To the small but influential group of his American admirers, Trotsky appeared as a kind of Soviet Garibaldi or George Washington, fighting for freedom against an evil empire. The problem, as Robert Service shows in his new biography Trotsky, is that Trotsky himself was one of the men chiefly responsible for that evil. In the October Revolution of 1917, he was second only to Lenin in leading the Bolshevik coup to success. In the years of civil war that followed, Trotsky, as commissar for the Red Army, designed the campaigns that inflicted horrific suffering on the civilian population of Russia, Poland, and Ukraine. None of the Soviet leaders outdid him in zeal for collectivization and terror, or in his commitment to spreading the Communist revolution across Europe and the world. Service, one of the leading historians of the Soviet Union and the author of biographies of Lenin and Stalin, sums up his verdict on Trotsky this way: “He was close to Stalin in intentions and practice. He was no more likely than Stalin to create a society of humanitarian socialism.… He reveled in terror.”

How, then, did Trotsky become a symbol, to some of the most intelligent American leftists, of a more humane and democratic Communism? In part, as Service writes (and the Farrell essay demonstrates), it was because of “their naivety. They were blind to Trotsky’s contempt for their values…. Like spectators at a zoo, they felt sorry for a wounded beast.” But for the Jewish intellectuals who clustered around Partisan Review, he was an especially irresistible figure, since Trotsky himself was the most powerful Jewish intellectual who ever lived. While this part of Trotsky’s legacy is incidental to Service’s book, it is a significant chapter in the political history of American Jews, and Trotsky helps explain both the allure and the danger of the mass murderer who was affectionately known to his followers as “the Old Man.”

He was born in 1879 as Leiba Bronstein—the name Trotsky was a nom de guerre, like Lenin (Vladimir Ulyanov) and Stalin (Iosif Dzugashvili). Bronstein’s parents, unusually for Jews in the Russian Empire, were farmers; they belonged to a colony of Polish Jews who had settled in the Ukraine, as part of a czarist project for dispersing and assimilating the Jewish population. As Service shows at the beginning of his book, this meant that Bronstein “did not have a life associated mainly with fellow Jews.” His parents were not devout, and Leiba was sent to a Lutheran German school in Odessa.

Very quickly, like many young, secular Jews of his generation, Bronstein was drawn to the Communist revolutionary movement—partly out of Marxist idealism, partly out of disgust at the reactionary and anti-Semitic czarist government. He was only eighteen when he was arrested, with other members of his small, amateurish revolutionary cell, and exiled to Siberia. As with so many Russian radicals, however, Siberia was less a prison for Bronstein than a kind of finishing school. Bronstein married a fellow prisoner, Alexandra Sokolovskaya—also Jewish, like several other members of his cell—and had two children. He made contact with other Communists, and began to read the clandestine newspaper Iskra (“The Spark”), which he received hidden in the binding of an innocuous book.

Iskra was edited from London and Geneva by a group of Communists including Vladimir Lenin, and Bronstein decided he had to join them. With surprising ease, Trotsky—as he was now known on his forged or stolen passport—escaped from Siberia and crossed Europe, presenting himself in London as a new recruit to the cause. (It is ironic that, compared to the later brutality of the KGB and the Gulag, the czarist police system looks like benign neglect.)

It soon became clear that Trotsky was a brilliant writer: at their first meeting, Lenin greeted him with the words: “Ah, the Pen has arrived!” And it was by his pen that he became to known to revolutionaries inside and outside Russia, writing for Iskra and other illegal, but widely read, publications. In 1905, when the first Russian Revolution broke out, Trotsky smuggled himself back into St. Petersburg, where he discovered that he was equally magnetic as a platform orator. Still just 25, he became head of the Petersburg council, or Soviet; when the revolution was crushed, he was arrested again and escaped again.

By 1917, Trotsky’s peregrinations and expulsions had led him to New York, where he arrived “to a hero’s welcome among emigrant socialist sympathizers from the Russian Empire,” especially Jews—he wrote a series of articles for the Forverts, the socialist Yiddish daily. Indeed, one of the ironic themes of Service’s Trotsky is the way the revolutionary kept finding himself in Jewish milieux, despite his adamant refusal to claim a Jewish identity. As Service explains, in his chapter “Trotsky and the Jews,” he followed an orthodox Marxist line on matters of nationality and religion: “In his own eyes, he had ceased to be a Jew in any important sense because Marxism had burned out the fortuitous residues of his origins.” He detested Zionism and the Jewish socialist Bund. Yet it is striking how many of Trotsky’s closest comrades were non-Jewish Jews, just like himself. One might even say, though Service does not pursue the subject this far, that the aggressive rejection of Jewish particularity was the form in which Trotsky, and many Jews like him, lived their Jewishness.

