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No one in Chicago sought out Gardner for the Capone squad, either. Instead, the agent had asked earlier in the year to be transferred back to the city and the special agency unit, now run by Jamie. He listed “twofold reason . . . one is to better my status, and the other is to be nearer to my family.” (He had relatives in Michigan.) His supervisor in New York approved the transfer request without expressing regret. Jamie, who would soon move over to the Secret Six, was loath to turn down the transfer, under the theory that, in the aftermath of the Golding disaster, beggars couldn’t be choosers.

Gardner wouldn’t be the only misfit on the Capone squad. Johnson and Froelich realized the squad needed a “pencil detective”—that is, an agent with the kind of methodical, detail-oriented mind to take bits and pieces of seemingly disparate evidence and string them together to create a clear picture of organized intent. Forty-year-old Lyle Chapman, a Colgate University graduate and a Prohibition agent in Indianapolis, had that kind of mind; the problem was getting him to use it. “I remember my knees shook like jelly when I got the orders telling me what was up,” he would later say of his assignment to the Capone squad. “
Frankly, I pondered how to get out of it.” This was the kind of reaction his superiors had grown to expect from him.
Six months before Johnson requested Chapman for the team, agent B. F. Hargrove Jr. wrote to his supervisor that Chapman “just simply does not want to work or do things that we request him to do and on such occasion he puts up some excuse as to why he doesn’t want to. . . . It has got to a point where none of the agents wants to work with him.” Chapman had received hardly any satisfactory efficiency reports during his four years in the bureau, and none in the previous two years. That summer, the head of the Indianapolis division, Dwight Avis, reprimanded him in writing, closing:
“I suggest that it would be very advisable for you to show a little more initiative in your work.” It was the last entry in Chapman’s file before his transfer to the Capone squad.

A friend of Chapman’s, thirty-four-year-old Bernard Cloonan, also joined the operation. He was a former marine and a member of the prominent veterans organization the Forty and Eight.
Eliot would describe him as “a barrel-chested giant who fitted the popular conception of the typical Irishman with his black hair, ruddy complexion and ready smile.” Cloonan and Eliot had joined the Chicago office at the same time, and Eliot had been awed by his sheer physical presence. Cloonan, he figured, would provide the muscle as needed.

Rounding out what would become the core group were the “drawling” Virginia native Mike King, hard-boiled former private investigator Jim Seeley, and bashful former Pennsylvania state trooper Tom Friel, who was so shy he could barely speak in mixed company. The Capone squad was an eclectic group, there was no doubt about that. Eliot, the youngest member of the team and the boss, would struggle to figure out the best way to motivate them. But that difficulty had little to do with his youth and inexperience. In 1930, nowhere in America did one size fit all. Three decades later,
pharmacist and World War I–era baseball player Davy Jones would point out just how diverse the country had been: “You know, we didn’t have the mass communication and mass transportation that exist nowadays. We didn’t have as much schooling, either. As a result, people were more unique then, more unusual, more different from each other. Now people are all more or less alike, company men, security-minded, conformity—that sort of stuff.” Sure enough, there wasn’t a company man to be found on the Capone squad—except perhaps for its young leader.

Eliot brought his team together for the first time in late December 1930. They all seemed to recognize just how big their new job was. The world outside the Transportation Building had turned especially cruel in the past year.
Gang violence had spiked again, with Capone declaring that when it came to gang war, “the law of self-defense, the way God looks at it, is a little broader than the law books have it.” When a football fan set off fireworks at Union Station while changing trains on his way east for the St. Mary’s–Fordham game, a panic ensued.
Homicide detectives and a morgue truck screamed to the station, expecting to find wounded thugs and civilians scattered about. Worse than the rise in gang violence was the reason behind it: the 1920s’ economic boom had proved to be little more than
drunken wishful thinking. The stock market had crashed late in 1929, throwing the country into depression. The federal government’s response—most notably the Smoot-Hawley Tariff Act—only intensified the downward spiral. By now, a year after Wall Street’s collapse, the depression had become the Depression. The unemployment rate approached a third of the available nonfarm work force and was still rising. On his way into the office every morning, Eliot picked his way around homeless men sleeping on the sidewalk and stutter-stepped around queues at soup kitchens.
A friend remembered him frequently handing over loans of $5 and $10. He wasn’t earning much as a special agent but he knew he was lucky to be earning anything at all. Now and again the unemployed would be marching down State Street when Eliot emerged from the Transportation Building. These parades included banging drums and chanting calls for government action. For months, the men worked themselves into a frenzied state over and over. But after a year of unrelieved misery, hope was slipping away. Eliot, hitting the street for lunch one day, found himself watching a straggly mockery of a march. The men passing by, operating on muscle memory, shuffled down the street like survivors after the end of the world. They made no noise at all. They had no demands left.


