IN HER CLASSIC STORY “Envy,” Cynthia Ozick drew an unforgettable portrait of the miseries of Yiddish writers in America—ignored, untranslated, cut off from both the dead past and the indifferent future. Edelshtein, the obscure poet who is the story’s hero, is constantly going on diatribes against the next generation of American Jews, with their indifference to Yiddish: “What right had these boys to spit out the Yiddish that had bred them, and only for the sake of Western Civilization?”

Reading this fascinating new book, I kept wondering if Edelshtein knew how good he really had it. For if the world of American Yiddish writing was small and beleaguered, the world of American Hebrew writing that Weingrad describes was practically non-existent. During World War I, Weingrad points out, “the Yiddish daily press in the United States reached a peak circulation … of more than six hundred thousand,” whereas Hadoar, the leading Hebrew periodical in America, “had a circulation of about nine thousand to twelve thousand.” By the end of World War II, the number of important Hebrew writers in America could be counted on the fingers of one hand; when the last of them, the poet Gabriel Preil, died in 1993, “the story of the immigrant Hebraists and the literature they created in America came to an end.” In fact, at the end of Weingrad’s book, he reveals that Ozick knew that story very well: her own uncle, Abraham Regelson, was a Hebrew poet, and the bickering Yiddishists of “Envy” are at least partly based on “the immigrant Hebraist writers.”

For Weingrad, it is precisely the marginality, even the perversity, of the American Hebraist project that makes it so immensely interesting. “The simple and obvious fact is that despite their best efforts, the Hebraists were always a marginal group that never succeeded in determining the values of the American Jewish mainstream.” This is not surprising when you consider that Hebraism as an ideology was born in Eastern Europe, where the conditions of Jewish life and literature were totally different than in the United States.

In late nineteenth-century Russia, a ferocious battle was fought between supporters of Yiddish and supporters of Hebrew as the language of Jewish national revival. The choice had profound social and political implications. Yiddish, as the actual spoken language of the Jewish masses, attracted the support of socialists and populists. Hebrew, the language of the Jewish classics, tended to appeal to Jews who had received and rebelled against an elite religious education—which explains why the literature of Haskalah, the Jewish Enlightenment, was mostly written in Hebrew. At the same time, Zionists embraced Hebrew as the language spoken by Jews in Palestine, while anti-Zionists preferred Yiddish as the language of the Diaspora.

This ideological division crossed the Atlantic along with millions of Eastern European Jewish immigrants in the years between 1880 and 1920. Yet the Yiddish-Hebrew debate quickly became obsolete in America, where the younger generation leaped happily into the open arms of English, leaving both ancestral languages behind. The sheer mass of Yiddish-speaking immigrants ensured that Yiddish literature and journalism would thrive for a few generations, until its native speakers died out. But the idea of creating a national Hebrew literature in America could not appear other than quixotic—especially since there was an actual Hebrew-speaking society growing in Palestine and then Israel. To be an American Hebraist meant rejecting the language of America, while also refusing to leave it.

This double-bind resulted in a literature that was constantly preoccupied by its own futility. American Hebrew writers, Weingrad writes in his first chapter, were extremely caustic about American life, especially American Jewish life: “their writings frequently castigate American Jews for their ignorance of Judaism, their materialism and coarseness, and their assimilatory values.” In the Old World, the Hebraists may have been champions of secularism and foes of religious tradition, but in the New, complained Menahem Mendel Dolitzky, there was “no one to fight against, no one to fight with, and nothing to fight for.” Dolitzky began to miss his old Hasidic opponents: “They were at least loyal and devout Jews. Here we have a pack of boors, ignoramuses, whose only thought is to ‘make a living,’ with nothing spiritual about them.”

