The order came from the White House, and it ended six years of listening. Agents returned to the tailor shop, reached behind the baseboard, and pulled out the microphone where it had been hidden. It was the summer of 1965. President Lyndon Johnson had decided that the FBI’s practice of planting hidden microphones in organized crime meeting places, with no warrants, no judges, and no approval beyond the word of J.
Edgar Hoover, was a violation of civil rights. He ordered every one of them removed. In Chicago, the most important device sat on the second floor of a custom tailor shop on North Michigan Avenue, where mob men had sat on couches for six years, waiting for measurements and talking. The microphone had a name.
Agents called it Little Al, after Al Capone. And what it heard, according to the testimony of the men who listened, damaged the Chicago Outfit more than any informant, indictment, or newspaper in the thirty years before it. In 2022, the film *The Outfit* was set in that shop, or rather in a shop like it. Writer-director Graham Moore said the whole idea came from a piece of history he stumbled across: that the FBI planted one of its earliest listening devices in a Chicago tailor shop in 1956 to spy on the mob.
He built a complete fictional story of one night of betrayal and murder around that seed. Mark Rylance plays the tailor, a crime family uses his back room, and a tape that everyone wants appears. That is the fiction. This is the story of the real microphone: who put it there, how they got in, what they heard, and why it was never supposed to exist.
It begins with a correction, because the date Moore gave was wrong. And the reason it was wrong is the most interesting part of the whole story. Because in 1956, the FBI was not bugging the Chicago Outfit. In 1956, officially, the FBI did not believe the Chicago Outfit existed at all.
You have to understand what J. Edgar Hoover’s bureau was before 1957. Hoover had spent two decades insisting there was no such thing as a national crime syndicate. Bank robbers, yes.
Communists, certainly. But a structured Italian-American organization with bosses, territories, and a ruling commission? Hoover called it a myth invented by journalists. His agents in Chicago were not allowed to work organized crime as an investigative subject.
The men who ran the city’s illegal activities, Tony Accardo, Paul Ricca, Murray Humphreys, had been doing so for a quarter century without a single FBI file worth reading. Then came November 14, 1957. Apalachin, New York. A state trooper noticed too many expensive cars parked at a rural estate and set up a roadblock.
Sixty or more of America’s top mob bosses fled into the woods in their silk suits. The story hit every newspaper in the country by the next morning. Hoover, who had built his entire public image on knowing everything, had known nothing. Within days, he created the Top Hoodlum Program.
Every major field office was ordered to identify the ten most important organized crime figures in its territory and build cases against them. The Chicago office got a special squad. That squad included a thirty-one-year-old agent named William F. Roemer Jr.
Roemer is the one figure in this story who deserves a full introduction, because he is the reason the microphone existed and the reason we know what it captured. Born in Indiana in 1926, he boxed at Notre Dame well enough to never lose under the nickname “Zippy. ” He served in the Marine Corps during the war. He joined the FBI in 1950, and according to his own account in his 1989 memoir *Man Against the Mob*, he arrived on the Chicago Top Hoodlum squad knowing almost nothing about the Outfit, because the Bureau had made sure nobody knew anything.
What he and his colleagues found once they started looking was a real problem. The Outfit was disciplined in a way the New York families were not. Its leaders were never arrested. They did not talk on the phones.
They met in person, in places they controlled, and said what needed to be said face to face. You could surveil Murray Humphreys for a year and never hear one word he said. Roemer’s squad did exactly that for nearly a year and came back with license plate numbers and the names of restaurants, nothing they could use. So the question became: where do they go that we can get into?
The answer, according to Roemer’s account, came from field surveillance. Agents following the Outfit’s top men noticed that several of them kept turning up at the same address. A custom tailor shop on North Michigan Avenue in Chicago’s Magnificent Mile, on the second floor above the street. Solano’s tailor shop.
The tailor, Jimmy Solano, was by all accounts a genuinely honest craftsman who made suits for men who could afford good suits. The men who could afford them in Chicago in 1959 were Murray Humphreys, Gus Alex, Frank Ferraro, and sometimes Sam Giancana himself. But they were not there just for measurements. Surveillance showed them arriving and staying for hours at a time, sitting in the back room on the shop’s furniture, holding what were in effect board meetings.
