James (Cowboy) Mirro: The Chicago Outfit's Untamed "Wildcard"

James (Cowboy) Mirro wasn’t the most well-known name in Chicago Outfit history , but he ran with some of the deadliest men in the game. A tough-as-nails loanshark and gambler, Mirro operated out of Grand and Damen on Chicago’s Near West Side, where he built a reputation for both his criminal enterprises and high-speed police chases that made headlines more than once.

From his early days as a street thug alongside Sam Giancana to becoming a top lieutenant under Mad Sam DeStefano, Mirro was deeply entrenched in the Outfit’s world -- full speed ahead, rules be damned.

James Vincent (Cowboy) Mirro was born in Chicago on December 29, 1913, to Joseph and Mary Ann (nee Beichern) Mirro. His father was an Italian immigrant, while his mother immigrated from Luxembourg. Mirro also had several siblings, including Joseph, Anthony, Patsy, and Charlie.

The Family first lived at 1435 Elbern Ave. in Chicago before relocating to 1425 W. Fillmore St., though this appears to have been simply a street renaming rather than a location change.

On his WWII draft card, Mirro claimed he was self-employed, and his employer was “Grand and Damen.” It's kind of funny if you think about it.

James (Cowboy) Mirro

Mirro married a woman named Theresa (nee Serences). They had no children.

In 1950, he and his family lived at 1608 49th Ave. in Cicero. At the time, he claimed his occupation was a truck driver. The family later relocated to 1548 S. 61st St. in Cicero.

Other listed addresses included 1342 Austin Blvd., 1500 S. Austin Blvd., and 1608 49th St., all in Cicero.

1500 S. Austin Blvd., Cicero

Mirro stood 5 feet 8 inches tall and weighed 210 pounds. He had gray hair and brown eyes and wore glasses.

He owned Western Disposal Inc., a garbage firm, at 931 South State in Lockport, The Rainbow Lounge in Cicero, and the North Avenue Steakhouse at 8500 North Ave. in Melrose Park. The steakhouse was another notorious hangout for Mirro’s buddies, including Americo DePietto, Sam (Teets) Battaglia, Joseph (Gags) Gagliano, and Joseph (Joey Caesar) DiVarco.

His primary area of operation was Grand and Damen Avenues on Chicago’s Near West Side. Police described him as a West Side loanshark and gambler. He was known to hang out at the Lido Motel’s Guest House Restaurant at 2409 Mannheim Rd. in Franklin Park.

Lido Motel

Just the Beginning

Mirro reportedly got his start as a “street thug” alongside Sam Giancana before officially joining the Outfit’s ranks. He became a soldier sometime in the 1950s. Authorities said he was Anthony (Tough Tony) Capezio's nephew and a top lieutenant in Sam DeStefano’s crew.

In October 1964, newspapers reported that DeStefano and Mirro attended the murder trial of Michael Gargano, an ex-con, and Thomas Durso, a suspended Chicago cop. They were accused of killing Anthony (Lover) Moschiano in January of that year.

Moschiano had disappeared shortly before he was scheduled to testify in the narcotics trial of Gargano and Durso. He had been handcuffed and stabbed. His corpse turned up in the Des Plaines River that April.

Anthony (Lover) Moschiano

The day Mirro and DeStefano showed up in court was when a dope peddler turned informant named Leonard (Torpe) Fiorenzo testified, describing the killing.

Fiorenzo had accompanied Maschiano to Durso’s home in Westchester on January 21, 1964. After talking briefly, Durso asked everyone to go into the garage and ordered both Fiorenzo and Maschiano into his car. He then told Maschano to get out of the car and handcuffed him while Gargano stuffed his mouth with rags. Durso then forced Maschano to lie down in the trunk and stabbed him to death.

Thomas Durso

Michael Gargano

Moschiano had been murdered because he apparently “lost” $2,000 worth of heroin. After the murder, Durso told Fiorenzo that he was going to give him the “break of his life” and “let him go.” Durso said, “I think you can stand up and make some money selling the stuff.”

