Whenever Harold Loeb entered the boxing ring with Ernest Hemingway, Loeb worried that his younger, heavier friend would beat the crap out of him. It was 1924 in Paris, and though the two expat writers were on good terms, Loeb remembered watching Hemingway pummel their acquaintance Paul Fisher. So Loeb relied on a mix of strategy and trust: strategy, by noticing that Hemingway’s eyes signaled his next punch; trust, by hoping that his friend wouldn’t give him a bruising. He was lucky enough to be spared, at least until Hemingway wrote his first novel, The Sun Also Rises (1926), in which Loeb turned into a foolishly romantic, toxically awkward Jew named Robert Cohn. “The book hit like an uppercut,” Loeb would confess near the end of his life.

The irony—and the clue that signaled Hemingway’s punch—was that The Sun Also Rises depicts Robert Cohn as an expert boxer, a former champion at Princeton who took up the sport to counteract his Jewish self-consciousness. Initially friends with the Hemingway-esque narrator, Jake Barnes, Cohn falls in love with the charming Lady Brett, runs off with Brett to the coast and then whimpers after her at the bullfighting festival in Spain, where Barnes’ cohort mocks and abuses him. (“Take that sad Jewish face away,” Brett’s fiancé shouts at Cohn.) In a climactic scene, Cohn punches Jake Barnes to the ground and runs weeping to his room. He’s not an easy character to like.

And yet I’ve always been fond of Robert Cohn precisely because he’s a clumsy romantic, a Jewish Quixote with his head in the clouds and his feet in a WASP’s nest. As Ruth Wisse has pointed out, Cohn possesses all the traits of a schlemiel, the dreaming, blundering fool from Yiddish folklore whose weakness spins comically into a type of strength. But instead of finding humor in Cohn’s shortcomings, Hemingway ridicules his deviation from the heroic standards of bullfighters and brave men. I wanted justice for Cohn; I wanted his side of the story. So imagine my thrill when I discovered that in 1959 Harold Loeb had published a memoir combatively titled The Way It Was. I rushed to the New York Public Library to put in a call number, eager to see the minor character defend his honor. The Jew Strikes Back was my imagined subtitle for the book. What I found was much funnier. The author of The Way It Was sounded like … Robert Cohn.

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To be sure, Loeb had a lot more substance than Cohn, but they do nearly rhyme. Loeb was also a social blunderer, a reader of fanciful travelogues and an incurable romantic. In his life, he demonstrated an extraordinary knack for becoming infatuated—with ideas, with projects, with people. The Way It Was is a catalog of sky-high dreaming and inevitable failure. Loeb was a rare type in Jewish history, not a fake schlemiel so much as a schlemiel cut off from his Jewish roots, who was saved nevertheless by the force of his self-delusion.

Loeb devotes only a few pages in The Way It Was to his family, which, like Cohn’s, was one of the wealthiest in New York. His father died when he was young and his relationship with his mother, the daughter of Meyer Guggenheim, receives scant mention beyond her nervous breakdown. Loeb emerged from a cold, sheltered upbringing without confidence or direction, and after graduating from Princeton, he slummed it on a ranch in Alberta, then married and started a bookstore called The Sunwise Turn. (Throughout his life Loeb displayed an anti-talent for giving titles: His novels were called Doodab, The Professors Like Vodka, and The Tumbling Mustard.) In 1921 he left his wife and kids and moved to Paris to start an international magazine, Broom, which was his passport to the higher spheres of 1920s culture. He hung out with so many famous artists that The Way It Was can read more like an itinerary than a memoir, as he speeds through his run-ins with Wallace Stevens or Picasso, his chess game with Duchamp and his dinner with James Joyce, who to Loeb’s annoyance only wanted to talk about French provincial cooking.

Loeb fell hardest for Hemingway, who, with a boyish smile and patched-up jacket, represented Loeb’s American masculine ideal: “I admired his combination of toughness and sensitiveness, his love of sport and his dedication to writing. I had long suspected that one reason for the scarcity of good writers in the United States was the popular impression … that artists were not quite virile.” In contrast, Loeb’s girlfriend at the time, the fashion correspondent Kitty Cannell, sized up Hemingway as a fraud, playing “the part of a ruthless, hairy-chested, unintellectual he-man in order to suppress his compassion.” It was Loeb’s own fears about being “not quite virile” that led him to idolize the exact person likely to change into his betrayer, as if he sought out those with the power to crush him.