The Depression was
so
real that it became unreal,” recalled Julia Walther, a Chicagoan whose family company tottered but managed to survive. “There was a horror about it, with people jumping out of windows. I remember the first time motoring under the Michigan Avenue Bridge, under those streets, where the
Tribune
is, and seeing not hundreds, but thousands of men, rolled up in their overcoats, just on the pavement. I remember being so horrified, so overwhelmed.” It was, she said, the searing “first experience of something, of realizing that life was not the way you had thought it. Until you actually saw someone dying, you can’t know what war is like. Now I have an inkling of what the Depression was for some people, although I never slept under the bridge.”

By the end of 1930, there was no escape from this unreality. Optimism about a recovery being right around the corner had curdled into bewildered acceptance that this terrible, ugly new world had settled in for good. Sally Rand, the performer who caught Jack McGurn’s eye at the Paramount Club, was a ballerina in her early twenties when the economy collapsed. She hadn’t made it big, but she’d made it, traveling across the country with a company run by the Russian choreographer Adolph Bolm, Anna Pavlova’s onetime partner. The economic implosion put an end to that. “
Suddenly,
all the copybook maxims were turned backward,” she would remember nearly four decades later. “How could it be that a man who had been at his job thirty years couldn’t have a job? How could it be that a business that had been in business for a lifetime suddenly isn’t any more? Friends of mine who had been to Harvard, Yale and Princeton jumped out of windows. With accuracy. The idea of the stock market quittin’ was unbelievable.”

Rand, the beloved daughter of a conservative West Point man, turned to nude fan dancing to survive. It was that or prostitution. “It was economically sound,” she would later joke about her act, “because I didn’t have any money to buy anything” to wear on stage. Even with this titillating routine, she managed to land work only because she knew someone who knew a couple of low-level gangsters. The hoods paid a visit to the owner of Chez Paree, one of Chicago’s most popular nightclubs. “It’d be a terrible thing if this place got a stink in it,” they said. The owner blanched: “Wha-wha-wha-
what
?” Rand went on that night, fans fluttering, to cheers and whistles.

Capone took advantage of the dire situation. He opened up a soup kitchen downtown, the largest in the city. A straightforward, elegant sign over the door declared, “Free Soup, Coffee, and Doughnuts for the Unemployed.” Mary Borden, working on a magazine article about her wild native city, was not fooled. “
The bread line outside of Al Capone’s soup kitchen,” she wrote, “stretched down one of these bleak, windswept streets past Police Headquarters. I had been [inside the police offices], turning the leaves of what they call the Death Book, most dreadful of all souvenir albums in the world. And there was undoubtedly a connection between the two lots of men, those who stood shivering outside the soup kitchen and those who, enclosed in the covers of the police album, lay sprawled on the bare boards of matchbox rooms or crouched in the corners of taxis with their heads bashed in. For Al Capone is an ambidextrous giant, who kills with one hand and feeds with the other.”

Borden was making a connection that those in Big Al’s soup line didn’t want to think about anymore. To them, the St. Valentine’s Day Massacre seemed like a very long time ago. Men who still had jobs and homes could worry about Mob violence and how gangsters preyed on the weak and troubled. The down and out could worry only about themselves. “Good-Hearted Al,” they mumbled when asked about the underworld boss. If Capone wanted to call himself a twentieth-century Robin Hood, that was fine with them, as long as his kitchen stayed open. On top of this new image of good-hearted Al, the economic immolation had brought back the
see-no-evil, hear-no-evil crowd in local political circles. Borden feared the situation had produced “a creeping civic paralysis, the spread of some moral intoxication or fever that, like the effects of certain drugs, will produce in time a complete immunity from the sensation of horror or disgust or fear.”

