Ernst Sedgwick Hanfstaengl remains perhaps the most incongruous of the psychopaths, evil banalities, and fanatical maladaptives who surrounded Nazi dictator Adolf Hitler. With his wealthy background, prominent American ties (his relations included the New England Sedgwicks, and his maternal grandfather was one of the pallbearers at Abraham Lincoln’s funeral), and Harvard education, Hanfstaengl made an unlikely National Socialist. Throw in his ready wit and lively sense of humor, and the man who briefly served as the Nazi Party’s foreign press secretary fit into Hitler’s circle about as well as a penguin among birds of carrion. How, you have to wonder, did an inveterate practical joker known as Putzi (a nickname from childhood) end up consorting with the most demonic figure of the 20th century?

Peter Conradi addresses this and other questions in his new biography, Hitler’s Piano Player: The Rise and Fall of Ernst Hanfstaengl, Confidant of Hitler, Ally of FDR, with mixed success. The book is worth reading if only because Hanfstaengl, while never more than of third-rank importance in the Nazi hierarchy, is a perfect representative of an enigmatic type: the intelligent and warm-blooded soul who somehow comes to serve a monstrous regime. And this type is of no small importance. Hitler’s success in wooing a petty bourgeois scared witless by communism and left discombobulated by years of economic hardship was one thing; his capturing the allegiance of people like the happy-go-lucky Hanfstaengl, who liked nothing more than to sing Harvard fight songs and who held an annual party to celebrate George Washington’s birthday, quite another.

There was certainly nothing in Hanfstaengl’s background to suggest he’d one day find himself in the gallows fraternity that constituted Hitler’s circle of intimates. Born in 1887, he had a happy childhood in Munich, graduated from Harvard (where he spent more time carousing and banging on the piano than studying) in 1909, and found America so attractive a proposition that he returned to its shores in 1911 to open a branch of the family’s lithographic business. He even remained in the country when it declared war on Germany in 1917.

Had Hanfstaengl never left the States, he would be remembered, if at all, as a kind of amiable eccentric, or as one of the writer Djuna Barnes’ more unlikely—given his decidedly Lurch-like appearance and her preference for women—lovers. But in 1921, he and his wife, Helene Elise Adelheid Niemeyer Hanfstaengl—like him of mixed German and American heritage—decided to return to Germany, which was still reeling from its defeat in war and groaning under the weight of the reparations exacted by the Treaty of Versailles.

Like many Germans, Hanfstaengl didn’t find the Weimar Republic to his liking. He also shared the conservative loathing of the Marxist revolutionary movements that had seized power in Russia and threatened Germany following World War I. Finally, he was, despite his genial disposition and liberal background, prey to that most insidious of bugbears: hatred of the Jews. Given these antipathies, he was—like all too many of his fellow countrymen—more ready than he might have conceded to abandon his democratic principles in exchange for order, security, and a renewed sense of German dignity.

Asked by an American friend to provide his opinion of a Bavarian political upstart named Adolf Hitler, Hanfstaengl went to his first National Socialist meeting in November 1922 harboring the reservations natural to an aristocrat confronted with the hoi polloi. But he was instantly entranced by the former Austrian corporal with the goofy mustache who seemed transformed the moment he began to speak.

Unlike Hitler’s less educated supporters, Hanfstaengl didn’t swallow Hitler’s message hook, line, and sinker. Conradi notes that to Hanfstaengl, “some of Hitler’s ideas seemed downright absurd.” He was particularly put off by Hitler’s dismissal of the importance of the United States and particularly wild-eyed brand of anti-Semitism. Nevertheless, he viewed Hitler as a diamond in the rough. Like such German conservatives as Gen. Kurt von Schleicher—who helped bring Hitler to power through his behind-the-scenes machinations only to end up murdered by the Nazis during the infamous Night of the Long Knives—and Franz von Papen—who helped talk the aging President Hindenburg into the fateful decision to approve a coalition government that made Hitler chancellor and von Papen his deputy—Hanfstaengl foolishly thought he could “tame” Hitler, curing him of his more demagogic tendencies and molding him into the kind of statesman who could have Germans singing “Deutschland Uber Alles” again.

Toward this end, Hanfstaengl set out to gain the former Austrian corporal’s ear. He succeeded to such an extent that by 1923 Hitler was stopping by his home on an almost daily basis, although his appeal to Hitler had less to do with his sage advice than his willingness to play Hitler’s beloved Wagner on the piano for hours on end. The aspiring politician also appreciated the fact that Hanfstaengl, with his many social connections, could help open the doors of the rich and influential—doors long closed to the rough-necked Hitler, whose idea of formal attire consisted of a cheap blue suit and a dog whip, and whose genuine amazement upon discovering hot-water taps in the Munich hotel room of a rich benefactor amused Hanfstaengl no end.