When the czar was overthrown, in February 1917, Trotsky immediately began planning to get back to Russia, and he arrived at Petersburg’s Finland Station on May 4, a month after Lenin. Service traces the complex, ever-shifting circumstances of that revolutionary year, the advances and feints and retreats of the Bolsheviks, until they finally seized the capital, under Lenin and Trotsky’s leadership, in October. Then came the years of triumph and power and cruelty; and then came the great fall, which turned Trotsky the commissar into the socialist martyr described by Farrell.

Starting in 1923, as Lenin was crippled by strokes, Trotsky and Stalin waged a bureaucratic and propaganda war over who was entitled to succeed him. Trotsky entered the battle with many advantages. His highly visible role in the Civil War had made him iconic; he was still a brilliant and popular writer. Most important of all, he was Lenin’s own choice. The ailing leader dictated a “testament” in which he warned that the struggle between Stalin and Trotsky had the potential to split the Communist Party, and he came down firmly on Trotsky’s side: “Stalin is too crude and this inadequacy…becomes intolerable in the position of General Secretary.”

The real question, as Service convincingly frames it, is why Trotsky, given all these advantages, allowed Stalin to outmaneuver him so decisively—to the point that, by 1928, Trotsky had been stripped of office, expelled from the Party, and finally exiled from the USSR. Service concludes that Trotsky, perhaps unconsciously, did not really want to replace Lenin as sole leader of the country; that is why he “lacked the decisiveness for a concerted advance on power.” While Stalin expertly manipulated the Communist Party apparatus, packing the Politburo with his supporters, Trotsky remained aloof, arrogant, inflexible. When it came to making speeches to big crowds or writing scorching pamphlets, no one could beat Trotsky. When it came to making friends and allies, he could not be bothered.

And there was one other factor in Trotsky’s failure of will. In 1917, just after the revolution, Lenin had wanted to appoint him as Commissar for Internal Affairs, which would have made him head of the secret police. Trotsky refused, on the grounds that “it would be inappropriate for a Jew to take charge of the police in a society pervaded by anti-Semitism. If Jews were seen to be repressing Russians, a pogrom atmosphere might be provoked.” For the same reason, he initially resisted taking charge of the Red Army, and rejected the invitation to become Lenin’s second-in-command in 1922. “The party’s leadership was widely identified as a Jewish gang,” Service writes, and “Trotsky continued to believe that his own prominence in government, party and army did practical damage to the revolutionary cause.”

If Trotsky allowed Stalin to get the better of him at the crucial moment, it may have been because he still feared the consequences of a Jew heading the Soviet government. Of course, such scruples made no difference to the enemies of the Jews. By the time Hitler took to power, thanks in part to the Germans’ fear and hatred of “Judeo-Bolshevism,” Trotsky had long since been made a non-person in Stalin’s USSR. The rabbi who made the famous quip was right: “It’s the Trotskys who make the revolutions, and the Bronsteins who pay the price.”

Adam Kirsch is a contributing editor to Tablet Magazine and the author of Benjamin Disraeli, a biography in the Nextbook Press Jewish Encounters book series.

When Bush administration figures like Paul Wolfowitz and Richard Perle urged America to fight Islamic fundamentalism and build democracy in Iraq, and when Jewish liberals, in turn, denounced those figures as neoconservatives, they were reenacting some of the same battles the New York intellectuals fought seventy years ago, when the combatants were called anti-Communists and anti-anti-Communists. Indeed, as Kimmage notes, the label neoconservative—which in the last decade has become almost a kind of anti-Semitic code word—was coined in 1943 by Dwight Macdonald, a charter member of the New York intellectuals, to describe former leftists who had abandoned their radical aspirations.

There is no shortage of books about the New York intellectuals—the mostly Jewish circle of writers clustered around Partisan Review—and their ideological schisms. But Kimmage offers a new perspective on this familiar story by focusing on an unlikely pair of protagonists. Lionel Trilling and Whittaker Chambers could not have been more different in terms of personality and background. Trilling, the child of Eastern European Jewish immigrants, was a quintessential New Yorker, who spent his whole career at Columbia University; Chambers, a WASP from Long Island, came to see New York as a symbol of America’s decadence, preferring to live on a remote farm in Maryland. Trilling wrote magisterial literary essays for Partisan Review; Chambers wrote blunt polemical articles for Time Magazine. Most important, Trilling was a reserved, professorial figure, while Chambers was a man of action, a Communist spy turned anti-Communist prophet who figured in one of the most scandalous trials of the century.

Yet The Conservative Turn shows that, from the time they met as classmates at Columbia in the 1920s, Trilling and Chambers followed similar intellectual courses. In the early 1930s, with America sunk in the Depression and fascism on the march in Europe, they were among the many American leftists who turned to the Soviet Union for inspiration. The appeal of Communism was especially strong to American Jews, who saw in Russia’s great experiment” the promise of a world without poverty, injustice, or prejudice, including anti-Semitism. Hadn’t Lincoln Steffens, the crusading liberal journalist, visited the Soviet Union and proclaimed, I have the seen the future and it works”?

