The word gangster might invoke images of wannabe thugs showing off their toughness or bad boy persona. But in the face of real danger, some of these so-called gangsters might run for the hills. Real gangsters aren’t afraid of danger and they know the true definition of ruthless. Drugs, gambling, and prostitution are a gangster’s world. The ability to walk on the edge and create a lucrative income from organized crime requires some savvy business skills. Here are the top 10 business savvy gangsters who gave everybody “the business!”
1. Benjamin Seigel
Best known for running bootleg operations, illegal gambling rings, and being a vicious killer, “Bugsy” ironically had a conscious — something that’s lacking in many mobsters. His desire to run a legitimate business moved him to get involved with legal gambling companies in California. He partnered with business professionals and worked on several legit construction projects around Las Vegas and near Hoover Dam. But he couldn’t leave the bad boy life behind and was eventually gunned down by his enemies.
2. Al Capone
Started in street gangs at an early age. He move to Chicago during the Prohibition Era and viewed the banning of manufactured alcohol as his opportunity to capitalize. He was known for illegal gambling and prostitution. But while money and sex were at the top of every thug’s list during his day, Capone’s biggest paychecks came from the sale of illegal liquor.
3. Charlie “Lucky” Luciano
Built an empire around prostitution and he was one of the world’s best known heroin dealers. Intelligent and ruthless, his bootlegging operation eventually grossed $12 million a year. But with politicians and police officers on his payroll, Lucky saw far less profits as he had to pay these individuals in order to keep their mouth’s shut.
4. Meyer Lansky
Was good friends with Bugsy and Luciano and together the three formed Murder Inc. Lansky loved money, which made gambling a well-suited occupation for him. He invested in casinos and purchased an offshore bank — the perfect cover for his money laundering business. But Lansky’s friendship with Bugsy confirmed the notion that friends and money don’t mix, with Lansky reportedly ordering the murder of Bugsy.
5. Joseph Bonanno
Whoever said that a gangster couldn’t have a legitimate business had obviously never met Mr. Bonnano. A powerful businessman in New York City, he was best known for his funeral homes, factories, and clothing business. But here’s the gotcha: his funeral home was simply a clever means to hide the bodies of those who met his wrath.
6. Joseph Massino
Entered the business world with a legitimate lunch wagon truck. He bribed the competition with kickbacks to ensure the success of his business. However, peddling sandwiches to dock workers didn’t fulfill his underlying need for power and money, and Massino later became involved in truck hijacking. He and his partner would hijack trucks, sell the load, and then fudge their lunch wagon numbers to conceal their criminal acts.
7. Frank Costello
By the age of 13, Frank Costello had already associated himself with a local street gang and served time during his early years. He eventually lost his interest in street crimes, but considered it smarter to “use his brain to make money as a criminal.” This resulted in close relationships with crooked politicians, police officers, and judges. He could pay off officials, run his gambling and bootleg operations, and dodge jail time if caught.
8. Dutch Shultz
Realizing the profits he could earn from beer and liquor, Dutch Shultz established an illegal alcohol operation during the 1920’s. Everyone knew the danger of angering a gangster with control issues, and Shultz would occasionally lose this temper to subtly warn others of his ruthlessness. He worked with a local brewery, but considered it cost effective to buy a truck and deliver his own alcohol to buyers. But Shultz wasn’t seated behind the wheel. He sat in the back of the truck fully armed and ready to take out any hijacker with a death wish.
9. Paul Castellano
Was described as one of the “most powerful men in organized crime.” Despite the loan sharking, mob activity, and gambling rings, Castellano’s had a long-term goal of being a legit businessman. He ran a poultry company and a concrete pouring company. But once a mobster, always a mobster — the success of his businesses were primarily due to his mob connections.
10. John Gotti
Gangster mentality developed during his early teenage and adult years. His first job as a day laborer didn’t command much respect. Being told what to do didn’t set well with Gotti and he traded in the legit life for street gangs and mob families. He had his hand in several business ventures and owned a construction company. His annual sales were in the hundreds of millions of dollars. But before applauding him for escaping a life of crime, it’s important to note that a large percentage of his earnings were rooted in extortion, hijacking, loan sharking, and gambling.