This much was certain: Johnson, Jamie’s Secret Six, and the incipient Capone squad were truly on their own. After being booted out of office in the mid-1920s by a reformer, Big Bill Thompson had returned to city hall. The gangs were running Chicago’s city government once again, including the police department. A socialite, trekking to a soirée on the roof of one of the city’s best hotels late in 1930, would recall the odd feeling she had as “we walked through the seething, smoke-laden lobby of the hotel; I suppose that the crowd of men who eyed us over their large cigars, their hats pushed back onto the backs of their heads as we stepped past in satin slippers and ermine coats, represented as tough a crowd of crook politicians and crook business men as any you could find in the world.”
As she headed upstairs, along with her fellow “pretty, delicate girls, such nice, boyish men,” to a party that would be awash in illegal liquor, she grew angry at the state of official Chicago:

Suppose that crowd downstairs hadn’t chosen to let us have our party? Suppose they decided not to let these attractive people have any parties any more? Suppose they told them to clear out of the town altogether? Weren’t they helpless? Wouldn’t they quickly disappear? What could they do about it? Fight? Well, why didn’t they fight, then? Why wait? What actually were they doing in regard to the governing of this town of theirs? Nothing.

The socialite perfectly captured the conflicted angst of the city. Chicagoans high and low hated Prohibition, but their very own flouting of the dry law had helped make their lives—their entire world—scary, without order or reason. Increasingly, people wanted to be saved from themselves. The crook politicians and crook businessmen would continue to do nothing; no one expected otherwise. But that didn’t mean no one was willing to step forward and fight. The perfect moment had arrived, at long last, for the hated Prohibition Bureau to produce a hero.

CHAPTER 7

The First Step

T
he Capone operation was a hydra: bootlegging, extortion, union racketeering, prostitution, gambling. A dogged investigator had myriad entry points to exploit, as well as many blind alleys he could stumble down. But not the Capone squad. Their focus, Eliot told his men, was the breweries—and only the breweries. They were going to find them and knock them out, one by one.
The brewery business made for a prime target, Eliot said, “having the most capital invested . . . the most complete organization, the quickest turnover and the greatest income.” And it was especially vulnerable, he pointed out, because “their product was bulky and because they have the toughest transport problem.”

This very specific objective sounded easy enough to achieve, but despite all the money poured into police payoffs, the Outfit actually went to considerable trouble to hide its brewing work. The Mob used decoy buildings, trompe l’oeil techniques to conceal entire rooms, lookouts, and advance and trailing cars to secure deliveries. The syndicate frequently moved its heavy equipment among dozens of buildings across the city, and its beer trucks regularly changed their routes. Counterintuitively, little family stills, many of them under Capone’s control, were relatively easy to find; they were less professionally run, less secure, less mobile—and, more than ever, neighbors talked. The big breweries, the ones that pulled in the serious money and should have been difficult to hide, were much tougher to track down.

In its first weeks, the new special team focused on cultivating informants, surreptitiously following bootleggers, and figuring out where best to place phone wiretaps, a relatively new law-enforcement practice. Eliot’s life was changing fast—again. In the year and a half between the end of the Chicago Heights operation and the creation of the Capone squad, he had settled into a routine at the bureau, mostly tracking down small-time brewers in the suburban and rural areas outside Chicago.
He’d even had time for a real personal life. Being so much younger than his siblings, he’d
essentially been an only child growing up. He’d always been uneasy about sharing his physical and emotional space. But that finally had begun to change. He was in love. When they were alone together, he and Edna became comfortable opening up about their feelings. They began to trust not just each other but themselves. After several months of exclusive dating,
they had married on August 9, 1929, in suburban Oak Glen and moved into a small apartment near Palmer Park on Chicago’s South Side. The rent was $65 a month. For the first time in his life Eliot was out from under his parents’ roof. And he found that he loved married life; he loved being the man of the house. He and his new bride spent almost all of their free time at home together, reading or listening to music or working on jigsaw puzzles. It was the happiest he had ever been. But now, a year after their marriage vows and with an astonishing career opportunity before him, the honeymoon was over. No longer was he on the periphery of the action at the bureau. He was right back in the middle of it. Eliot once again moved into an all-encompassing work mode. He went out to the shooting range every day, until he became the best shot in the office. He diligently made a list of every known gangster in the region, along with each man’s known haunts and associates. His address book filled up with killers. He worked late into the night and then got up early in the morning after just a couple hours of sleep. He discovered that the best way to find Capone’s breweries was to keep it simple: he and his men hung around outside speakeasies, all hours of the day and night. “
We knew that regularity was necessary in their operation, and it wasn’t long before we learned of the special hauls on Fridays in preparation for Saturday speakeasy business,” Eliot would later tell a reporter. For a while, the squad tried following the trucks after their delivery, but that led nowhere useful. A truck would deliver beer, and the next day it would deliver office furniture. Then it might sit on the street for days. It turned out to be a better bet to stay with the booze.