Loeb also fell for women, continually: first Cannell, who “was matter-of-fact and understanding” about Loeb’s sexual shyness, and later Duff Twysden, the model for Brett in The Sun Also Rises. Like Brett, Duff had a reputation for charm, boldness, and carousing. Loeb’s account of their love affair is painfully funny. Duff’s laugh, Loeb writes, “had the liquid quality of the lilt of a mockingbird singing to the moon,” whatever that sounds like, and at night “she moved around in a muck of lost souls without losing a certain aloof splendor.” After Loeb’s performance anxiety mars their first tryst in Paris, the pair absconds for the French coast. With his first novel on the way and Duff at his side, Loeb enters his paradise, and yet his behavior there serves as an unintentional guide in what not to do on an amorous getaway.

Within a day of arriving at the pension in St. Jean de Luz, Loeb announces that he’s falling in love. “Careful, darling,” Duff replies as they walk on the beach, “let’s not confuse ourselves.” At dinner when Duff shows him her sketchbook (Hemingway left this talent out of his portrait of the soused-up Brett), Loeb runs upstairs to bring down his essay in Broom called “The Mysticism of Money,” which Duff finds uninspiring. Even with a lover in paradise, Loeb can’t get out of his head. On one of their last nights, Duff proposes a ritual:

“In Scotland when the Black Watch drink a toast, they throw their glasses against the wall so that no one will ever drink from them again. … To us! May we see each other always as we do tonight!”

She hurled her glass into the darkness. I heard it shatter against the stone wall.

I drank and threw my glasses with all my strength after hers. It hit a branch and deflected. We heard the thud as it dropped to the ground.

A dog barked in the distance. I wondered if it had been barking before. I shivered.

Ooof. What’s heartbreaking about this scene, which is worthy of the Marx Brothers or Woody Allen or Seinfeld, is that Loeb doesn’t find it funny. Instead of laughing at himself, the poor guy shivers, like he’s the hero in a romance novel in which every mishap wounds his honor. He lacked the cultural awareness to make a joke out of his transcendent klutziness, stranded between a Yiddish folklore he didn’t know and an American-Jewish clowning yet to emerge, cursed to live in a gentile world without the sword and shield of Jewish humor. Loeb’s inability to view himself as a schlemiel made him, in a darkly humorous way, even more of a schlemiel.

It’s after Duff returns to Paris, with Loeb remaining behind on the coast, that I began to see what Hemingway changed in the novel, where Cohn and Loeb broke apart. In The Sun Also Rises Cohn travels to Spain against everyone’s wishes, but Loeb suggests that he was following orders. He quotes a letter from Duff expressing her love (soon to be revoked) and another from Hemingway encouraging him to join them abroad. It’s as if Hemingway scripted a disaster between his friends, stage managing it so that Loeb’s starry-eyed devotion would crash into Duff’s sleazy fiancé, Mike (in the novel) or Pat (in life). And the bullfighting festival was a disaster for Loeb as well as Cohn. Loeb hated the cruelty of bullfighting but withstood all the bigoted mockery out of the desperate hope of rekindling his passion with Duff. In fiction and in life, Cohn/Loeb’s willingness to walk through shame in pursuit of female intimacy is hard to stomach.

Loeb was a rare type in Jewish history, not a fake schlemiel so much as a schlemiel cut off from his Jewish roots, who was saved nevertheless by the force of his self-delusion.

Even worse, Loeb didn’t punch his friend. In The Way It Was, after Loeb calls out Hemingway for insulting him and they search for a place to spar, Loeb worries out loud that his glasses will get smashed. Hemingway jokes that he should hold them; they smile and agree on a ceasefire, and the next morning Hemingway leaves an apology, wishing Loeb “so long and good luck.” No punches were thrown.

But of course, the punch only waited for fiction. In The Sun Also Rises, Jake Barnes feels “unforgivingly jealous” that Cohn ran off with Brett, and Hemingway felt the same about Loeb’s affair with Duff Twysden. Barnes is impotent, Hemingway had a wife, but the sexual resentment of a Jewish peer—and the longing for the unattainable woman, Brett/Duff—reverberates. The whole expat community in Paris knew that Cohn echoed Loeb, and so by crafting a scene in which a pathetic Cohn slugs Jake Barnes, Hemingway both invented a dramatic confrontation and quite literally plotted revenge.