Why a tailor shop? Think about it from their perspective. It was a legitimate business with a legitimate reason for rich men to visit again and again. Nobody gave it a second look.
It sat on a busy commercial street full of pedestrians, easy to spot a tail and easy to lose one. It had a private back room, and it belonged to a man they trusted, who had no motive to talk and every reason to stay silent. To the Outfit, the place was perfect. According to Roemer’s account, Humphreys chose it for exactly those reasons and had been using it for years before the Bureau noticed.
To the FBI, it was the first fixed location they had identified where the bosses spoke freely. Now they had to get in. This is the part about the mechanics of surveillance, and it is documented in Roemer’s own account, so we can be precise. The device itself was primitive by later standards.
Reports describe the microphones of that era as huge, the size of a softball, and they had to be wired. That meant a cable running from the microphone to a listening post, which meant the agents needed not just to enter the shop but to have a route to get the cable out. Roemer wrote that the technical work was done by a specialist agent, and that the entry team included him and his squadmates. Ralph Hill and Marshall Rutland are the two names that appear consistently in accounts of the Chicago buggings.
The entry, according to Roemer, happened at night in the summer of 1959, after the agents had watched the building’s routine for weeks. They picked the lock, went upstairs, and installed the microphone behind a baseboard in the back room, near where the men sat. Some accounts recall it was positioned so the heating unit helped hide it. They ran the wire.
They were out before morning. Roemer wrote that it took more than one night to get everything working, and that the fear on every entry was not the police. The fear was that one of the men who used that room would come back for something he had forgotten. Little Al went operational in July 1959.
Some accounts put the date at the twenty-ninth. Roemer wrote that the first sound the device captured was Humphreys’s voice. Now, was it legal? The answer is no, and it is important to say clearly.
There was no warrant. No judge authorized it. The only approval required was Hoover’s own, and he gave it on the basis that the Bureau was gathering intelligence, not courtroom evidence. That distinction is what allowed the entire program to exist.
Nothing Little Al heard could ever be shown to a jury. But everything it heard could be used to figure out who to chase, who to pressure, and where to look. And what it heard was everything. Here is the truth about Murray Humphreys.
He was Welsh, not Italian. He had been Al Capone’s political fixer in the twenties and thirties, and by 1959 he was, by the testimony of the agents who listened to him for six years, the smartest man in the Chicago Outfit. He did not run the rackets. He ran the judges, the aldermen, the union officials, and the police commanders.
He was the man who decided which cases got fixed and which cops got promoted. And he did most of that work, according to Roemer’s account, sitting on a couch at Solano’s. Over the following years, the bug documented the mechanisms of the Outfit’s control of Chicago in a way no informant could, because an informant would have had to be in the room. It recorded the discussions of the First Ward, the downtown political machine through which the Outfit reached into City Hall.
It recorded how cases were handled in the courts. It recorded who received the money. Roemer wrote that within a few years, the Bureau’s understanding of the Outfit went from nothing to a complete organizational chart, with Accardo at the top as the retired elder, Giancana as the operating boss, and Humphreys as the link to everything legitimate. But that is not the crazy part.
The crazy part is that Little Al worked so well that the Bureau did it again and again. A second microphone, which agents called Mo, was placed in the Armory Lounge in Forest Park, the restaurant Sam Giancana used as his headquarters. More followed. By the early sixties, the Chicago anti-racketeering squad was effectively attending Outfit meetings on a daily basis.
A special group of agents did nothing but listen, transcribe, and file. What they heard from Giancana went beyond Chicago. The bug in the Armory Lounge captured his relationship with Frank Sinatra and his connections to the Kennedy family around the 1960 election. The details of what those tapes contained have been disputed by historians for sixty years, but what is certain is that they existed and that the Bureau took them seriously enough to brief Attorney General Robert Kennedy on them.
That was the peak. Six years of America’s most secretive criminal organization talking, unaware, into an FBI microphone hidden in the wall of a tailor shop. Nothing like it happened before or after, because after 1965 it became illegal to try. Now the complications came from three directions at once.
The first was the Outfit itself. They were not stupid. By the early sixties, Roemer wrote, Giancana in particular became convinced he was being watched, and began holding his meetings in cars, on street corners, and in places that changed daily. The bugs still caught the older men, most of all Humphreys, who by all accounts was either less cautious or simply did not believe the Bureau had done it.
