So busy was Podhoretz's literary life after retiring from the editorship at Commentary – five books and, every year, four or five essays – that he might have seemed to lack the leisure for anything else. And it is true that, compared with the strenuous socializing and child-rearing of the early years, his and Midge's routine quieted down. The days of Family partying in New York were long over, their neoconservative friends were scattered around the country, and in any event the Podhoretzes were of an age when the occasional dinner party or conference gathering satisfied their gregarious appetite. They preferred the visits of Rachel, Naomi, and their families from Washington, Ruthie and her children from Israel, and John, now in his forties, happily married and with two children, from the Upper West Side.

Such visits typically occurred in East Hampton, where the Podhoretzes spent much of the summer and early fall. Not far away was Roger Hertog, an investment specialist whom Podhoretz had come to know when helping raise money for Moynihan's Senate campaigns in 1976 and 1982. Sometime around the latter year Podhoretz asked whether Hertog would be willing to manage the roughly $25,000 he had been able to set aside – not realizing that Hertog's firm, Sanford C. Bernstein & Co. (now AllianceBernstein), commonly took on portfolios starting at a quarter-million. “I told him I'd be honored,” Hertog would remember, recognizing it as an opportunity to aid one of the most prominent literary intellectuals of his time.