Tommy Bilotti

The Most Hated Mobsters Of All Time

Vincent “Mad Dog” Coll

This may be the most hated mobster in American history. Mad Dog Coll was an Irish gangster from Hell’s Kitchen, New York, born in 1908. Coll was abandoned by his father and his mother died when he was very young. He became affiliated with the gangster lifestyle shortly afterwards. After a few stints in reform school, Coll was ready to step up his life of crime.

The young hoodlum got noticed by a big time Jewish bootlegger Arthur Flegenheimer aka Dutch Schultz. Dutch had a was in the market for a young enforcer to join his team. Mad Dog was doing contract murders while only is his mid teens. He prospered in the very dangerous bootlegging era, protecting Schultz’s many speakeasies and alcohol importing operations. 

The ambitious Mad Dog Coll quickly became a problem for Schultz, gaining in influence and territory. Coll was also ruthless, killing both men and women. He was arrested and put on trial for killing a speakeasy owner and a female hostess. In the last act of goodwill between the two men, Schultz used his influence to help Coll beat the double murder charges. 

Instead of being grateful, Coll decided to move in on Schultz’s territory shortly after. His crew hijacked Schultz’s liquor trucks and rob his speakeasies. Dutch put a $50,000 contract on Vincent and his brother Peter. It was 1930 and there were two major  wars in New York, the Castellammarese War and Mad Dog vs. Dutch Schultz. It was the most violent era in American mob history. 

Peter Coll was killed on 6/28/1931. Coll’s crew killed up to 20 of Dutch’s crew. On 7/28/1931, Coll was attempting a drive by shooting on team Schultz when four young children were caught in the crossfire. A five year old boy died from his injuries and Coll was now the biggest POS in the mob. Mobsters, police and civilians alike were on the hunt for Coll, and he was apprehended in October.

Mad Dog Coll went on trial again where he testified that he’d like to tear the throat out of whoever actually killed the child. Like before, Coll was once again able to beat the charge after witnesses fell off and the case came undone. The child killer was back on the streets and the war resumed. Coll soon took a contract from Salvatore Maranzano to kill Lucky Luciano on sight.

Before Coll could fulfill the contract, three of his crew were murdered on 2/1/1932. Just one week later, Coll himself was shot 15 times while inside of a phone booth. The killers paused to give Coll a scare and Coll’s eyes were wide open with fear. In a clear sign of his popularity, no mobsters and very few family members decided to show up to Coll’s funeral services. 

Joe “The Animal” Barboza

The name Joe Barboza brings back a lot of unpleasant memories to old time Boston residents. The Animal spent two decades shooting, stabbing and biting the faces of his many victims. These were people who borrowed too much money from the wrong guy. New England mafia boss Raymond Patriarca liked to use Barboza as a hitman and collector. 

Barboza was despised by most that knew him but the mere mention of his name brought fear to all in Boston. Even though he was Portugese, Joe just knew that one day he’d be the first non Italian inducted into the mafia. The mafia bosses, needless to say, did not feel the same way about the Animal. To them, he was simply a violent, hulkish goon that could do some dirty work. 

It’s estimated that Barboza killed more than 20 men during the late 1950s and 1960s. He was the one constant in the McLean/McLaughlin War that saw up to 60 men killed, a war that started over night of drinking gone wrong. It was Joe Barboza who kept the war going, he seemed to thrive in the atmosphere and certainly enjoyed seeing people suffer and die, which many did.  

When Joe went to jail on weapons charges in October 1966, he found out just exactly what Raymond Patriarca and the mafia bosses thought about him. His bail was set at $100,000 and he sent two crew members to go around to various mafia hangouts to pick up a “tribute” for Joe’s bail. The crew members were murdered and stuffed in the backseat of their car. A clear message.

Barboza was livid and decided to do something that no one expected, he became a government witness. Through his testimony, several mafiosi went to prison for the rest of their lives. Barboza disappeared into the Witness Protection Program with the entire Boston underworld looking for him. He was found in San Francisco in February 1976 and shot dead by a Boston mobster.

