Mafia and The Mob Trivia

1. Born April 11, 1897, Mary Josephine Coughlin, known as 'Mae', had married what mobster and subsequently told their son many times, "not to do what your father did. He broke my heart." Who was her notorious gangster husband?

From Quiz Mob Wives and Mistresses

Answer: Al Capone

After three years of marriage, Mae had grown so fed up with Al's cheating on her that she dyed her hair bleach blonde to match Capone's current 15-year-old mistress's hair color. Apparently he had all his girlfriends dye their hair blonde.

From Quiz Mobsters and Their Fate

Answer: Murdered

Rothstein was born on January 19, 1882 in New York, New York. On November 4, 1928, he was shot during a meeting at the Park Central Hotel in Manhattan. He survived the initial shooting, but died two days later on November 6. Rothstein is famous amongst baseball fans as the mobster who paid the Chicago White Sox to lose the 1919 World Series. That event would come to be known as "The Black Sox" scandal.

From Quiz Nicknames Of Mob/Mafia Members

Answer: Teets

Sam "Teets" Battaglia signed on with Johnny Torrio and Al Capone when a gang war broke out with the Irish North Side Gang. Capone and Torrio were bosses at the time. Battaglia became a high ranking member of the mob by the late 1930s and was also a loan shark that you didn't want to fool around with. If you were merely behind in your payments to him, you would be ushered into the back room of a restaurant in Chicago named Casa Madrid. There you would face him and be either half or fully beaten to death. The nickname "Teets" came from one of those times a debtor was being beaten. Another mob guy who witnessed the savage thrashing of a debtor, had the nerve to question how Battaglia was handling the guy who owed him. Battaglia became angry and yelled at him. He screamed "Shaddup, or I'll bust ya in da teets!" By "teets" he obviously meant teeth. That's the story of how his nickname came about.

From Quiz Four Mafia Bosses to Remember

Answer: Albert Anastasia

An appropriate nickname for Anastasia, who was considered to be crazy by his fellow mob members. Gotti was known as the 'Teflon Don' for his penchant to escape conviction in court, despite his high profile actions and the strong evidence against him; and also as the 'Dapper Don' for his penchant for fancy dressing. Joe Bonanno was referred to as 'Joe Bananas', a take-off on his name that aptly described many of his actions.

From Quiz The Devious Minds of Organised Crime

Answer: Milk

In 1930, with Prohibition about to end, Capone needed a new source of income. Noting that the mark-up on milk was better than that on illegal booze, he kidnapped the president of the local Milk Wagon Drivers' Union. With the $50,000 ransom, he set up a rival business and, by using non-union drivers, undercut the other suppliers and soon had a monopoly. As Paul Lunde noted in 'Organized Crime: An Inside Guide To The World's Most Successful Industry'*, "Al Capone's Meadowmoor Dairies fixed the price of milk in Chicago and pioneered the concept of sell-by dates. It was a rare example of a gangland takeover that created a social benefit." (*Main source for this quiz).

From Quiz Global Organized Crime

Answer: The stealing of state and federal excise taxes.

Fuel racketeering is the rather mundane desire not to pay taxes, and the sometimes extraordinary lengths that people will go to avoid paying them. The origins of this lies in New York, among the Russian mob.

From Quiz Non-Italians in Organized Crime

Answer: Dutch Schultz

The "Dutchman", as he was also known, was a thorn in the Italian mafia's side. When Schultz decided he wanted New York prosecutor Thomas Dewey killed, the mafia--fearing unwanted publicity--had Schultz killed instead on October 23, 1935.

From Quiz Mafiosi and the Mob: Part 2

Answer: The Black Hand

They were known as The Black Hand, because when they sent extortion letters to businesses they would put a black hand on the paper. These Gangs terrorised shops and businesses in the Italian sectors of cities.

From Quiz Mafiosi and the Mob: Part 1

Answer: 7

By the time Capone was released he was so deranged from severe syphilis that he spent almost six months in hospital for treatment before being released. He died aged 48 on January 25th, 1947.

From Quiz Mafia Bosses

Answer: Philadelphia

Ratted out by members of his own gang, Nicky sits in the pen; as of May 2001, the remnants of the Philly mob face trial as former boss turned stool pigeon Ralph Natale does them in too.

From Quiz Mafia Nicknames

Answer: Scarface

Received scar in a bar fight. No one EVER called him that to his face.

