In the summer of 1965, six years of secret listening came to an end with a single order from the White House. The agents returned to the tailor shop, reached behind the baseboard, and pulled out the microphone they had hidden there. President Lyndon Johnson had decided that the Federal Bureau of Investigation’s practice of planting hidden microphones in the meeting places of organized crime, without warrants, without judges, on the word of J. Edgar Hoover alone, was a violation of civil rights.

He ordered them all removed. In Chicago, the most important device sat on the second floor of a bespoke tailor shop on North Michigan Avenue, where for six years the men of the Outfit had sat on the sofas, waiting for their measurements, and talking. The microphone had a name. The 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 that came before it. The film *The Outfit*, released in 2022, is set in that shop, or rather in a shop that resembles it. The writer and 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 an entire fictional story about a night of betrayal and murder around that seed.

Mark Rylance is the tailor, a criminal family uses his back room, and there is a tape everyone wants. 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 at all. It begins with a correction, because the date Moore gave was wrong.

And the reason it was wrong is the most interesting part. Because in 1956, the FBI was not wiretapping 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 like before 1957. Hoover had spent two decades insisting that there was no such thing as a national crime syndicate. Bank robbers, yes. Communists, certainly.

But an organized Italian-American organization with bosses, territories, and a ruling commission? Hoover said it was a myth invented by journalists. His agents in Chicago were not allowed to work on organized crime as a subject of investigation. The men who ran the city’s illegal activities, Tony Accardo, Paul Ricca, Murray Humphreys, had been doing so for a quarter century without the Bureau having a single file on them worth reading.

Then came November 14, 1957. Apalachin, New York. A state trooper noticed too many luxury cars parked at a rural estate and set up a roadblock. Sixty or more of America’s top gangsters fled into the woods in their silk suits.

The story was in 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 area and build cases against them.

The Chicago office got a special squad. That squad included a 31-year-old agent named William F. Roemer Jr. Roemer is the only 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.

He was born in Indiana in 1926. He boxed at Notre Dame so well that he was never beaten, under the name Zipp. He served in the Marines during the war. He joined the FBI in 1950, and according to his account in his memoir *Man Against the Mob*, published in 1989, he arrived at the Top Hoodlum squad in Chicago 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 they needed to say face to face. You could surveil Murray Humphreys for a year and not hear a single 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, with nothing they could use. So the question became: where do they go that we can penetrate?

Here is where it gets interesting. The answer, according to Roemer’s account, came through field surveillance. Agents following the Outfit’s top men noticed that a number of them kept showing up at the same address. A bespoke tailor shop on North Michigan Avenue in Chicago’s Magnificent Mile, on the second floor above the street.

Solano’s shop. The tailor, Jimmy Solano, was by all accounts a genuinely honest craftsman who made suits for men who could afford good suits. And 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 to be measured.

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 point of view. It is a legitimate business with a legitimate reason for wealthy men to visit again and again.

Nobody looks twice. It sits on a busy commercial street full of pedestrians, so it is easy to spot a tail and easy to lose one. It has a private back room, and it belongs to a man they trust, who has no motive to talk and every reason to stay silent. For the mob, it 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. For 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. The 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 only to enter the shop but to have a route out for the wire. Roemer wrote that the technical work was done by a specialist agent, and that the entry team included him and his colleagues on the squad.

Ralph Hill and Marshall Rutland are the two names that appear consistently in the accounts of the Chicago wiretaps. The entry, according to Roemer’s account, took place at night in the summer of 1959, after the agents had watched the building’s routine for weeks. They opened the lock, went upstairs, and fixed the microphone behind a baseboard in the back room, near where the men sat. Some accounts recall that it was placed so that the heating unit helped conceal it.

They ran the wire. They were out before morning. Roemer wrote that it took more than one night to make everything work, and that the fear in each entry was not of 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 live in July 1959. Some accounts give the date as the 29th. Roemer wrote that the first sound the device captured was the voice of Humphreys. Now, was it legal?

The answer is no, and it is important to say so plainly. There was no warrant. No judge authorized it. The only approval required was Hoover’s own, and he gave it on the grounds that the Bureau was gathering intelligence, not evidence for court.