The squad noticed that, as a tavern filled up on a busy weekend night and the place started rocking, bartenders would regularly heft empty beer barrels into the alley. “
The first observation we made was that the barrels had to be used over and over again, and that if we could successfully follow a beer barrel from a speakeasy, we would wind up locating a Capone brewery,” Eliot noted. In February, Eliot assigned Leeson and Seeley to park outside one of the city’s biggest speakeasies. The empty beer barrels stacked up in the alley as the night wore on. Hours went by, the bar emptied out, and the lights went off. Finally, shortly before dawn, a truck rolled up to the
alley and a couple of men nonchalantly loaded the barrels into the back and drove on. Leeson and Seeley followed the barrel truck without detection—no small feat with the streets empty in the middle of the night—to a building near Comiskey Park, the Southside home of the White Sox baseball team. They had their first breakthrough. In the following days, the team rented rooms near the building and began watching it around the clock. They quickly discovered they hadn’t found a brewery; it was a barrel-cleaning facility.

Now Leeson’s expertise as a “tail man” really came into play. About twenty-five trucks filled with empty barrels rumbled into the building each day. A similar number left the facility, presumably bound for breweries. Eliot was determined to be careful. He knew they’d get only one shot at this; any hint that the dry cops were onto them and the Outfit would close up shop and disappear. So as trucks left the building with freshly cleaned barrels, Leeson and Seeley—or sometimes two other agents from the team—would follow them, but only for a few blocks before turning off. Each truck was at the center of a small convoy, with sedans cruising ahead and behind it, looking out for anything suspicious. Each morning, the agents picked up the chase where they had left off the previous day, swinging out behind the convoy and following for a handful of blocks before turning down a side street and letting the truck rumble on.
Sometimes they would follow by driving ahead of the convoy and watching through the rear-view mirror, or they’d tail the beer truck by driving along parallel streets. Finally, Leeson and Seeley managed to track a truck to a garage on the West Side. “
The garage was on Cicero Avenue near Western Electric Co.,” Eliot remembered. “Across from the garage was a field with tall weeds.” That’s where the two agents crouched in the middle of the afternoon. They were still there at three in the morning, when at last the garage came to life. The truck, they realized, was only there to be “cooled off.” Now two Ford coupes emerged from the building and set off down the street, one after the other. The men in the coupes slowly canvassed the neighborhood, peering into parked cars and down alleys “to detect any observers.” Yet Leeson and Seeley managed to stay hidden. Once the all-clear was given, the truck exited the garage—with the agents hustling to get to their car undetected. The truck drove down South Cicero Avenue and pulled into a long, one-story brick building with a sloped roof. Leeson and Seeley drove on past. The Capone squad had found its first brewery.

***

The team’s progress pleased Eliot, and for good reason. In a few short weeks, they had found Capone’s barrel-cleaning plant and one of his major breweries, and they also were beginning to see results from the first batch of wiretaps they’d put in. They had bugged a hotel—possibly the Lexington, where Capone often stayed—as well as casinos and whorehouses in Cicero run by the Outfit.

These developments were highly encouraging, but personnel issues sucked some of the excitement out of Eliot’s job. For much of January 1931, at the end of sixteen-hour days in the field, Eliot found himself sitting blurrily at his desk writing memos to Washington that didn’t exactly put the fledgling Capone squad in the best light. The biggest problem was Gardner, the former football hero whom Eliot had been so excited to have join the team. Just days after reporting for his new assignment in December, Gardner had requested thirty days’ leave for personal reasons. Eliot passed the request along to Froelich, who turned it down. They needed more men, not fewer, Froelich told him, so allowing a leave of absence at this time was “out of the question.” But Gardner never took no for an answer. He began making his request anew to every supervisor in the vicinity, receiving a staccato burst of brush-offs in response, most referring him back to Froelich and Johnson.
On January 18, a Sunday, Gardner called Seager at home and petulantly declared that if his leave wasn’t approved immediately he’d resign. Seager raised no objection. That night, Gardner checked out of his hotel and disappeared.