For Trilling, becoming a fellow traveler was primarily an intellectual commitment, not a practical one. He did nothing more to advance the revolution than joining a Communist front organization, the National Committee for the Defense of Political Prisoners, and writing some pro-Soviet book reviews. Chambers was much more deeply involved in the Communist cause. After joining the Party, he became a secret agent for the Kremlin, helping to organize a spy ring among mid-level New Deal bureaucrats in Washington D.C. He even tried to recruit Lionel and Diana Trilling, asking if they would help him by acting as a drop” for secret messages. They declined, not wanting to follow Chambers so far into the realm of espionage.

But in the mid-1930s, both Trilling and Chambers underwent a crisis of conscience about Communism. Like many radicals, they were troubled by the show trials in which Stalin eliminated many of his fellow Bolsheviks. It was becoming increasingly hard for anyone paying attention to deny that Stalin, like Hitler, was a totalitarian dictator. Yet in the late 1930s, the so-called Popular Front, which united liberals and Communists in a common crusade against fascism, had blinded many American leftists to the true nature of the Stalin regime. For Trilling and Chambers, it now became imperative to repent of their former error, and to convince those who still believed in the USSR to do the same. Even more than the Soviet Union itself, their target was the Popular Front mentality so common among literary and intellectual people—the belief that Communism was just an advanced form of liberalism, rather than liberalism’s greatest enemy.

Kimmage documents the month-by-month evolution of Trilling’s and Chambers’s political views, studying their correspondence in tandem with their published work. Trilling’s literary criticism seldom addressed contemporary politics directly, yet by quoting extensively from his (still unpublished) letters, Kimmage shows that political motivations were never far from his mind. Writing to the drama critic Eric Bentley in 1946, Trilling declared, I am willing to say that I think of my intellectual life as a struggle, not energetic enough, against all the blindness and malign obfuscations of the Stalinoid mind of our time.”

In his sensitive readings of Trilling’s criticism, Kimmage shows how this struggle” shaped his interpretation of writers like Matthew Arnold and E.M. Forster. What Trilling admired in them was a habit of mind that shunned false certainties and embraced difficult realities—what he named, in his influential 1949 book, the liberal imagination.” An art that was morally complex and free from self-righteousness,” Kimmage summarizes, would express the spirit of political anti-communism.”

It is no surprise, then, that when Trilling produced his only novel, The Middle of the Journey, in 1947, he would choose the dilemmas of communism and anti-communism as his subject. What is more surprising is that he chose to base one of the novel’s main characters directly on Whittaker Chambers. Chambers’s clandestine work for the Communists, followed by his dramatic apostasy from the Party, made him unpalatable to both the pro- and anti-Stalinist factions of the left. Kimmage describes a Halloween party Chambers attended in 1938 where New York intellectuals, including the Trillings, shunned him; Diana refused to shake his hand, since it was figuratively covered in blood.

In The Middle of the Journey, Lionel Trilling used Chambers’s dramatic story and enigmatic character as the basis for Gifford Maxim, one of the novel’s protagonists. The few people who read the book when it first appeared would have had no problem identifying Maxim’s original, since Chambers’s history was well known among the New York intellectuals. Just a year after Trilling’s novel appeared, however, Chambers was to become notorious across America and around the world, thanks to his starring role in the Alger Hiss affair.

Kimmage recounts the well known story of how Hiss—a member of Chambers’s old spy network, who had risen to become a leading member of the New Deal establishment—was denounced by Chambers as a Communist and a traitor. The ensuing trials, in which the disreputable, unattractive Chambers testified against the well-connected, personable Hiss, polarized the country. To the anti-Communists, Hiss was a perfect example of the way liberalism, fellow travelling, and active support of the USSR all bled into one another. To most liberals, by contrast, Hiss was the innocent victim of Chambers’s ideologically motivated denunciations. Even after Hiss was convicted, the left remained convinced of his innocence. Not until the end of the Cold War and the opening of the Soviet archives was it established beyond a doubt that Hiss was indeed a spy.

In the aftermath of the trial, Chambers became a hate-figure to the left and a hero to the right. The spectacle of the liberal elite rallying around Hiss helped to galvanize the nascent conservative movement; to this day, Kimmage shows, when a gutter polemicist like Ann Coulter writes that liberals are traitors, she is drawing on tropes from the Hiss case. Kimmage follows Chambers’s subsequent career and offers a close reading of his memoir, Witness, which became one of Ronald Reagan’s favorite books. Between Witness and The Middle of the Journey, Chambers and Trilling helped at once to create and to document the “conservative turn” in mid-century American politics. Kimmage’s book offers a thorough guide to this still powerfully resonant chapter in our history.