Getting away with something feels pretty good, but most of us can’t imagine pulling off something “big” and getting away with it for fear of getting caught. What if you ran an empire, and each day was about avoiding the law and you succeeded? This group of “bosses” ran their crews and for the most part avoided getting busted.
This list details the very best (or worst) of gangsters responsible for the biggest heists, running city-wide organized crime syndicates and murder. Not all avoided the law their whole life, but let’s face it – if you made it 40 years killing people as a cost of doing business for a living and get busted for taxes, you beat the system.
In looking at this group, all ran organizations full of drug runners, prostitution, illegal gambling, murder or all the above. Sure, there may be a couple that weren’t the top boss, but let’s face it – we all have bosses. What these individuals did was distance them properly from any actual connection and kept those close to them from being “rats.” That’s good advice for anyone looking to run a business of any kind.
An honorable mention goes to Meyer Lansky, the gangster who kept a low profile as well as made sure he was never “boss,” not wanting the “public enemy number one” tag that comes along with running a crew. He was one of the smartest, earning over $400 million for the mob in his career, but never close to being considered a boss. Modesty: Another good trait for anyone looking to be big in business.
Here we go with a list of ten of the biggest mob crime figures to avoid the law.
10 George “Bugs” Moran
One of the North Side gang leaders, Moran was Al Capone’s nemesis and most law enforcement officials just assumed that would “take care of him.” They were wrong as Moran led bootlegging and other gambling activities for many years. A street smart brawler, Moran outwitted his competition on the streets. A lot of his career is debated as much of his time spent during his thirties and forties is undocumented. Late in his career he would eventually serve time for bank robberies, before dying of lung cancer. Moran outlived Al Capone, which was during the height of prohibition a bet no one would ever take.
9 John Gotti
Of course anyone with the nickname “Teflon Don” would have a big ego, and egos didn’t get much bigger than Gotti's. After serving four years on a murder charge, Gotti got put in charge of the New York Gambino crime family. This was during a time when the city was cracking down and it was difficult to run a gang. Still, Gotti was successful (hence the nickname) at operating his illegal organization for many years before being brought down. Eventually he did get convicted, but that was after many successful years and only because Sammy “The Bull” Gravano turned rat. Gotti was maybe the last old-school boss who walked the streets of New York as a proud (and known) mob boss. He died in prison of lung cancer in 2002.
8 Tony “Big Tuna” Accardo
For Accardo, taking over for a legend like Al Capone had to be difficult, especially after starting off as a hit man for Capone’s crew. Accardo’s claim to fame (or infamy) is his alleged involvement as a shooter/fake policeman in the Valentine’s Day Massacre. After Capone went away for tax evasion it was Accardo who was given the task of running a crew and managing all gambling operations. Despite this title, being looked at for a number of other murders (in addition to the St. Valentine’s Day Massacre) and being placed on the crime commissioners top ten most wanted list, Accardo denied being part of the mob. Accardo was never incarcerated. He denied his involvement for his entire life, he eventually died in 1992.
7 Whitey Bulger
A legend in South Boston, Bulger was a unique case due to the fact that not only did he run a gang, he was also an FBI informant. He mostly used this status to his advantage, bringing down other gangs to better his own and when the feds came looking for him he fled. Instantly he hit the Ten Most Wanted list, wanted for 19 murders, drug dealing and other racketeering charges. Rumors had Bulger in South America and Mexico, but it turned out he was just hanging out in West Hollywood, where as an old man, he was captured in 2011.
6 Sergei Tsapok
Tsapok led his group and was responsible for many murders in Russia before even hitting the radar. It took popping twelve people (four children) before officials even started looking at Tsapok. As the leader of an empire (after his brother was murdered) Tsapok terrorized the providence of Kushchevskaya. He was a cold blooded murderer that bribed officials with money and fancy cars. He murdered many and then got greedy, deciding to avenge his brother’s death, leading Vladimir Putin to take notice. Unfortunately for Tsapok, Putin already owned several luxury vehicles. In 2013 he was finally sent to prison, after a long life of getting away with murder. How he died inside is still suspicious (reported acute heart failure), some think it may have been a hit ordered from the top of Russia.
5 Semion Mogilevich
Known as the “boss of bosses” of the Russian Mafia, Mogilevich is both brainy (known as “The Brainy Don” and a multi-millionaire (for schemes involving immigration property sales). In the early seventies he did a couple of sentences for counterfeiting, but that turned out to be school and preparation for his life of crime. He used his millions to invest in prostitution, drugs and shady off-shore companies. These businesses required hands-on intervention where it’s not clear how hands-on Mogilevich ever got. What is known is that he was caught for tax evasion in 2008 and then fled in 2009, placing him on the FBI’s Top Ten Most Wanted list.
4 Hisayuki Machii
Machii should teach a class on how to be a mobster. After moving to Tokyo, Machii took control of prostitution and anything else that the Korean could exploit based on his connections between Japan and South Korea. Any shady work that needed to get done was probably ordered by Machii, but you would never know because there wasn’t any trail back to him. Few investigations even made it to him, instead stalling or leading to a dead end. Machii would go on to lead two organizations, make millions of dollars and then retire in the eighties. Machii died in 2002.
3 Charlie “Lucky” Luciano
Luciano was a business man at heart. How he conducted business (murder and threats) may not have been conventional, but was rather effective. Luciano created the American mob, breaking the ties from Sicily and uniting the families across the US. He kept smart people close (Meyer Lansky to name one) and kept the skeptics even closer (Al Capone) using respect and smoothing over when necessary. Luciano ran his crew like a business and expanded to the organization to be effective across state borders without a blood bath each time someone stepped over state lines. Luciano was on the radar of the FBI early in his career, was connected to everyone “big” during the twenties and never did serious time.
2 Al Capone
Known as “Scarface”, Capone needs no introduction. As public enemy number one, Capone was on the radar or payroll of every law enforcement agency from the local police through the FBI. Based in Chicago, Capone was the king of the twenties and thirties due to prohibition and his control over alcohol. What makes Capone an interesting case is how he threw his lifestyle in the faces of everyone. He was one of the first gangsters to flaunt the lavish lifestyle of a criminal. Despite this and a special federal task force assigned to bring him down, they never got him on any racketeering or organized crime related activities. Instead, late in his life it was tax evasion that brought him down and not a bullet, but syphilis that eventually killed him.
1 Pablo Escobar
Escobar was the well known Columbian drug lord, leader of the Medellin Cartel. He was the top man in one of the most dangerous gangs ever. Essentially, Escobar controlled drugs all around the world. He made billions and billions of dollars and killed thousands. Escobar was part of political parties and controlled all areas of the Columbian government. No one would dare go against Escobar for fear of not only being killed, but having their families killed with no repercussions. When challenged, Escobar would give his challengers a choice of “money” or “lead.” He got started in the sixties, ruled the drug industry in the seventies and eighties and was eventually shot and killed after a long career in 1993.