The Hebraists’ distaste for America was clear from the way they wrote about New York, where most of them lived. The poet Shimon Ginzburg, who came to America in 1912 at the age of 22, wrote about the city in phantasmagorical terms. In “Bamigdal” (“In the Tower”), he describes the Statue of Liberty holding up not a torch but “a clenched fist,” and telling new arrivals, “Come to me, all who are hungry. … Die here of hunger like a stray dog.” At moments, as Weingrad nicely points out, Ginzburg foreshadows his more famous namesake, Allen Ginsberg: like the author of “Howl,” he sees the city as a “Moloch,” eating immigrants alive. Another poem, “Behar beit Kolombiyah” (“On the Temple Mount of Columbia”), is set at Columbia University, where Ginzburg attended Teachers College. Here the poet marvels at the city’s ethnic diversity—“up the marble stairs hurries a daughter of Calcutta;/ and after her, a Japanese, a Negro,/ a young man from Jaffa in Judea, and myself”—while feeling humiliated by its opulence: “You have conquered me, you the rich and I the poor.”

For an antidote to everything they hated about New York, the Hebrew writers turned to rural America and to an idealized Native American past. Some of the most touching works Weingrad discusses feature the Jewish writer exploring the Gentile countryside, and being surprised by the kindness and hospitality of Americans. “Misis Voods” (“Mrs. Woods”), a poem by Hillel Bavli, channels the voice of a 92-year-old farm widow, who explains: “a Catholic church, a Baptist/ or Presbyterian, or Hebrew,/ I don’t discriminate between one sect and another,/ between people I don’t make distinctions.” Sometimes, this openness itself could look like a threat. In his autobiographical novel Ele toldot adam, translated under the terrible title In the Grip of Cross-Currents, Ephraim Lisitzky writes about falling in love with a Canadian Gentile named Becky, while living in a small town in Ontario. He must make an effort to tear himself away from the “simplicity and uprightness” of “these non-Jews among whom I lived,” to reclaim his Jewish and Hebraist identity.

But the single unlikeliest episode in the history of American Hebrew writing must be the vogue for epic poems about American Indians, on the model of Longfellow’s “Hiawatha.” Weingrad explains that writing about Indians allowed the Hebraists to claim an authentic American subject while avoiding, and implicitly criticizing, modern urban America. The image of the Indian as bearer of an endangered culture also had an instinctive appeal to these writers, struggling to preserve their own ancient heritage. All these elements can be seen in Benjamin Nahum Silkiner’s 1,500-line poem Mul ohel Timurah (“Before the Tent of Timmura”), whose publication in 1910 marked “the beginnings of an estimable Hebrew literature in the United States.” Weingrad summarizes the complicated plot, showing how the “the Indian was a dark mirror in which the poet could contemplate the most extreme Jewish hopes and fears,” including the dread of extinction.

One does not come away from Weingrad’s chapter on these Indian epics (titled “Going Native”) with any urgent desire to read them. But there are a number of works discussed in American Hebrew Literature that sound fascinating and might add a new dimension to our sense of American Jewish writing. Some of them have been translated into English, like the poems of Gabriel Preil, which Weingrad writes about with obvious affection: “The medievals had their wine, the Romantics their opium; for Preil, the cafes of New York were the launching pad for his reclusive sensibility, their windows his eyes on the world.” But most have never been translated, including Shimon Halkin’s Ad mashber (“To the Point of Crisis” or “Until the Crash”), which Weingrad describes as both a “Great American Novel” and “a precursor to the novels of Yehoshua and Yaakov Shabtai.” “This is America!” muses one character in the book; “If it weren’t for Jews and Judaism, you couldn’t find a nicer place in the world than this great wide land, eager to live and in love with life.”

It was the American Hebrew writers’ realization that the Jewish world they longed for could never exist in America that led most of them, finally, to emigrate to Israel. Halkin himself decided as early as 1929 that “I could no longer believe at all in the naïve dream of our Hebrew-cultural renaissance in exile,” that the Jews “could not exist as a historical people except in one place, the Land of Israel.” More than eighty years later, American Jews do still exist as some kind of a people; but Weingrad’s book is an often haunting reminder of the path we did not take.

This piece was originally published in Tablet.

Adam Kirsch is a senior editor at The New Republic.