Disappointingly, The Way It Was refuses to punch back. It ends in 1925 only a few months after the bullfighting festival, with Loeb sad about losing Duff but reassured that, “The thing between us had been wondrous.” There may be a link between the book’s silence on The Sun Also Rises and its suppression of any reference to Jews, as if by acknowledging the former he’d be forced to discus the latter. Early in their friendship, Loeb takes Hemingway to see Leon Fleischman, a publisher who offered to pass along Hemingway’s first story collection. After leaving the meeting, an ungrateful Hemingway calls Fleischman what Loeb reproduces as “the low ______.” We can infer from Kitty Cannell’s reaction that “______” is a slur, but Loeb defends Hemingway’s right “to express himself violently.” The word “Jew” never appears, and yet through the book Loeb feels devastatingly alone, at one point asking himself: “What was it in me that set me apart?” It’s peculiar. Can Loeb really not fathom why he’s an outsider?

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It’s also peculiar that Loeb scrubs any trace of Jewishness from his memoir because when The Sun Also Rises came out in 1926, he was working on a novel where desire and Jewish identity collide with astonishing perversity. The main character and authorial stand-in of The Professors Like Vodka (1927) is John Mercado, a staid American professor who visits Paris with a colleague in search of adventure. At a Russian cabaret he falls instantly in love with the childlike prettiness and muscular hands of an émigré named Cléopâtre. After a few nights together, he and Cléopâtre go to a club where two black women are dancing together. Mercado scoffs at them, and Cléopâtre misinterprets his homophobia as racism. Embarrassed, Mercado counters, “I have often heard that you Russians hate the Jews,” to which Cléopâtre replies with one of the more shocking boasts in literary history:

“Jews!” she said, and looked dreamily at the polished thumbnail on her left hand. “But they’re not people.”

“I’ve killed many Jews,” she added agreeably.

Well, that changes things! In the afterword to The Professors Like Vodka, Loeb confirms the real-life basis of Cléopâtre, as well as his fascination with “her large, powerful hands that could crush mine.” She rode with her father during the 1917 Revolution and, after rampaging through a village, would embrace tied-up Jews with a dagger between her breasts. Even if Cléopâtre exaggerated or Loeb misremembered, there’s a pattern in his attraction to ferocity, whether it was Duff Twysden’s brash love or Hemingway’s taste for “express[ing] himself violently,” since violence—even violent expression—is what the sensitive, self-doubting, “not quite virile” Loeb can neither voice nor possess.

Still, the infatuation with a Jew-killer takes him into new territory, and Loeb’s avatar, Mercado, flies through every reaction you can imagine. In the moment he’s shocked and appalled; later he’s amused. Then he undergoes a metamorphosis, casting off his small, anxious self and swelling with Jewish pride after years of repression: “The teacher of English faded into air. In his place stood a proud arrogant man who gloried in emotions that would have horrified his former self. He felt himself growing bigger and bigger … he lived.” He pictures himself next to King David and Saul, a member of a “warrior race” who will wreak divine vengeance on Cléopâtre the Canaanite. In the next moment, he desires the blue-eyed girl with powerful hands “more than his life.” In the next he feels lonely and disgusted with himself. Here at last is a dilemma that Loeb’s overactive brain cannot process, a knot in his soul where his two greatest needs—for female intimacy and for Jewish identity—pinch together in mysterious ways.

Mercado continues the affair with the goal of revealing his Jewishness and jolting her out of prejudice. He’s smitten not only with Cléopâtre but with the drama of the situation: “It seemed glorious to combine man’s love of a woman, symbolic hate of a racial enemy, and fear, fear of the unknown.” Glorious? But on second thought sleeping with the enemy is kind of glorious, which is why it’s an enduring theme in Jewish art from the “Palestinian Chicken” episode of Curb Your Enthusiasm, to Heinrich Heine’s poem “Donna Clara,” to The Book of Esther. It captures the ultimate Jewish fantasy, a chemical reaction in which desire for the Other synergizes with fear that the Other wants to kill you. Cléopâtre’s appeal is that she lets Mercado feel so grandly, idiosyncratically Jewish while he tries to get laid.