That distinction is what allowed the whole 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 1920s and 1930s, 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 heads, and the police commanders. He was the man who decided which cases were 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 over Chicago in a way no informant could have, because an informant would have had to be present in the room.

It recorded the deliberations of the First Ward, the political machine in the downtown area through which the Outfit penetrated City Hall. It recorded how cases were handled in the courts. It recorded who was paid. Roemer wrote that within a few years, the Bureau’s understanding of the mob went from nothing to a complete organizational chart, with Accardo at the top as the retired elder, Giancana as the operational 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 repeated it again and again. A second microphone, which the agents called Mo, went into the Armory Lounge in Forest Park, the restaurant Sam Giancana had made his headquarters. Others followed.

By the early 1960s, the Chicago Top Hoodlum squad was effectively attending the mob’s meetings on a daily basis. A special group of agents did nothing but listen, transcribe, and archive. What they heard from Giancana went beyond Chicago. The bug in the Armory Lounge captured his relationship with Frank Sinatra and his ties to the Kennedy family around the 1960 election.

The details of what those tapes contained have been disputed among historians for sixty years, and we will only say what is certain: they existed, and the Bureau took them seriously enough to brief Attorney General Robert Kennedy on them. That is 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 complication, and it comes from three directions at once. The first was the mob itself. They were not stupid. By the early 1960s, Roemer wrote, Giancana in particular had become convinced he was under surveillance, and he began holding his meetings in cars, on street corners, and in places that changed daily.

The bugs still caught the older men, Humphreys most of all, 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 complication 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 mysterious 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 go after 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 for wanting to know what the Bureau’s microphones were picking up, especially where politicians were concerned. And in the spring and summer of 1965, as the scope of the illegal wiretap 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 had been planted. The 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 FBI in Chicago was deaf. Six years of daily transcription stopped in a single week. What happened next surprised everyone on the team. Because they had assumed the intelligence would simply stop.

What they had not counted on 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. And 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 turned them. The most famous, Richard Cain, was a corrupt Chicago police officer who joined the mob and then, according to Roemer’s account, secretly joined again. Cain was shot dead in a sandwich shop in 1973. His murder was never solved.

The mob’s leadership paid for those six years too, if not in court. Sam Giancana was jailed for contempt in 1965 for refusing to testify before a grand jury, and when he got out, he left the country. He was shot dead in the basement of his home in Oak Park in June 1975, while cooking sausages, on the eve of his testimony before a Senate committee on the CIA. That murder 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 for contempt. Roemer, who had listened to the man for six years, wrote about that death with something close to regret. Tony Accardo, the retired old man 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 mob. He died in June 1996 at the age of 69, two days before his 70th birthday. Now, *The Outfit* was released in March 2022 by Fox Features. Mark Rylance plays Leonard Burling, the tailor.

Dylan O’Brien and Johnny Flynn play the sons and soldiers of the Boyle family, a fictional mob that uses the back room of his shop. Zoey Deutch plays his assistant. It is a small-scale drama. One night, one shop, one tailor.

Graham Moore, the Oscar winner for writing *The Imitation Game*, has said in interviews that it all started with the wiretap in the tailor shop, which he described as the first one the FBI planted in 1956. The film’s mafia family is fictional. The audio tape is invented. The betrayals, the bodies in the back room, and the tailor’s hidden past are all fiction, and it does not claim otherwise.

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 is the direct child of the Apalachin meeting 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 have been 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 continuous, daily visibility inside the mob’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 happened to run Chicago, and for six years the government listened to them through his wall, and according to the public records, no one ever told him. That silence, in its own way, is more unsettling than anything in the film.

Here is what the true story reveals. Everything that broke the Chicago Outfit over the next forty years, the informants, the organizational charts, the Family Secrets trial of 2007, traces its origin to those six years of transcripts. When the Family Secrets prosecutors presented the structure of the mob to a jury in 2007, the shape of the chart they used was the same one Little Al had first drawn in 1960. Those transcripts exist because a handful of agents broke a lock one night without a warrant, on the authority of one man, in a program the President of the United States shut down as unconstitutional once he realized its scope.

The mob was brought down by something that was itself against the law. Not a comforting thought, but it is simply a recorded fact. A tailor made suits, the gangsters sat, the government listened, and nobody in that room was supposed to know.

For six years, nobody did.