The chief agent looked at the man across the desk and saw everything wrong with him. Isidore Einstein was around forty, five foot five and two hundred and twenty-five pounds, balding, with a soft round face, several chins, and thick round spectacles. He had spent years behind a window at the post office. He looked, in every respect, like a man who could not chase down a bootlegger, and the chief told him so — he wasn’t the type.
Izzy had an answer ready. That, he said, was exactly the point. A tall, hard-jawed man with a federal look about him would never get past a speakeasy door. Nobody would sell whiskey to someone who looked like the law. What a Prohibition agent needed was a face no one would ever suspect, and a manner that put people at ease, and the ability to talk to New Yorkers in whatever language they happened to speak. Izzy had all three. He was hired — among the very first men to sign on with the Southern New York district of the new Prohibition Unit. Agent Number 1, he would call himself, and eventually put it on the cover of his memoir.
The Job Nobody Wanted to Do Well
The Eighteenth Amendment took effect in January 1920, and it was, almost from the first day, a law without an army. The federal government had banned the manufacture and sale of alcohol across a nation that had no intention of stopping. Speakeasies opened by the thousands in New York alone. The agents assigned to shut them down were underpaid, easily bribed, and — most usefully to the bars — easy to spot. A doorman learned the look fast.
Izzy Einstein did not have the look. That was the entire strategy, and he understood it better than the bureau that hired him.
His first attempt taught him what not to do. He walked into a Brooklyn establishment that prided itself on smelling out agents, announced cheerfully that he was a Prohibition officer just appointed, and asked to buy a drink. The doorman laughed him in — the joke being that no real agent would ever say such a thing. Izzy ordered his whiskey, got it, and then, in his excitement, drank it. When he produced his badge, the bartender grabbed the bottle and bolted, and Izzy was left holding an empty glass and no evidence at all.
He did not make that mistake twice.
The Funnel in the Vest
The problem was physical: to arrest a man for selling liquor, an agent had to prove liquor had been sold, which meant keeping the drink. So Izzy engineered a solution and wore it. Into the breast of his vest he fitted a small funnel, connected by a rubber tube to a flask hidden in a pocket. When a bartender poured him a drink, Izzy would raise the glass, tip his head, and — mid-motion — divert the pour down the funnel and into the flask. He appeared to drink. He appeared, over a long night, to get pleasantly drunk. He was in fact assembling a corked, labeled evidence sample for every bar he entered, marked with the establishment’s name and the time of sale.
Then he brought in his partner.
Moe Smith was an old friend, a cigar-store owner and sometime boxing manager, and he was built along the same lines as Izzy — broad, round, cheerful, entirely unthreatening. Together they looked less like federal officers than like two men who had wandered in looking for a good time, which was precisely the effect. Moe would station himself near the door while Izzy worked the bar. The two of them, between 1920 and 1925, would become the most effective and by far the most famous Prohibition agents in the country.
A Hundred Disguises
The method was theater, and Izzy had a gift for it. He spoke Yiddish, German, Polish, and Hungarian fluently, with enough Russian, Italian, Spanish, and French to pass, and he could carry an accent to match whatever neighborhood he was standing in. He played the violin. He read a room the way an actor reads a house.
The disguises followed the map of the city. In a district of German speakers he was a German; on the Lower East Side he slipped into Yiddish; among Italians he was Italian. But he went further than accents. He drove a coal wagon up through the Upper East Side and, working from the driver’s seat, arrested sixteen bartenders in a single hour. He sold fruit from a Bronx cart and ice in Brooklyn. He pulled on a white coat to get inside a speakeasy that catered to physicians near Mount Sinai. He walked into a restaurant full of musicians carrying a trombone, played a chorus of “How Dry I Am,” and arrested the men who had just served him.
His favorite trick required no costume at all. On a bitter winter night he stood outside a bar in his shirtsleeves, shivering, looking like a man in genuine distress, until Moe came along, threw an arm around him, and steered him inside to warm up with a drink. The bartender, moved by the sight of a freezing man, obliged. Both men were under arrest before the glass was empty.
Over five years the pair claimed to use more than a hundred disguises. Their faces were no secret. Speakeasies kept albums of enforcement agents’ photographs behind the bar, Izzy’s among them, and it barely mattered: the man in the picture was never the man who walked in — not the coal driver, not the fruit peddler, not the musician with the trombone under his arm. Once, in a bar with his own photograph on hand, Izzy took bets that he was the agent in the picture, collected from everyone who paid up, and arrested them.
Thirty-Five Seconds in New Orleans
Izzy’s reputation grew until reporters treated him as a kind of civic performance, and he obliged them with a running bet: drop him in any American city, and he would find an illegal drink within thirty minutes. He kept score. Chicago took twenty-one minutes. Atlanta, seventeen. Pittsburgh, eleven.
New Orleans set the record that nobody would beat. Izzy arrived by train in 1923, climbed into a taxi, and asked the driver — as any thirsty traveler might — where a man could get a drink in this town. The driver reached under his seat and produced a bottle for sale. From station to arrest: thirty-five seconds.
The number was funny, and Izzy meant it to be. But it was also the plainest possible measurement of how thoroughly the law had failed. A federal agent could not travel the length of a cab ride in a major American city without being offered a felony.
Too Famous to Keep
By the mid-1920s Izzy and Moe had made 4,932 arrests, won convictions in roughly ninety-five percent of the cases, and seized something like five million bottles of liquor. In New York they accounted for nearly two-thirds of all Prohibition arrests. They were also, by then, on the front pages constantly — quoted, photographed, adored by a public that found them far more entertaining than the law they enforced.
That was the problem. Their superiors did not enjoy watching two rotund showmen become more famous than the bureau itself. In November 1925 both men were dismissed, officially for failing to measure up to the unit’s standards of efficiency — a charge that was, given the numbers, plainly absurd. The record for arrests in the country belonged to the two men just fired for not making enough of them.
They landed on their feet. Both went into the insurance business and did well; by 1930 Izzy was a special representative for New York Life, selling policies into the teeth of the Depression — sometimes, he liked to boast, to the very bootleggers he had once put in front of a judge. He wrote a memoir, Prohibition Agent No. 1, that told the whole story of the disguises and the arrests and the funnel in the vest, and mentioned Moe Smith almost not at all — his partner, Izzy explained, had no wish to go down in history as Prohibition Agent No. 2.
Prohibition itself lasted until 1933, when the country gave up the experiment entirely. Izzy Einstein had spent five years proving, thirty-five seconds at a time, how easily the law could be broken.