Then he said, “Look at me. I want you to see what happens to people who are short.”

Fiorenzo went to the police the next day.

Leonard (Torpe) Fiorenzo

Both Durso and Gargano were convicted and sentenced to 100 to 150 years in prison.

FBI #4617657

In July 1935, Mirro was held for questioning in the robbery of the Liggett Drug Store in the Chicago and Northwestern station.

During the robbery, a gunfight broke out. Two men were killed: Sam Manno and an elevator operator named Haskell Daniels. Another man named James H. Frawley was wounded during the gun battle.

One guy who was arrested at the scene, Tony Spranza, had identified two others as being part of the robbery: Joe (Belmonti) Mirrabella and Joseph Gallichio. Gallichio was a friend of Manno’s.

James Mirro in 1935.

Police had been looking for Gallichio when they raided an unnamed bar on the west side of Chicago in hopes of finding him. Instead, they found Mirro and brothers John, Rocco, and Paul Pelletier, along with a stash of guns.

Mirro and the others were held for questioning but released.

In November 1946, Mirro was picked up in a general police sweep at Colosimo's Restaurant at 2126 Wabash Avenue. Along with Mirro, Paul Labriola, whose police record included robberies and auto thefts, and a bartender named Frederick Herme were also picked up.

After posing for a lineup, they got their pictures in the paper and were released.

Frederick Herme, Paul Labriola, and James Mirro.

Full Speed Ahead

In July 1949, Mirro found himself in trouble again after cops busted up a three-car drag race on a Chicago street.

The police stopped all three cars at Ogden and Homan after they had raced through a stoplight. Future Outfit soldier Charles (Chuckie) English was in one car, Mirro and a female companion named Palm Alvey were in another, and three unidentified suspects were in the third car.

While cops talked to English, Mirro and the third car took off. The cops gave chase. They never caught the third car, but Mirro led the cops on a chase that reached speeds of almost 90 mph through residential neighborhoods before the cops finally caught up to him.

Charles (Chuckie) English

But Cowboy wasn’t giving up that easily. As cops tried pulling him out of his car, he started swinging until a taxi driver stumbled upon the scene and helped subdue Mirro.

Mirro was charged with drunk driving, resisting arrest, assault and battery on a policeman, disorderly conduct, and speeding. His friend, Palm Alvey, was charged with disorderly conduct. English was charged with speeding and passing a stoplight.

On December 12, 1952, he was one of 30 enjoying a night out at the Grand Club at 1958 Grand Ave. Police described the club as a “notorious hangout for criminals.” It was owned by Anthony (Tough Tony) Capezio, the overall gambling boss of Grand Ave., who wasn’t present on the day of the raid.

Lt. Joseph Morris of the Chicago Police’s Scotland Yard unit told reporters he believed “most of the crimes in Chicago have been hatched right there.”

The Grand Club

Others picked up with Mirro included Americo DePietto, future Outfit boss John DiFronzo, who was 23 at the time, and future Outfit soldier James D’Antonio, who was 24 at the time..

The cops had raided the club because cops had been apparently threatened that if they ever stuck their nost in the club, they would be beaten.

Nobody was beaten, and all arrested were questioned and later released.

Needle Nose

On March 17, 1954, Mirro was arrested along with a dozen other hoodlums, including Paul (The Waiter) Ricca and Anthony (Tough Tony) Capezio, for questioning in the gangland slayings of Paul (Needle Nose) Labriola and James (Jimmy the Jew) Weinberg. Their frozen bodies were found in the trunk of a car the week prior. They had been drugged and garrotted. ,

The two were apparently trying to set up a new tavern and restaurant association to rival the official Chicago Restaurant Association. Authorities also believed they were selling “protection” to bars without the Outfit’s permission.

Police pull Labriola's body out of the trunk.

Paul Labriola in better days.

Ricca had just been released on parole the week before their bodies were found. So, police were very interested in whether or not there was a connection.

