The buildings at 600 N. Michigan Ave., left, and 620 N. Michigan Ave., center right, on Sept. 4, 1967, in downtown Chicago. Celano's Custom Tailors shop was located at 620 N. Michigan Avenue. (Sigmund J. Osty / Chicago History Museum)

Celano’s Custom Tailors on the Magnificent Mile was the prototype of the setting for the movie “The Outfit”: a fitting room where Chicago gangsters plotted their dirty work unaware they were being recorded by a hidden microphone.

For years, the FBI eavesdropped on the real-life Outfit via an army-surplus microphone planted in Celano’s second-floor offices at 620 N. Michigan Ave. Juicy tidbits of the recordings are preserved in the memoirs of William Roemer, an FBI agent known for “black bag” surveillance gambits that tiptoed around the law’s fine points.

On Nov. 1, 1960, a mobster was heard calling out numbers to another one pulling the lever of Celano’s adding machine: “one more thousand, 10,000, 4,000, 6,375 ….,1,560, 6,060 …, 4,400, 1,200. Add it. What’s our third?”

It was the monthly accounting of bookies who paid a “street tax” to the Outfit as the price of doing business and staying alive.

Once, the agents regretted stashing their microphone behind a radiator, a detail mimicked by the screenwriters of “The Outfit.”

Joey Glimco, head of the mobbed-up taxi driver’s union, was talking with Murray Humphreys, who ran the mob’s labor racketeering division. The subject was Roger Touhy, a recently assassinated mobster.

A hearse carries the casket and remains of Roger Touhy, 61, at Mount Carmel Cemetery in Chicago on Dec. 18, 1959. (Chicago Tribune historical photo)

“What was it with Touhy?” Glimco asked.

“Well, I’ll tell you, Joe,” Humphreys replied.

For the next several minutes, all that could be heard was the whooshing sound of the radiator’s valve letting off steam. Then Humphreys voice was audible again: “… and that is the way it was, Joe.”

The bugging was triggered by a 1959 memo Roemer sent to FBI Director J. Edgar Hoover. It reported his discovery that the clandestine headquarters of mob boss Gus Alex was in James V. Celano’s tailoring shop.

“The informant stated that this private office contains a bar, television, radio, desk, and couch,” Roemer wrote. Alex met there daily with “his underlings who he utilizes as the leaders of Chicago Crime Syndicate activities in the First Ward of Chicago.”

Gus Alex hides his face while sitting in a car at the detective bureau on Sept. 9, 1946, before his release on a habeas corpus writ. Police had hoped to question him about a shooting. (Chicago Tribune historical photo )

Hoover had taken heavy flack after local cops — not the FBI — led a raid on a 1957 gathering of mobsters in rural Apalachin, New York. He responded with a hastily created “Top Hoodlum Project” and made a critical assumption: Given the number of corrupt elected officials, mobsters would be tipped off should the FBI ask a judge for permission to wiretap them. A microphone had to be planted secretly, Hoover decreed. Roemer was enlisted for the job.

“If we got caught, we were not to identify ourselves as FBI agents, and we were to attempt to escape without being identified,” Roemer recalled in his memoir, “Roemer: Man Against the Mob.” If they were apprehended and it came out they were with the FBI, “then the Bureau would denounce us,” Roemer wrote.

He almost faced that contingency. A wire had to be run from the microphone to a distant recorder that agents could monitor. The optimal time to do that was on Sunday, when both the tailor shop and the restaurant below it were closed.

But as they were carrying out the operation, an agent fell through the crawl space between the shop and the restaurant. “We had to stop what we were doing, go back to the office for some plaster and paint, then break into the restaurant in order to patch up the ceiling,” Roemer recalled.

Former FBI agent and author William Roemer in 1989. Juicy tidbits of FBI recordings at a Chicago tailor shop are preserved in Roemer's memoirs. (Bruce McClelland/for the Chicago Tribune )

It took eight Sundays, but the recording system was successfully installed. With it, Roemer realized his childhood fantasy of busting Chicago gangsters — the pineapple-sized microphone was code-named “Little Al,” after Al Capone. The boxing titles Roemer had won at the University of Notre Dame and as a Marine gave him the swagger to stand toe-to-toe with Capone’s successors, when the opportunity occurred.