From the very first day of the Capone squad’s existence, Eliot, in what would become a pattern throughout his career, embraced his men as brothers. He didn’t allow himself to see anything but their best qualities, homing in on the good bits until those qualities alone defined their characters. The agents would have various complaints and requests over their months together, and Eliot sent off determined memos to Washington attempting to satisfy them. He sought promotions and pay raises for his men, even though the bureau’s budget was being severely cut. He gave them glowing efficiency reports and recommendations. The one consistent exception was Gardner. It had taken less than a month for the football hero’s act to wear thin. Eliot’s memos about Gardner’s conduct were brisk and factual, no more. He made no special effort on his behalf. When Gardner rematerialized a couple of weeks after walking away from the job, Eliot accepted him back on the team without comment. With the discovery of the brewery on South Cicero Avenue, he needed all the men he could get,
and the bigger and stronger the agents the better. But he wasn’t happy about it.

Unlike most of his men, Eliot had no military background, other than ROTC in school. He was not a man’s man, as much as he wanted to be. Even at twenty-eight, he remained repressed and unnaturally shy, a stranger to himself as well as others. He’d spent his childhood playing with his older sisters and a small group of boys from the block. His Friday evenings had been taken up schlepping pans at his father’s bakery instead of knocking heads on his high school’s football team. His life had been insular, self-contained.
One high school friend remembered him being “uneasy in social settings.” During lunch break in the school cafeteria, Eliot preferred reading Sherlock Holmes stories to chatting with whoever might be sitting across from him. “Once you started talking to him,” the friend said, “he loosened right up and was fine. He just didn’t ever take the first step.”

Now, as leader of his own special unit in the Prohibition forces, he had to take the first step. He had to be a leader. Eliot could be found sitting in his office at seven every morning, chewing on his fingernails. The anticipation of the team’s first paramilitary action made him nauseous. Eliot was eager—probably overly so—to show results, to prove himself worthy of his new position. He might be bashful, but he wanted to win; he would do almost anything to win. His men picked up on their young boss’s drive. They had been dubious of him because of his youth and self-consciousness, but now, whether he realized it or not, they were growing to respect him. They understood he was one of them, and that no one was going to outwork him.
On January 20, just six weeks after being assigned to Johnson’s special squad, Eliot sent a report to Dwight Avis, now the new chief of the Special Agency Division at the bureau’s Washington, DC, headquarters. “At the present time several forces are brought into play in Chicago and the operations of the Capone syndicate have for the last few days been absolutely stopped,” he wrote. “After experiencing great difficulty, we have been able to secure telephone taps covering the various headquarters’ spots of the Capone gang and are in a favorable strategical [
sic
] position to obtain considerable information relative to their workings as soon as operations again begin.”

The long, detailed memo impressed Avis, who would become one of Eliot’s bureaucratic champions. He responded that he could “readily appreciate the difficulty that you are having in keeping men on the job in connection with this special work.” He was referring to the fact that Leeson
and Chapman had been called out of town to give testimony in trials. Willebrandt was gone, but the Justice Department had finally become serious about prosecuting Prohibition violations. Avis told Eliot he would reassign Special Agent W. Bruce Murray from Kansas City to Chicago to assist the squad for a couple of weeks and promised to push for the assignment of a Philadelphia-based agent named Paul Robsky, whom Eliot had requested. He also added that he was not surprised to hear about Gardner’s “misconduct, as he has resigned three or four times from the service, I understand, under similar circumstances.”

It’s impossible to know what Eliot meant about the Capone syndicate being “absolutely stopped.” The squad was just beginning to get stakeouts and other operations under way. Perhaps the squad’s early, probing raids—Eliot admitted they hit a few “dry holes” in their first attempts—had made the gang briefly go into turtle mode. More likely the young agent was just trying to puff himself up.

Whatever he meant, Eliot was clear about one thing: he was just getting started.

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