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At some point in 1928, Mickey showed up at the doorstep of brother Harry the pharmacist, who had moved to Cleveland. When Mickey told him of his plans to turn professional, Harry took one look at his five-foot, three-inch, ninety-six-pound sibling and laughed. Once he saw Mickey in the ring, however, the laughing stopped. His little brother was good. Harry began to nurse a new plan: Mickey would go pro, and he (Harry) would manage his career. A confrere told Harry that if he was serious, Mickey needed professional instruction—the best professional instruction. He needed to go to New York. And so, at the age of sixteen, Mickey Cohen was signed over to two boxing managers and sent to New York City to start training at the most famous boxing gym in the world. He was supposed to learn how to fight. Instead, he would discover a new world—the world of organized crime.

      LOU STILLMAN’S GYM—Mickey’s destination—was a dump. “The atmosphere,” George Plimpton would later write, “was of a fetid jungle.” The windows were never opened. The floors went years between cleanings. Members of the public, who could watch the action for a quarter, were encouraged to smoke; Stillman, a moody and acidulous former private eye, thought it toughened fighters up. Perhaps it did, for by 1929 the dungeonlike space on West 57th Street was the most revered gym in the world, a favorite training spot for boxers such as Jack Dempsey and, later, Joe Louis. Mickey was one of the roughly 150 fighters who rented lockers and trained there, a group whose quality ranged, in Stillman’s words, from “jerk squirts to top-of-the-heaps.” In his interactions with the men he was training, Stillman didn’t bother to distinguish between the two.

“Big or small, champ or bum, I treat ’em all the same—bad,” he once said, in what Budd Schulberg described as his “garbage disposal voice.” “If you treat them like humans, they’ll eat you alive.”

The men surrounding Mickey were indeed a tough lot. The gym had been founded by philanthropists whose goal was not to rescue the city’s toughest youth from a life of violence—there seemed to be little hope of that—but rather to encourage them to use their fists instead of knives or guns. The donors were reportedly happy with the gym’s results: Stillman later calculated that only a dozen of his fighters went to the electric chair. He wasn’t counting those who made their way into the rackets.

“A card of membership in Stillman’s is an Open Sesame to low society in any part of the world,” wrote New Yorker correspondent Alva Johnston in 1933. “The place is one of the centralizing institutions of the underworld; rival low-life factions meet here casually under a flag of truce, as the rival financial and social mobs fraternize at the opera.”

This was sixteen-year-old Mickey Cohen’s new world.

He gave it a go.

Every day Cohen did his roadwork in Central Park and then reported faithfully to Stillman’s (whose motto was “Open Sundays, Mondays, & always”). He appeared on the cards on several occasions at the old Madison Square Garden. He got to know Tony Canzoneri, the featherweight champion of the world. He struck up an acquaintance with Damon Runyon, bard of the New York underworld. As a fighter, Mickey gained a reputation for scrappiness and versatility, if not talent. A natural flyweight, Mickey also routinely fought bantam and featherweight bouts. In 1933, he went up against featherweight champion Alberto “Baby” Arizmendi (like Mickey, a sometime-resident of Boyle Heights) in Tijuana, losing by a knockout in the third round. All in all, Cohen was a good, journeyman fighter. As he said later, “I wasn’t the worse. Neither was I the tops.”

Still, his heart wasn’t in it. Boxing increasingly disgusted him. Every year in the ring brought another disfigurement—a broken nose, inch-long scars under both eyes, a two-inch scar on the left wrist. But it wasn’t the pain of these injuries that upset Mickey most; rather, it was the physicality of the sport—the sweat, the blood, the blows, the tie-ups, the embraces. Mickey became compulsive about his personal hygiene. After every fight, he’d spend hours in the bathtub or shower.

Moreover, he wasn’t making any money. Life as a boxer-in-training had its upsides. His managers paid his expenses, bought his clothes, and gave him pocket money. But the fact of the matter was, Mickey now never had more than $15 or $20 in his pocket. Who did? The watchful Irish and Italian men in the bleachers who periodically came in to check on their fighters’ progress—men like Owney “The Killer” Madden, fresh out of Sing Sing, and Joe “the Boss” Masseria, the king of New York’s Italian underworld (until his assassination in 1931). To Mickey, they were simply “the people.” Even then, he knew that these were the men he wanted to associate with. He just didn’t know how. So he decided to return to Cleveland and try his hand as a full-time gangster. He was not welcomed into the fold.

Unlike New York City, where the smartest Jewish and Italian gangsters had learned to cooperate, Cleveland was still primarily Italian territory. Mickey tried to fit in by becoming a kind of honorary Italian himself, making Italian friends, picking up bits and pieces of various Italian dialects, and perfecting such forms of assault as “the Sicilian backhander.” Cleveland’s top Italian gangsters, brothers Frank and Tony Milano, just laughed at the “Jewboy,” as they called him, who so wanted to be Sicilian. That changed when establishments across Cleveland started seeing Mickey behind the barrel of a gun. Mickey had decided that if the Cleveland outfit wouldn’t take him in, he would hang out his own shingle as a “rooter,” a holdup man.

Mickey’s first target was a “half-ass gambling joint… way out the west end of Cleveland in the produce area.” An informer had tipped them off to a high-stakes grocers’ craps game. That night, Mickey and a few associates stormed the joint and grabbed $5,000. They struck again the following week, then two or three times a week. Mickey soon had a troupe of seven and was routinely hitting gambling joints, cafes, and whorehouses across Cleveland. It seemed a highly satisfactory life. Days were spent sleeping and playing cards. Nights were exciting and frequently rewarding, both financially and psychologically. Armed robbery, Mickey found, did wonders for his self-esteem.

“It made me equal to everybody,” Mickey later recalled. “Even as small as I was, when I whipped out that big .38 it made me as big as a guy six foot ten.”

Great Depression or no Great Depression, business was good. At the end of a successful heist, Mickey’s little crew worked around his inability to add or subtract by stacking all the bills up separately—Lincolns here, Hamiltons there, Jacksons here (Grants were rare; Franklins, alas, were virtually unknown)—and then dividing each pile among the participants (“one for you, one for me …”).

The Cleveland mob was remarkably calm about Mickey’s behavior—until he hit a bookie parlor under its protection. Fortunately for Mickey, one member of his crew had an uncle in Buffalo who was in “the highest echelons of ‘the people.’” This uncle made some phone calls to “the people” in Cleveland, and Cleveland reacted magnanimously. Instead of punishing the upstart heister, the Cleveland mob made Mickey an offer. Mickey could operate as before (as long as he stayed clear of mob-protected operations). In addition, the Cleveland outfit (as it was sometimes called) would offer him a $125-a-week retainer. In exchange, Mickey would perform certain tasks for the local mob and, on occasion, for friends elsewhere.

Cohen was delighted. He accepted at once. And, almost as quickly, he fucked up.