What motivated Celano to front for the Outfit is murkier. Perhaps the tailor’s youthful fantasy was palling around with mobsters. He was a chronic gambler, and addicts are notorious for being in hock to bad guys.

When Celano blew $20,000 in Las Vegas, he was put on notice by Alex, who ran the Outfit’s gambling operations. The mobster’s ominous words were captured by the FBI’s recorder.

“It is a sucker’s game. You can’t win out there, you understand. We got the percentages rigged all in our favor,” Alex explained. “I don’t allow nobody around me who gambles. A couple thousand, okay, but no gambling.”

Little Al’s success inspired the FBI to plant another microphone in Sam Giancana’s headquarters, the Armory Lounge in suburban Forest Park. The door to its backroom had a peephole, marking its origin as a speak-easy, a Prohibition-era underground saloon.

Sam "Momo" Giancana leaves the courtroom in the Federal Building after appearing before Judge Campbell before being locked up in jail on June 1, 1965. (William Yates/Chicago Tribune)

A flashy mobster, Giancana dated Phyliss McGuire, a famous Las Vegas entertainer. At one time, as he picked her up at O’Hare International Airport while being tailed by Roemer, Giancana and Roemer got into a shouting match. “Roemer, you lit a fire tonight that will never go out!” Giancana vowed.

Roemer wanted to retaliate. But he couldn’t ever use the wiretap evidence because the microphone had been placed illegally and any conversations it collected would be inadmissible in court.

Roemer was as well known to the hoodlums as they were to him, and he wasn’t above asking an occasional favor. When the FBI flipped Bernie Glickman, a fight manager with alleged underworld ties, agents got word the Outfit had put a hit order on him. As there wasn’t yet a witness protection program, Roemer begged Outfit boss Tony Accardo to spare the boxing-world eminence.

The mob’s elder statesman did, but only after taking a parting shot. “Roemer, I thought we were supposed to be the bad guys,” Accardo said, according to Roemer’s book. “It seems to me that here you are the f*** bad guys.”

In a 1969 trial, Roemer testified that the Chicago office of the FBI had 12 bugs in place. The chatter was always interesting, like the time Roemer said he listened to Richard Cain, a mobbed-up cop, brag about taking newspaper columnist Jack Mabley “for a tour of the ‘kinky’ nightclubs in Chicago.” While the tour brought unwanted attention to those mob joints, Outfit honchos “decided that Cain’s making himself a confidant of the very influential Mabley was a plus in the long run,” Roemer wrote.

Former FBI agent and author William Roemer in Arizona in 1989. (Bruce McClelland/for the Chicago Tribune)

After days of dealing with Chicago’s underworld, Roemer would hop aboard a commuter train for South Holland, where he lived the suburban good life. He coached a Little League team, and his wife was a Cub Scouts den mother. They would come into Chicago for an occasional night out.

Sometimes his two worlds collided. A favorite restaurant of Roemer’s, Jim Saine’s, abutted the Tradewinds, the Outfit’s Rush Street hangout. Fearing its phones were tapped, mobsters started making calls from Saine’s wall phone. The sight appalled the respectable clientele of Jim Saine, who brought his problem to Roemer.

He found Marshall Caifano, the mob’s top enforcer, sitting at Saine’s bar with a girlfriend in lowlife attire.

“Marshall, this is our place,” Roemer said. “Your place is next door. Let’s make a deal. You stay on your side of the wall, we’ll stay on our side, okay?”

In 1972, Roemer was transferred to a pre-retirement post in Phoenix, where he would keep tabs on Joe Bonnano, the aged and ill leader of a New York crime family. Fellow agents threw a going-away party for him in Chicago. So too did the Outfit, in a way.

Upon his arrival in Phoenix, Roemer was invited to the wedding of the daughter of an old friend. The father of the bride was a former Chicago police officer who was also a gambler with Outfit acquaintances. Among the other guests were Chicagoans with monikers like “Large” and “The Wizard of Odds.” Some he’d arrested. All were delighted to learn he’d be there and eager to exchange reminiscences.

It seems that mobsters were as fond of telling old war stories as Roemer, the G-man who saved the Top Hoodlum Project from being stillborn by cleaning up the mess the FBI made in a restaurant underneath Celano’s Custom Tailors.

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