Philip Roth was a notorious author of the extraordinary stories in Goodbye, Columbus, and novels Letting Go, When She Was Good, and Portnoy's Complaint. Jay Cantor wrote two remarkable novels in the period between 1970 and 2000: The Death of Che Guevara and Krazy Kat and a little later published Great Neck. This chapter groups together the writers: Sontag, Auster, Cantor, Price and Lethem because they are Jewish American writers who do not advertise their Jewishness in any particular way. In Chabon's novel it is something like a smothered dream and permitting oneself the fantasy of freedom is a route to whatever freedom is to be had. In this perspective, to live a Jewish life in the American language is to remember difference and loss with especial intensity and to be alert to the chances of slipping free from at least some of the restrictive chains of the New World.