From Quiz Mob Wives and Mistresses

Answer: Bugsy Siegel

You might not know it from the famous movie "Bugsy" in which Annette Bening played Virginia Hill to Warren Beatty's Bugsy Siegel, but Ms. Hill was something of a racketeer herself before, during and after her Siegel liaison. While working at Chicago's San Carlo Italian Village, she met Joe Epstein, Al Capone's bookmaker which led to her becoming a mistress, cash carrier, money launderer and spy for some of the era's leading racketeers. She laundered money at the horse track and lured men into placing bets on fixed boxing matches.

From Quiz Mobsters and Their Fate

Answer: Heart Attack/Stroke

Lucky was born on November 11, 1897 in Sicily, Italy. Luciano passed away from a heart attack on January 26, 1962 while walking through the Naples International Airport with American movie producer Martin Gosch. Gosch was in Italy to discuss Luciano's life for a movie he was producing about him. Unbeknownst to Luciano, Italian drug agents were following him with the intent of arresting him on drug smuggling charges. Lucky had been deported to Italy in 1946. Thomas Dewey commuted Luciano's 30-50 year sentence and had him deported to Italy because he had helped the U.S. Navy during WWII against Italy.

From Quiz Nicknames Of Mob/Mafia Members

Answer: The Grim Reaper

Greg "The Grim Reaper" Scarpa was a capo (captain) for the Colombo crime family out of New York. Unbeknownst to the family, Scarpa was at one time also an FBI informant. From the 1970s to 1980s, he was the chief enforcer for Carmine Persico who was a boss for the Colombo family. In 1991 it was known that Scarpa was responsible for three murders at the minimum. He was a powerful, slick, and brutal man which earned him his nickname. Another reason was that he would actually leave the number "666' on the pagers of people that he killed. The number "666" is known as "The Number Of The Beast" according to the bible.

From Quiz Mafiosi and the Mob: Part 3

Answer: Vincent Mangano

Vincent Mangano became boss of his family in 1931 after the Castellammerse war. He led his family until 1951. His family, beside being involved in countless illegal activities, quickly came to dominate the Brooklyn docks and, along with Frank Costello, took over the private garbage-carting companies in New York. Mangano disapeared in 1951 presumably murdered by his psychopathic under boss Albert Anastasia. Anastasia would in turn be murdered in 1957, leading to the rise of Carlo Gambino.

From Quiz Four Mafia Bosses to Remember

Answer: Joe Colombo

Two decades before Gotti paraded around in Armani suits, Joe Colombo was known for wearing $1000.00 outfits in the late 1960's and early 1970's. He would change clothes several times during the day, and kept an apartment just for that purpose.

From Quiz The Devious Minds of Organised Crime

Answer: Sabini

The five Sabini brothers were of half Scottish-half Italian descent. They dominated organised crime in London between 1918 and 1939, often fighting bloody battles with rivals. As well as running nightclubs, gambling dens and protection rackets, the Sabinis were behind the theft of gold bullion from Croydon airport in March 1936.

From Quiz Global Organized Crime

Answer: 1949

Pablo Escobar was the ruthless kingpin of the Medellin drug cartel. He was killed in the early 1990's in a hail of bullets by Colombian police. U.S. authorities helped out in this by tracing a long phone call he had made to his wife.

From Quiz Mafiosi and the Mob: Part 2

Answer: 1929

The St Valentine's Day massacre was the culmination of a bitter gang war that had ravaged Chicago for years. It was between Al Capone's gang and an Irish gang under Bugs Moran. The massacre itself occurred when four of Capone's men, two of whom were disguised as police officers, burst into one of Moran's warehouses and killed seven of Moran's men on February 14, 1929.

From Quiz Mafiosi and the Mob: Part 1

Answer: Jim Colosimo

Colosimo was primarily involved in brothel-keeping in Chicago along with Torrio until he decided not to get involved with bootlegging. Torrio, realising the potential fortune to be made, sent a hood by the name of Al Capone to kill him, which he did, leaving Torrio and Capone in charge of Colisimo's empire.

From Quiz Mafia Bosses

Answer: Luchesse

Now the former canary has his own website. What's this world comin' to?

From Quiz Mob Wives and Mistresses

Answer: Sam Giancana

Frank Sinatra was the one who introduced Judith to a JFK while he was a Massachusetts senator campaigning for the presidency. Sinatra also introduced her to a businessman named Sam Flood, aka gangster Sam Giancana.

