Roy DeMeo and Jimmy Coonan were two of the most violent mobsters in the history of New York City. Roy was a Gambino Family soldier in Brooklyn while Jimmy was the leader of the Westies in Hell’s Kitchen. Both were experienced in killing and even dismemberment. The joining of their forces in 1977 spread fear through the entire New York underworld.
Formation of Two Murderous Crews
While the west side Irish were causing trouble with the Italians who could crush them, the Italians would rather make a deal with them. There were various large construction projects going on in the neighborhood, including the Jacob Javits Convention Center, which would be a multi million dollar project on concrete alone.
The west side boss Mickey Spillane was a bit of a pain in the ass for the mafia. He was known for occasionally kidnapping mafia members and then holding them until a ransom was paid.It was a weird relationship because Spillane was also paying the mafia a tribute to operate. They basically tolerated Spillane for the time being.
Meanwhile, a young Irish gangster named Jimmy Coonan was making a name for himself in Hell’s Kitchen. Jimmy Coonan also had a major ax to grind with Spillane who had pistol whipped and held his accountant father for ransom. Young Jimmy was no accountant, he grew up to be a stone cold killer with a fierce reputation in the neighborhood saloons.
Another young tough guy in Hell’s Kitchen making noise was Francis “Mickey” Featherstone. He had shot and killed men in the neighborhood bars in front of witnesses multiple times and was able to beat the charges. During one of these shootings, he had borrowed a gun from Jimmy Coonan, who then recruited Mickey to become his number 2 guy.
Roy DeMeo was known as the man who did a large percentage of the Gambino Families’ dirty work. He was a full time hitman whose crew usually murdered at least one person a week.They operated out of the Gemini Lounge in the Canarsie section of Brooklyn. They were the most savage mafia crew since Murder Inc. was around back in the 1930s.
DeMeo also made the bosses tons of money by importing stolen luxury cars to Kuwait for a massive profit. But he was frustrated because he was still a lowly associate and not a made man. Roy knew Casellano wanted to expand the families’ influence on the west side. DeMeo had some connections to the west side. He reached out to them and was introduced to Coonan.
New Blood in Hell’s Kitchen
By the mid 1970s, Jimmy Coonan had essentially taken over the streets of Hell’s Kitchen. Mickey Spillane left the neighborhood for Queens and many of his old crew like Eddie “The Butcher” Cummiskey and Billy Beattie had switched to the Coonans side. Jimmy still wanted Spillane dead but now had bigger fish to fry.
Coonan saw an opportunity to make a lot of money if he killed a loan shark named Charles “Ruby” Stein and got his black book. It was a risky plan at best. Stein was well connected to the Genovese and Gambino families. Jimmy wasn’t phased by the risk at all. He was ready to do something that would shock even his own crew members.
On May 5,1977, Ruby was lured to Jimmy’s 596 Club. When the door closed, someone immediately hit the lock behind Stein while another man walked up and shot him in the head. Stein died quickly but the job wasn’t done. Jimmy ordered his team to drag Steins’ body to the club bathroom where they would dismember the body.
Billy Beattie and Mickey Featherstone were at the club for the Stein job. Both guys were experienced with violence and murders, but the experience of seeing Ruby Stein being taken apart was a nightmare. Coonan took way too much joy in their opinion. In Billy’s case, he owed Coonan a lot of money and was wondering if he might be next.
Roy knew the real story about Ruby Stein which should’ve been a death sentence for Coonan, but Roy took another stance. DeMeo had heard many stories about Jimmy Coonan and the brutality of the Westies.Roy’s crew member Danny Grillo was the connection between the two men. Roy was impressed with Jimmy and decided to recruit him and his west side crew.
The play Roy used to get Coonan’s loyalty was by killing the semi-retired Mickey Spillane. Roy killed Spillane outside of his home on May 13, 1977, just 8 days after the Westies killed Ruby Stein. In truth, the Italian mafia wanted Spillane dead for reasons unrelated to Coonan. It was the fight over the Javits Center construction profits. But it had the intended impact on Jimmy.
The Sitdown with Big Paul
Jimmy was ecstatic to be associated with Roy and the Gambino Family. He had big mafia dreams that went beyond the west side streets and Roy was his inroad to the top. It wasn’t long until Coonan needed Roy’s help. When Ruby Stein’s torso was found, suspicion fell on Coonan. Jimmy and his number 2 Mickey were called to sit down with Paul Castellano, the boss of the Gambino Family.
When Jimmy and Mickey got to Tomasso’s for the sitdown, Roy DeMeo greeted them. Roy calmly told them to just deny any involvement. That’s exactly what they did and it worked. Paul scolded them for their reckless behavior, but eventually told them that the Westies would now officially be associates of the Gambino Family.
Jimmy and Mickey were happy to walk out of that meeting alive. They had told their guys to be ready to go into Tomasso’s and be ready to kill everyone on sight if they hadn’t returned in 2 hours. That time came and went while Jimmy and Mickey were still in the restaurant but no one showed up. It turns out Billy Beattie and the boys got stoned and lost track of time.
Castellano charged Coonan 10% of Westies earnings that would go to the Gambinos. Coonan of course was happy with the deal but the rest of his crew, including Mickey were not. Mickey did not want to associate with the Italians. They were junior partners at best and had to adhere to all of Paul and Roy’s demands. Jimmy wasn’t entertaining any complaints from Mickey or the other guys.
