The New York publishing establishment, for its part, viewed the success of Roth’s Ulysses with something closer to a covetous leer. Throughout the late 1920s, many of the most prominent publishing houses had flirted with or seriously explored the possibility of coming to terms with Joyce and of braving the prosecution that would likely if not inevitably follow publication of the most infamously obscene book in ancient or modern literature. But even publishers with the stomach for litigation were unwilling to stomach the noxious financial terms demanded by the resolute Beach, to whom Joyce had assigned control over the Ulysses rights—or perhaps it was simply that the gentlemen publishers of that time were too sexist to negotiate with a woman. Interest among the major houses faded away, and as the 1930s began, the US market remained wide open for exploitation by Roth, who was widely rumored to be preparing a second unlicensed edition. Joyce, contemplating from the photophobic gloom of his latest fugitive Paris apartment the prospect of never making a dime from the work that had cost him his eyesight, his health, and eight years of his life, felt his own financial resolve begin to weaken.
Two erudite, polished, and well-connected New York hustlers caught wind—or maybe it was simply an intuition, a canny surmise—of this wavering, and saw in it, as hustlers so often do in the face of weakness, an opportunity. One of these bon vivants was Bennett Cerf, then in his early thirties. Eight years earlier, Cerf had ditched a career in his Alsatian Jewish father’s Harlem lithography business, using $25,000 inherited from his tobacco-heiress mother to buy himself a partnership in the celebrated New York publishing firm of Boni and Liveright. Eager, savvy, impulsive, and, like any good hustler, trusting implicitly in his own judgment, Cerf seized on his new partner Horace Liveright’s financial straits to cut a deal and buy him out of the Modern Library, an imprint that Cerf astutely recognized as the hidden jewel of Boni and Liveright.
The books on the Modern Library’s list of “modern classics” tended to have gone out of print or to have entered the public domain, which made them cheap to publishers and affordable to readers, even in the thick of the Great Depression. Building on the Modern Library’s success, Cerf and Donald Klopfer, his boyhood friend and business partner, expanded into publishing new work by contemporary authors, chosen “at random,” under the sobriquet of Random House. But if Random House were going to compete with the big houses, it needed a big hit. It needed to make a literary splash. It needed, Cerf decided, the dirtiest, most indecent, obscene thing ever written. He knew—publishers had known for years—that if you could somehow contrive to get around the obscenity problem, you could sell a million, or at least several hundred thousand, of the damn thing.