It later came out that Barboza made up most of his testimony and had convicted of murders they didn’t commit. This was a highly embarrassing revelation for the Boston FBI. They made a deal with the worst criminal in Boston to nab a bunch of guys who were nowhere near Barboza’s level, and they got duped. Barboza simply blamed a bunch of murders he committed on his mafia enemies. 

Tommy “The Toupee” Bilotti

The man that his enemies refer to as “Tommy the Toupee” became the underboss of the Gambino Family after the death of Neil Dellacroce in December 1985. Tommy Bilotti was the most disliked man in the Gambino Family. He lasted a full two weeks before he and Castellano were gunned down in front of Sparks Steak House in Manhattan. 

(Bilotti pictured at top)

John Gotti already was slowly planning the murder of Castellano before Dellacroe’s death. When Bilotti was named underboss, Gotti and most of the other Gambino captains were furious. No one in the family thought that Tommy had the skills or intelligence for the position, nor did he earn it in any way. He was a Castellano kneebreaker who Paul took a personal liking to. 

There was a deep talent pool for Castellano to choose an underboss. There was Gravano, Frank DeCicco, John Gotti, Jimmy Brown Failla and number of other qualified men in the family. Bilotti was looked at as a goon with a bad toupee by those guys. Killing Bilotti would now be mandatory if they were going to kill Paul. Bilotti being picked as underboss made it an easy decision. 

Bilotti was known for smashing enemies with baseball bats and metal pipes. He was referred to in the book Boss of Bosses as a “pitbull with shoes on”.Very few people with the exception of Big Paul actually like Bilotti and took him seriously. Bilotti took himself very serious and soon started to muscle in on other Gambino captain’s rackets and territories.

The FBI also took advantage of Bilotti’s lower intelligence with an out of the box plan. They intentionally interfered with the cable tv signal at Castellano’s mansion and Bilotti called demanding a technician come out to fix the problem. An undercover FBI agent fixed the tv and was able to install a listening device while Bilotti watched his every move. 

The FBI mission was pulled off perfectly but they would never have to face justice for it. On December 15, 1985, Bilotti and Castellano were assassinated in front of Sparks, sending shockwaves around the world. Bilotti’s less than two weeks as underboss may have been the most short and unceremonious ousting of an underboss ever. 

Jack “Legs” Diamond

John Diamond was born in 1897 in Philadelphia, Pennsylvania where he grew up until being drafted in World War l. Diamond did not last long and was eventually thrown in prison for deserting the army. In prison, he found his true calling, organized crime. He met many high level gangsters and was soon out again looking for action.

The young man called “Legs” for his ability to flee after a crime took to mob life like a fish in water. He was an enforcer for Arnold “The Brain” Rothstein during prohibition. He was a flashy character known for his fancy suits and flamboyant lifestyle. He employed ruthless tactics such as hijacking liquor trucks and torturing innocent drivers to get information on his enemy’s operations. 

After falling out with Rothstein, Legs went to work for Jacob “Little Augie” Orgen. He worked alongside Lepke Buchalter and Gurrah Shapiro, who were secretly planning to kill Orgen and take over his empire. In 1927, Legs and Orgen were ambushed, Diamond was injured but Orgen was killed. Lepke pacified Diamond afterwards by giving him a cut of the action. 

Diamond had no qualms about killing anybody, including innocent civilians. After murdering a rival in a crowded bar, he killed the bartender and three other unfortunate people who happened to be there. After this, Legs went into hiding. Dutch Schultz took over Diamond’s territory with the blessing of Luciano and the Syndicate bosses. 

It was a testament to the unpopularity of Diamond that the mafia would replace him with Schultz, a loose cannon they also hated and killed a few years later. Diamond and Schultz entered into a bloody war. It was at this time that Legs would become legendary for his ability to live for so long while being shot at and often hit on a regular basis. Schultz in private meetings with his men was in awe of the nine lives gangster he was up against. 