Finally, after pages of courtship and then a night of lovemaking, Mercado fesses up. If there’s something terrifying about Mercado’s Jew-engorged change into “a proud arrogant man,” then Cléopâtre’s transformation goes in reverse. Hysterical, she bares her chest, offers Mercado a dagger—her Jew-killing dagger!—and begs to be stabbed. Then she collapses into a childish stupor. Bigotry, when exposed, disorients the bigot even more than the victim. And now that he’s fulfilled his mission, Mercado shrinks back to his former size: nervous, cerebral and, in a final encounter with Cléopâtre, unable to stand up for himself. After a brief stint as a warrior Jew and “proud arrogant man,” Mercado returns to his life as an unwitting schlemiel.

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Given Loeb’s penchant for grand visions and his newfound identity as a Jew, it’s hardly a surprise that in the late 1920s he fell for Zionism, especially the idealism of the kibbutz. He spent a few months in a guesthouse in Jerusalem and took a road trip around the north with his then-girlfriend, future-wife Nicky, who, on a later trip to the Far East, Loeb caught fooling around with a member of the French Foreign Legion. After the Great Depression, and still supported by his independent wealth, Loeb returned to the United States and wrote a nonfiction tract that envisions society as a technocratic utopia dedicated to art. He became a government economist and was now titling his books The Chart of Plenty: A Study of America’s Product Capacity Based on the Findings of the National Survey of Potential Product Capacity. During World War II his utopian ideas about technocracy lead the House Un-American Activities Committee to declare him “a crackpot.” Loeb’s work as a technocrat didn’t so much mark the decline of his youthful romanticism as its successful conversion: from literature to lovers to Zionism to social engineering. Twice more he married. He died in Morocco in 1974, at age 83, still a wanderer.

After registering his experience in The Way It Was in 1959, Loeb must have felt a burden off his chest—that is, until A.E. Hotchner published his credulous, adoring Papa Hemingway in 1966. In Hotchner’s book, Hemingway alleges that after reading The Sun Also Rises, Loeb put out word that he wanted to kill Hemingway and that Hemingway waited for him in the same bar for three days, but Loeb chickened out. To this falsehood, Loeb lashed out with an essay titled “Hemingway’s Bitterness,” in which he finally stopped being polite. He fights dirty, wielding rumors and hearsay. He diagnoses Hemingway with paranoia, PTSD from WWI, and gender anxiety brought on by his mother’s habit of dressing him in girls’ clothing. He mocks the idea that Hemingway was ever poor. Though still defensive about anti-Semitism, he unbleeps Hemingway’s slur of the publisher Leon Fleischman: “That damned kike.” Anger rises off the page, and one can detect how powerless and ashamed Loeb must have felt upon seeing himself reflected in the warped mirror of Cohn. “Nothing in our relationship,” Loeb writes with cathartic honesty, “justified the distortion of the real friend that I was into the Robert Cohn of The Sun Also Rises.”

I searched for Hemingway’s response to Loeb’s essay, but couldn’t find it. After a while I realized the obvious. “Hemingway’s Bitterness” was written in 1967, six years after Hemingway, an old, booze-soaked Nobel laureate, alienated from his friends and with no one left to betray, shot himself in the head.

“Man’s tendency to desert reality for romantic figments is the cause of nearly all his troubles,” Loeb writes in The Professors Like Vodka, and while it’s true that Loeb’s dreaming got him in trouble, it’s also what saved him. In the boxing match with Hemingway, Loeb never stood a chance, but he possessed a durable romanticism that weathered shame, betrayal, loneliness, prejudice, cuckoldry, and self-inflicted clumsiness. It was Hemingway who wrote, “All sentimental people are betrayed so many times.” Hemingway meant it with grim fatalism, as the eternal torment of a soft heart, one that may have applied to his own self-destructive romanticism. In contrast, the story of Harold Loeb, who outlived Hemingway by 20 years, calls up a tragicomic vision in which perpetual betrayal requires perpetual hope, and the schlemiel, knocked to the dust, rises again with his dream broken but his dream-making intact.

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