From Quiz Mobsters and Their Fate

Answer: Cancer

Gotti was born on October 27, 1940 in The Bronx, New York City. In 1998, Gotti was diagnosed with throat cancer. The tumor was removed, but the cancer returned two years later. He passed away on June 10, 2002. Gotti was serving a life sentence without the possibility of parole for five murders, conspiracy to murder, loansharking, illegal gambling, obstruction of justice, bribery, and tax evasion. It took the jury 14 hours to find him guilty of all charges. After his guilty verdict, the FBI director in New York City told the press: "Teflon Don is gone. The don is covered with Velcro. All the charges stuck."

From Quiz Nicknames Of Mob/Mafia Members

Answer: The Waiter

Paul "The Waiter" Ricca was born in Naples, Italy in 1915. He murdered Emilio Parrillo there and was sentenced to only two years in prison. Vincenzo Capasso, who was from Sicily, saw Ricca kill the guy and ratted him out. Then he foolishly testified against him in court. Later on Ricca killed Capasso. He then found it necessary to change his name. He decided on Paolo Maglio and left Naples for Apricena, Italy. From there he managed to get to France where he got on a boat and headed for New York via Cuba. In Cuba he met Joseph "Diamond Joe" Esposito who was a bootlegger and also owned a Chicago restaurant. Ricca became maitre d'hote at Esposito's restaurant and that's how he became known as "The Waiter" but he hated his nickname. Paul was a puzzle to those around him. He was a heartless and cold killer yet he never cursed, appeared to be somewhat educated, and had incredibly good manners. If he told a story it was always clean without vulgarity. Paul even appeared to be sensitive and would cry when he heard about a fellow mobster's wife having a baby. Paul had a lot of money so he was able to fit in with the upper crust of society if he wished to. In an article written about him By John William Tuohy it was said that "Ricca was able to slip in and out of Chicago's elite society "like cashmere around a leper".

From Quiz Mafiosi and the Mob: Part 3

Answer: Wales

Murray 'The Hump' Humphrey's is a very unusual individual in the history of the mafia. He is the only significant Welsh gangster to be involved with the mafia. Due to the Chicago outfit allowing non-Italians to join and his incredible intelligence, he quickly rose to the top in the 1930s along with Tony Accardo, Paul Ricca and Johhnny Rosselli. They helped make the Chicago outfit massively powerful from Hollywood to Washington. Murray Humprey's was the brain's behind many of their money making schemes. Nicknames given to him by his associates included 'Mr Einstein' and 'The Brainy Hood'. Al Capone reportedly described how "Anybody can use a gun. 'The Hump' can shoot if he has to, but he likes to negotiate with cash when he can." Murray shied away from attention and advised his associated to do the same.

From Quiz Four Mafia Bosses to Remember

Answer: Joe Bonanno

All evidence points to Bonanna faking his own kidnapping the night before he was scheduled to go before a grand jury. Despite his being at odds with the other New York bosses, who wanted to oust him from power, he was out with no bodyguards and the alleged kidnappers left a living witness at the scene. Wiretaps revealed that the other families knew nothing about a kidnapping, and his own underboss was heard to state that Bonanna did it to avoid indictments or contempt charges from the grand jury. Joe Columbo, as an underboss of the then named Profaci family, was one of five members kidnapped by a rival faction led by Crazy Joey Gallo. He earned the respect of his kidnappers when, as they were being initially abusive, he demanded that they treat he and the others with respect. If they had to shoot them, fine, but until then they were to be treated like men.

From Quiz The Devious Minds of Organised Crime

Answer: The Forty Thieves

The Forty Thieves were a structured gang of shoplifters operating in South London. They worked in pairs and groups to raid the capital's stores. Admission to the gang only came on the death or marriage of an existing member.

From Quiz Global Organized Crime

Answer: Thieves in Law

The top thieves or "Vory" are portrayed as "Godfather" like figures. They trace their roots to the Soviet prison system that was established by Joseph Stalin in the 1930's. They maintain their own rules and reject involvement with the legitimate world.

From Quiz Non-Italians in Organized Crime

Answer: Meyer Lansky

Born Majer Suchowliñski, Meyer Lansky was the man that gangsters turned to for money laundering and Swiss bank accounts. He lived to the unheard of (for gangsters, that is) age of 80 years old.

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Last Updated Oct 11 2025 11:03 AM

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