Side note: Labriola’s murder was a big topic during the 1963 Kefauver hearings. It was believed that Labriola planned to shove Abraham Teitelbaum, who was head of the Chicago Restaurant Association at the time, out a window to eliminate the “competition.” Teitelbaum was also a former lawyer for Al Capone. Outfit member Marshall Caifano was accused of being one of the “ring leaders” in the movement to set up this new organization.

As it turns out, Labriola’s gang all met an unfortunate end. John Kowalski was killed in 1945. James Barsella was murdered in 1949. The last official member of Labriola’s gang, Emil (Grumpy) Grudecki, was shot to death in March 1955 as he was standing outside a bar after a night of drinking. A car saddled up, someone leaned out the window and shot him multiple times.

James Barsella

John Kowalski

Emil (Grumpy) Grudecki

The only member of the gang not to suffer a gangland-style death was Martin (the Ox) Ochs, who died in a hospital bed of natural causes in 1950.

Even Labriola’s close associate, Outfit enforcer John Miraglia, suffered a horrible fate. He was shot to death in August 1959.

Martin (the Ox) Ochs

John Miraglia

In January 1966, Labriola’s murder became front-page news again when Mirro and Mad Sam DeStefano were pulled in for questioning during a Chicago Crime Commission probe on the juice rackets.

Fred Ackerman, a disbarred lawyer turned informant, testified that Mirro had told him Needle Nose Labriola and Jimmy the Jew were killed because they took $80,000 from the bartender’s union and that DeStefano had ordered the murders.

Fred Ackerman leaves the hearings.

Mirro refused to answer any questions about Labriola’s murder or any questions asked at the hearing, pleading the 5th Amendment 89 times. DeStefano also refused to answer any questions, pleading the Fifth 370 times.

Mad Sam was never arrested for the murders.

Mad Sam and his wife at the hearings.

As a side note, Outfit members Fiore Buccieri, Jackie Cerone, and boss Tony Accardo were also subpoenaed to testify at the hearings.

Juice loan victims also testified and were hidden by a cloth curtain, and their voices were distorted to prevent their being identified by mobsters. Victims testified that they paid interest rates as high as 20 percent. They also claimed that borrowers were kidnapped and tortured if loan payments were late.

Side note: In October 1960, Joseph Nicoletti, a “former president of a gangster-dominated tavern association,” testified at Tony Accardo’s income tax trial. Not only did he claim he was Accardo’s close buddy for 13 years, but he also testified that without his “knowledge,” he was made president of a tavern association created by Labriola and Weinberg. He also testified that the two murdered hoodlums served as Accardo’s “bird dogs to sniff out new rackets for the mob.” There is no information on whether Joseph Nicoletti is related to informant and Outfit hitman Chuck Nicoletti.

High-Stakes Robbery

In January 1955, Mirro was sentenced to 3 years in federal prison for his part in an armed robbery at the home of Oscar U. Zerk, an inventor who lived in Kenosha, Wisconsin. More than $500,000 worth of art and other valuables were taken from Zerk’s home in February 1954. Zerk was tied up as the robbers looted his home.

Mirro pled guilty to charges of interstate shipment of stolen goods.

His old Outfit pal, Americo DePietto, was charged with him and sentenced to 4 1/2 years in federal prison. Zerk identified him as the leader in the robbery.

Americo DePietto

Another associate, Nick George Montos, pleaded guilty to possessing $150,000 of Zerk’s property and was sentenced to 7 years in prison. Both DePietto and Montos were sentenced in 1954.

Mirro’s sentencing was postponed for a year because authorities hoped to find the rest of Zerk’s property, which they believed Mirro had concealed. They weren’t able to recover any more of Zerk’s property.

Side note: Montos had a 20-year criminal record for robbery and thefts “studded” with escapes. He was also listed on the FBI’s 10 Most Wanted List for a year. At the time of his arrest for the Zerk robbery, he was wanted for criminal charges in Georgia and Florida.