Unlike many of the “intellectual chauffeurs” (as Hanfstaengl referred to them) with whom Hitler chose to associate, Hanfstaengl seems to have maintained a degree of independence around the Führer, even as his own power and influence waned, due in equal parts to the gradual usurpation of his foreign-press duties by Joseph Goebbels’ Propaganda Ministry and his own political missteps. He saw, more clearly than most, Hitler’s glaring flaws, refused to engage in the new custom of using the “Heil Hitler” greeting, and was always willing to disagree with Hitler—a tendency that provoked the latter to “loud bursts of fury.”

Nevertheless, he remained a Hitler booster—and made various dubious contributions to German Kultur including a “Hitler Song Book,” a film version of the life of Nazi “martyr” Horst Wessel, and, most bizarrely, a compilation of anti-Hitler cartoons accompanied by his own written attempts at refuting them—well into the ’30s. In this way, he whiled away the years that saw the mass arrests in the wake of the Reichstag Fire, the opening of the first concentration camps, the systematic curtailment of civil liberties, the Night of the Long Knives, Kristallnacht, and many other Nazi excesses. But Hanfstaengl’s indiscreet nay-saying—which seems to have gotten back to Hitler through such conduits as the English fascist Unity Mitford—and a concerted Putzi-bashing campaign by Goebbels worked to turn Hitler against Hanfstaengl. This, in turn, led to the bizarre “practical joke”—in which Putzi was put on board a plane to civil-war-ravaged Spain and informed in-flight that he would be parachuting behind enemy lines on what amounted to a suicide mission—that culminated in his fleeing Nazi Germany in February 1937. Taken into custody by the British an enemy alien, Hanfstaengl found himself a prisoner in Britain,

Canada, and finally the United States, where he became part of a secret “black propaganda” project approved by President Franklin Roosevelt himself.

Was Hanfstaengl a misguided idealist with a blind eye for the diabolic or a garden-variety scoundrel determined to ride anyone’s coattails to power and wealth? Or was he, as he himself claimed, an increasingly troubled fellow traveler whose only goal was to civilize Hitler and curb his worst abuses? It is here that Conradi, who writes a lively prose and tells a good story, founders. In addition to his failure to provide footnotes, and his general murkiness on the subject of dates, he can’t seem to decide for himself how to regard Hanfstaengl.

At first, Conradi seems to parrot the Hanfstaengl party line—to take at face value assertions by Hanfstaengl that as his love affair with the Nazi party waned, he stuck around only to allay the damage. And there is some evidence to support this view. Conradi cites examples in which Hanfstaengl helped to extricate people from jams with the Nazis and openly—and unwisely—denounced members of Hitler’s party as “criminals.” Indeed, it’s hard to know whether Hanfstaengl was demonstrating bravery or stark insensibility by deriding Goebbels as a “vicious, satanically gifted dwarf” and the “pilot-fish of the Hitler shark.”

But just when you begin to read Hitler’s Piano Player as a kind of innocent verdict on Hanfstaengl, Conradi drops damning bombs from contemporaries such as the American Will Moore, who described him as a “ruthless example of a ruthless government,” and U.S. Consul George Messersmith, who said of Hanfstaengl: “He is constantly trying to give the impression to Americans, to correspondents, and to foreigners that he is a conservative and really out of sympathy with many acts of the party, but in fact this is merely a pose.”

In the end, it is left to Egon Hanfstaengl, Putzi’s son, to provide the most plausible analysis of the wellsprings of his father’s character. Egon describes him as a Cassandra, a man whose own arrogance invariably precluded the possibility of his being heeded. The elder Hanfstaengl’s dreams of helping Germany, first by serving as a kind of consigliere to a loose-cannon dictator, and later by helping the Allies to defeat that dictator, were forever being undone by his patrician conviction that everyone would be better off if everyone just shut up and listened to him. Hanfstaengl emerges as the proverbial back-bencher, destined to grow dissatisfied with the powers that be in whatever place he found himself, whether it be the Weimar Republic, Nazi Germany, or the United States.

When all is said and done, you’re left with the portrait of a deeply flawed human being with, at the very least, a bad case of moral myopia. Yet there is something undeniably likable about Hanfstaengl; unlike Hitler’s other henchmen, he had at least a few redemptive qualities, such as a lingering sense of decency, perhaps best demonstrated by the fact that, upon being placed by the British in their mixed Nazi-Jewish intern camps, he gradually found himself drifting toward the Jewish side, if only out of a revulsion at the beatings he saw meted out to them by their Nazi fellow prisoners. As Conradi documents, Hanfstaengl once helped save the lives of Jewish prisoners who were being attacked.

Indeed, to Hanfstaengl’s credit, he seems to have viewed even his own destiny with a certain equanimity. In the end, his life, as he himself acknowledged, played out less as a tragedy than as an “enigmatic, grim, Gilbert and Sullivan farce.” CP