But the flow of information from the top began to narrow. The second was the law. The intelligence produced by the bugs could not be used in court. And the more the Bureau used it to build cases, the more defense attorneys asked where the FBI’s uncanny knowledge came from.
The answer, if it ever came out, would have destroyed every case it touched. The third was politics. Robert Kennedy, as attorney general, pushed the FBI to fight organized crime harder than anyone before him. But after his brother’s assassination in November 1963, his relationship with Hoover collapsed.
Lyndon Johnson, who inherited both Hoover and Kennedy, had his own reasons to want to know what the Bureau’s microphones were capturing, especially where politicians were concerned. In the spring and summer of 1965, as the scope of the illegal bugging program began to reach the White House and Congress, Johnson made his decision. Every microphone had to come out, not just in Chicago but everywhere. Roemer wrote that the order reached the Chicago office in July 1965, almost six years to the day from when Little Al was planted.
Agents went back to Solano’s. They took the microphone out from behind the baseboard. They went into the Armory Lounge and took out Mo. By the end of that month, according to the accounts, the Chicago FBI was deaf.
Six years of daily transcription stopped in a single week. What happened next shocked everyone on the squad. Because they had assumed the intelligence would simply stop. What they had not accounted for was how much they had already learned.
Six years of listening had produced something that no longer needed a microphone: a map. The Bureau now knew who answered to whom, who was fighting whom, who was being cheated, and who was afraid. From that map, Roemer and his colleagues built the thing that would replace the bugs: an informant program. They went after the men Little Al had identified as weak, or angry, or ambitious, and they turned them.
The most famous was Richard Cain, a disgraced Chicago police officer who joined the Outfit and then, according to Roemer’s account, secretly joined the Bureau. Cain was shot dead in a sandwich shop in 1973. His murder was never solved. The Outfit’s leadership paid for those six years too, though not in court.
Sam Giancana was imprisoned for contempt in 1965 for refusing to testify before a grand jury, and when he got out, he left the country. He was shot to death in the basement of his Oak Park home in June 1975, while cooking sausages on the eve of testifying before a Senate committee on the CIA. That crime also remains unsolved. Murray Humphreys died of a heart attack in November 1965, the same year the bug was discovered, hours after the FBI arrested him on contempt charges.
Roemer, who had listened to the man for six years, wrote about that death with something like regret. Tony Accardo, the retired elder that Little Al had placed at the top of the chart, outlived them all. He died in 1992 in his mid-eighties, without ever spending a night in prison. Roemer himself stayed in Chicago until 1980, then retired, moved to Arizona, and wrote five books about the Outfit.
He died in June 1996 at sixty-nine, two days before his seventieth birthday. So what does the real record say about the film’s premise? First, the date is wrong. It was 1959, not 1956, and it could not have been 1956 because Hoover would not have allowed the operation then.
The bug was the direct child of the Apalachin conference and the Top Hoodlum Program. Move it back three years and you erase the reason it existed. The claim that it was the first is disputed. Roemer believed it was the first FBI microphone planted against organized crime, and he may be right about Chicago.
The Bureau had used microphones in other contexts before. What is beyond dispute is that it was the first that made a difference, the first that gave the government a continuous daily view inside the mafia’s leadership. And the tailor. In the film, the tailor is the heart of the story.
In the records, Jimmy Solano’s name barely appears. There is no evidence he knew about the microphone. There is no evidence he was ever charged with anything at all. He sewed suits for men who ran Chicago by accident, and for six years the government listened to them through his wall, and according to the public record, no one ever told him.
That silence, in its own way, is more unsettling than anything in the film. Here is what the real story reveals. Everything that broke the Chicago Outfit over the next forty years, the informants, the organizational charts, the 2007 Family Secrets trial, traces back to those six years of transcripts. When the Family Secrets prosecutors showed the Outfit’s structure to a jury in 2007, the shape of the chart they used was the same one Little Al had drawn for the first time in 1960.
Those transcripts exist because a handful of agents picked a lock at night, with no warrant, on the authority of one man, in a program the President of the United States shut down as unconstitutional the moment he understood its scope. The Outfit was brought down by something that was itself against the law. It is not a comfortable thought. It is just the recorded fact.
A tailor made suits, mob men sat down, the government listened, and no one in that room was supposed to know. For six years, no one did.