Nick George Montos

In September 1964, he was indicted with 10 others for a gambling conspiracy indictment in connection with a policy wheel run by undercover police agents. Others indicted included Robert McDonnell, a state prosecutor turned defense lawyer, and Robert Hopkins, a suspended Chicago police detective.

James J. Gallagher, an agent for the Chicago Police Department and the Illinois Crime Investigating Commission, posed as a NY hoodlum and ran the policy wheel from April 21 to June 15. Mirro and the others did not know Gallagher was a cop.

The sting operation was abandoned after someone outed the sting operation. At the time, the three were released on $1,000 bond. They faced a $500 fine and up to a year in prison if convicted. No disposition on the case could be found.

In April 1965, IRS agents from the collection division seized his 1963 Cadillac, which had been locked in a garage near his home in Cicero.

The IRS had seized the car for failure to pay $5063 in income taxes withheld from employee paychecks at his North Avenue Steak House in Melrose Park from 1959 through 1961. The steakhouse burned down under “mysterious” circumstances in 1961.

Mirro's 1963 Cadillac

At the time, Mirro was facing criminal court for conspiracy to violate gambling laws. Mirro was also apparently in Florida when IRS agents seized his car, which was described as a “four-door limousine with such interior refinements as hi-fidelity radio sound.” The retail cost of that new Cadillac was about $5400.

In June 1966, he was sentenced to five years in prison for conspiracy to transport stolen money order blanks across state lines.

He was arrested in June 1965 and accused, along with four others, of stealing 14,700 blank American Express money orders from a Melrose Park supermarket in May 1961. Each money order had a potential value of $100.

Americo DePietto, Rocky Infelice, Frank Santucci, and Robert McDonnell, the same lawyer busted with Mirro in 1964, were also charged and convicted as part of the conspiracy. They were all sentenced to five years in federal prison.

Rocky Infelice

Frank Santucci

Fred Ackerman, who the group had tried to utilize to transport the money orders, turned informant and testified at their trial. He told jurors that Mirro was the “kingpin” of the operation.

Side note: In December 1968, newspapers reported that Mirro was at a Near Northside bar for a “going away” party for McDonnell. Johnny (Bananas) DeBiase and Nenos (King) Solomon joined the festivities.

Speed Demon

In September 1967, Mirro was arrested and charged (once again) with drunk driving, speeding, resisting arrest, and assaulting a police officer.

He was driving more than 80 mph on the Kennedy Expressway before he was pulled over. When the officer approached his car, Mirro took off again, leading cops in another high-speed chase through a residential neighborhood, just like he did back in 1949. Eventually, he was chased down but kicked the cop as he was arrested.

When he appeared in court in October to face the charges, he hid under a bench to avoid photographers. At the time, his lawyer, none other than his old buddy, Robert McDonnell, requested a jury trial. In November, he pleaded guilty to the charges and was fined $198. His driver’s license was also suspended.

Robert McDonnell

In February 1974, Mirror was caught openly discussing a new auto leasing racket with Joey Glimco, Marshall Caifano, and Joe Doves Aiuppa at a Melrose Park restaurant.

Aiuppa had just finished a relaxing steam bath at the nearby Luxor Baths at 2039 W. North Avenue when he joined his friends at the unnamed restaurant. But he stopped yapping after he noticed the busboy was hovering too close. As it turned out, the busboy was an undercover cop. The waiter was, too. Even the two men who appeared to be dozing near Aiuppa at the bathhouse as he was talking to friends were cops.

It’s not clear if anything came of this undercover operation.

James (Cowboy) Mirro

Mirro lived his life the same way he handled a getaway car -- full speed ahead, rules be damned. And considering how little time he spent behind bars, luck seemed to be riding shotgun. But no matter how fast you go, you can’t outrun the Grim Reaper -- though if anyone tried, it was Cowboy.

James (Cowboy) Mirro passed away on April 2, 1982, at the age of 69.

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