There were some get-togethers with Roy DeMeo’s guys and the Westies in these days. Mickey met Joey Testa, Anthony Snter and Chris Rosenberg. In Murder Machine, it says that Mickey got into a heated argument with one of these men. After that incident, there was less interaction between the crews but the business deal was still in play.
With a new stream of income created and some new connections made, Roy was rewarded for the alliance by becoming a made man in the Gambinos. Paul Castellano had been resisting this for years because of his hesitancy about Roy, who he considered a street level thug. But Roy was not only handing up thousands every week, he also killed anyone Paul asked him to.
Downfall of DeMeo
The Westies were on a roll in the late 1970s. Jimmy and Mickey both beat a murder case, as did Jimmy McElroy. But by 1980, Coonan and Featherstone were both in prison for a few years. During this time, Coonan was still collecting the neighborhood rackets but Mickey was getting nothing. Jimmy also was still paying the Gambino Family their dues.
Both guys were released a few years later, but the dynamic changed. Jimmy had left the neighborhood and was now spending most of these days with the Italians. The disenchantment with Jimmy was growing with all of his guys. There were even a few conversations about killing Coonan but that was a scary job that was never taken.
As rough as things were in Hell’s Kitchen, it was much worse for Roy DeMeo and his crew. Roy’s international luxury car theft ring had been busted. Gambino boss Paul Castellano was indicted in the case which was serious trouble for Roy. By mid 1982 he was basically in hiding, knowing full well what happened to people in his situation.
In January 1983, Roy was called to a meeting by Nino Gaggi. When he got there, he was killed by his own men. Its’ thought that Joey and Anthony each put a bullet behind one of Roy’s ears as a symbolic gesture. DeMeo was such a dangerous guy that both John Gotti and Frank DeCicco had turned down the contract. Only his own crew were crazy enough to take the job.
Roy had been killing and dismembering his victims for a decade, even the NYC detectives of that era have said that his crew’s body count may have been 150-200 people. Danny Marino would step in as Jimmy Coonan’s Gambino Family contact. Mickey Featherstone was no fan of Marino and that only added to the tension in the Westies ranks.
End of the Coonan Era
Jimmy Coonan was so unpopular with his crew by the mid 1980s that they were actively looking to kill him for a while. In their opinion, he had completely sold out the neighborhood. Mickey, Billy, Jimmy McElroy and a group of the younger guys all agreed that Jimmy needed to go. They all agreed that Mickey should be the one who steps into his place of leadership.
Despite the plot, Jimmy was able to get McElroy and the young guns back under his wing. Featherstone turned down a murder request by Coonan. When that happened, Jimmy started plotting against Mickey. He had a Westies member named Billy Bokun put on a disguise and makeup to look like Mickey. It actually worked and Mickey was convicted of the murder!
Mickey soon found out that Jimmy was behind the hoax and he decided to get revenge. He made a deal with the government to testify against Coonan and the Westies on RICO and murder charges. Mickey was on the stand for four weeks and Coonan was convicted and sentenced to 75 years in prison. Featherstone’s murder conviction was overturned.
It was through Mickey Featherstone that the FBI learned the true extent of the Gambino and Westies alliance. They had always known there was a connection there having seen Coonan at some of the Gambino Families’ known hangouts. They tried to crack Coonan but Jimmy was not talking, but some other Westies were.
Jimmy McElroy was sentenced to 60 years in the same trial. A few years later he was desperate to get out of prison and also offered to make a deal. He had information that Gotti ordered a shooting of a union official named John O’Connor, which the Westies did. McElroy was not found credible and Gotti was acquitted in the assault trial.
Westies Help Rig Gotti Jury
While the relation between the Westies and Gambinos dissolved somewhat, the two groups would be reunited for something big. New Gambino boss John Gotti was on trial for racketeering in 1986. His bombastic but clever attorney Bruce Cutler put on quite a performance in court and received the credit for Gotti’s eventual acquittal, there was a more sinister reason.
At this time, the Westies were being led by Bosco Radonjich, a Serbian who had come to America in 1970. He was affiliated with an anti communist group known for various bombings. A friend of his named George Pape informed him that he was on the Gotti jury and willing to sell his vote to acquit Gotti for $60,000. Pape had lied about his mob ties during jury selection.
Boscoe immediately reached out to Sammy “The Bull” Gravano. Needless to say, the new Gambino leadership was thrilled with the help of their friends on the west side. Gravano and Gotti immediately agreed to the proposal and happily paid the $60,000 up front, knowing that the worst case scenario now would be a hung jury.
This was a massive victory for Gotti. He and his co defendants were all acquitted of murder, loansharking and armed hijacking charges. John was known in the press as “the Teflon Don” because none of the charges against him stuck. The FBI suspected foul play but was never able to put the pieces together until Sammy the Bull became a government witness in 1992.
Pape would be convicted of jury tampering in November 1992 and sentenced to three years in prison. Radonjich fled the U.S. that same year to avoid prosecution. He was brought back in 1999 to face the charges. Gravano was soon arrested and convicted in an ecstasy ring. He was the main witness, but now no longer a credible witness. Boscoe went free and fled the country again.
By the 1990s, Hell’s Kitchen had completely gentrified from a working class tough Irish neighborhood to a more expensive place where wealthier people flocked. The hardcore criminal element in the neighborhood was effectively dissolved with the change. The Westies who ruled the area for decades are now a distant memory. The Gambino Family is still very much active.