that he’d “end up cold, alone, dishonored, forgotten by [his] children, an old man approaching death without a companion.” This, he sensed, was the fate of his “accursed” family—or at least of its men, who for three generations (at least) had seemed “bound to a drunken and tragic destiny.” There was his paternal grandfather, Aaron, rumored to have committed suicide in a bleak furnished room on Charles Street in Boston, a disgrace too awful to mention. One night, as a young man, Cheever had sat by a fire drinking whiskey with his father, Frederick, while a nor’easter raged outside. “We were swapping dirty stories,” he recalled; “the feeling was intimate, and I felt that this was the time when I could bring up the subject. ‘Father, would you tell me something about your father?’ ‘No!’ And that was that.” By then Cheever’s father was also poor and forsaken, living alone in an old family farmhouse on the South Shore, his only friend “a half-wit who lived up the road.” As for Cheever’s brother, he too would become drunken and poor, spending his last days in a subsidized retirement village in Scituate. No wonder Cheever sometimes felt an affinity to characters in Ibsen’s Ghosts.

Despite such ignominy, Cheever took pride in his fine old family name, and when he wasn’t making light of the matter, he took pains to impress this on his children. “Remembe...