His enemies finally caught up with Legs, aka “The Clay Pigeon of the Underworld”. Diamond had been shot in three separate incidents between October 12, 1930 and December 18, 1931. This time his attackers broke into his apartment and one held Legs down while the other unloaded three shots into his head. There were so many people that wanted him killed and his death went unsolved.

Anthony “Tony” Mirra

The general public was made aware of Tony Mirra through the experiences of undercover FBI agent Joe Pistone, during his time posing as Donnie Brasco. Pistone said that Mirra was by far the nastiest most irrational mobster he had met in his 6 years undercover. Mirra was actually the man who originally brought Donnie Brasco into contact with the Bonanno family.

Tony was known for violent outbursts where he would assault underlings in public. Although he was a very unpopular guy, Mirra was a solid earner. This and his willingness to kill earned Mirra the status of a made man. He was making hundreds of thousands in drug trafficking, extortion and peddling in illegal pornography. He fled New York in 1977 after being nabbed for narcotics trafficking.

When Mirra returned a few years later, he was outraged to see that Lefty Ruggiero had become Brasco’s mafia mentor. He demanded that Brasco be returned back to his crew and even went to the Bonanno bosses about it.When he didn’t get his way, Mirra then suddenly accused Donnie Brasco of stealing $250,000. This was a very dangerous position for FBI agent Pistone. 

When it came to reputation, no one was more fierce than Mirra. He was well known to be a hitman with more than a dozen kills. He was also notorious for slashing many people with a knife that he always carried. He often just ripped off associates who were powerless to fight back. Pistone was able to avoid Mirra through the protection of Sonny Black Napolitano and Lefty.

After Donnie Brasco was outed as an FBI agent in 1981, Mirra knew he was in trouble. Napolitano was killed shortly after. Mirra knew that there were many people who would like to see him killed so he went into hiding. On February 18, 1982, Mirra went to meet two cousins, Joseph D”Amico and Richard Cantarella, not knowing that they had been given the contract to take him out. 

Even Mirra’s uncle Alfred Embarrato was in on the plot and fully agreed that Mirra had to go. After greeting his nephew Joey, Mirra got in the car with him to go for a drive and chat. Before he could turn his key in the ignition, Joey unloaded his gun into the side of Mirra’s head. The Bonannos were kicked off the Commission as punishment for the Donnie Brasco debacle.

Tony “The Ant” Spilotro

The most feared hitman ever from the Chicago Outfit was Tony “The Ant” Spilotro. When they wanted to protect their investments in Las Vegas, Spilotro was chosen for the job. Tony was the perfect guy for the situation. He was a vicious killer with more than 20 murders under his belt. No wanna be gangsters in Vegas were going to dare challenge him after he came to town. 

Tony earned his reputation in Chicago as a hitman under Outfit psychopath “Mad Sam” DeStefano. The crew was known for torturing their victims if they were an enemy or if they were looking for information. At least once they used a vice on one victim’s head until his eyes popped out. DeStefano and Spilotro would also use ice picks, a tactic used years earlier by Murder Inc. 

Eventually Mad Sam became a black eye to the Outfit and they had Spilotro kill his mentor. Despite resistance from some of the old timers, Spilotro was eventually promoted and became a made member of the Outfit. When the need for them to send someone out to Las Vegas to protect their investments arose, Tony the Ant was selected. 

Spilotro went out to Vegas and immediately put his own crew of burglars later known as the Hole in the Wall Gang. The gang quickly earned the attention of Las Vegas authorities, and they were able to tie Spilotro’s gang back to the Outfit in Chicago. Tony was also facing murder charges back in Chicago. The bosses decided to take no chances with Spilotro. 

To understand how the Outfit really felt about their long time enforcer, just look at how his execution was handled. Tony and his brother Michael were lured to a house where they were literally pummeled to death slowly. Before he was finished off, Tony was forced to watch the gruesome murder of Michael. 

The discipline could have been administered with a few bullets but clearly the bosses wanted to make it painful for Tony. He had tortured many others and faced a punishment similar to what he used to dish out. Ever the experienced killer, as he was being led to the basement Spilotro knew this was it as asked to say a prayer, which he did not get.