Jimmy Coonan vs. the Five Families: The Irish Gangster Who Refused to Kneel

Jimmy Coonan did not become powerful by joining the Mafia.  He became powerful because the Mafia decided it was more useful to have him on its side.

That distinction matters.

By the late 1970s, Coonan controlled an Irish-American criminal organization rooted in Hell’s Kitchen. The Westies had their own gambling operations, loansharking business, labor connections and neighborhood muscle. They were not simply another crew waiting for orders from an Italian crime family.

Then Coonan encountered the larger machinery of the New York Mafia.

The relationship that followed was one of the strangest arrangements in the city’s underworld: an Irish gang maintaining its own identity while operating in partnership with the Gambino crime family.

Federal prosecutors later described the arrangement in unusually concrete terms. The Gambinos financed the Westies’ loansharking operation and allowed Coonan’s organization to use the Gambino name and reputation. In return, the Westies paid the Gambino family a percentage of proceeds from various criminal activities.

It was cooperation. It was also leverage. And for Jimmy Coonan, that distinction was everything.

Hell’s Kitchen Was Coonan’s Kingdom

Before the Gambinos entered the picture, Coonan had already fought for control of Hell’s Kitchen.

His enemy was Mickey Spillane, the older Irish gangster who had dominated much of the West Side through gambling, loansharking and neighborhood connections.

Coonan represented a younger, more violent generation.

He had challenged Spillane as a teenager, survived imprisonment and returned determined to take what he believed belonged to him. By the middle of the 1970s, the struggle had become a bloody contest for control of the neighborhood’s rackets.

The Washington Post’s contemporary review of T.J. English’s The Westies described Coonan and Mickey Featherstone as systematically consolidating Hell’s Kitchen’s lucrative criminal rackets through violence before linking up with the Gambino family.

The important point is that Coonan was already somebody when the Italians came knocking.

He had territory. He had soldiers. He had a reputation. And he had something the Mafia could use.

Why Didn’t the Mafia Simply Eliminate Him?

This is the question that makes the Coonan story interesting. If the Five Families possessed such enormous power, why tolerate an independent Irish gangster in the middle of Manhattan?

Because killing him was not necessarily the most profitable option.

The Westies controlled a neighborhood and possessed an intimate understanding of Hell’s Kitchen’s criminal economy. They knew the bars, bookmakers, loan-shark customers, union figures and street-level operators. They also had something an outside Mafia crew could not easily manufacture: local credibility.

The Westies could operate where outsiders might attract attention. They could collect. They could intimidate. And, when required, they could use violence. The Gambino relationship therefore turned Coonan from a potential obstacle into a useful asset.

The Second Circuit’s account of the Westies describes the organization as an ongoing criminal enterprise involved in loansharking, cocaine distribution and control of criminal activities around West Side piers. The court also noted that the Westies extorted jobs and payments from labor unions.

For the Gambinos, that was valuable real estate. Not Manhattan real estate in the conventional sense. Criminal real estate.

The Gambinos Needed Hell’s Kitchen

The West Side was changing rapidly. The old waterfront economy was declining, while redevelopment and construction were creating new sources of money. Construction sites meant contracts, labor, unions, no-show jobs and opportunities for kickbacks.

The Jacob K. Javits Convention Center became one of the major symbols of that transformation.

The construction boom was not merely about concrete and steel. Organized crime saw opportunities in the labor and contracting systems surrounding major projects.

That created a problem. Different Mafia interests wanted pieces of the same pie. The Westies already had muscle in Hell’s Kitchen.

The Gambinos had something larger: an established criminal network stretching beyond the neighborhood. Put the two together and the arrangement made practical sense. Coonan did not have to surrender Hell’s Kitchen.

The Gambinos did not have to invade it. They could divide the territory and the profits.

Roy DeMeo: The Man in the Middle

Roy DeMeo became the critical bridge. The Mob Museum notes that Coonan began meeting with DeMeo and Danny Grillo during the period when Coonan was consolidating control of the West Side. The relationship became one of the important developments in the Westies’ rise.

DeMeo understood the value of the Westies. He also understood the value of violence. That made him a natural intermediary between Coonan’s Irish organization and the Gambino hierarchy. The relationship eventually produced a remarkable arrangement.

The Westies remained the Westies. They did not suddenly become Italian. They did not abandon Hell’s Kitchen. Instead, they became affiliated with the Gambino organization while retaining their own criminal operation.

Federal appellate records later described the arrangement directly: the Gambinos financed the Westies’ loansharking operation and allowed them to use the Gambino name and reputation, while the Westies paid ten percent of proceeds from various illegal activities to the Gambino family.

That was not independence. But it was not ordinary subordination either. Coonan had negotiated something in between.

What Did Coonan Gain?

The answer was protection, financing and access. The Gambino name carried enormous weight in New York’s underworld. A small neighborhood gang could suddenly conduct business under the shadow of one of the country’s most powerful organized-crime families.

That changed negotiations. It changed collections. It changed threats. A Westie did not have to convince everybody that Coonan was dangerous. The Gambino connection helped do that for him.

The arrangement also provided financial resources. Federal prosecutors established that the Gambinos financed the Westies’ loansharking operation.

Coonan therefore gained something more valuable than a title. He gained infrastructure. The Irish street gang now had access to the machinery of a national criminal organization.

What Did the Gambinos Gain?

The answer was Hell’s Kitchen. But they also gained people willing to do dirty work. The Westies had a reputation for violence that had become legendary even before their alliance with the Gambinos.

They were neighborhood enforcers with little interest in appearing respectable. The Gambinos could maintain distance. The Westies could handle problems.

The arrangement also provided access to local rackets and labor relationships that were valuable in a rapidly changing Manhattan.

The federal case against Coonan’s organization eventually documented extensive criminal activity involving the West Side piers and labor unions. In one later episode, Coonan directed the killing of Vincent Leone, a Gambino associate involved in overseeing criminal activities on the piers, after Leone was accused of skimming money.

That episode reveals the complicated nature of the alliance. The Westies were working with the Gambinos. But they were still the Westies. And Coonan was still Coonan.

Coonan Was Not a Made Gambino

That distinction is easy to lose when the Westies’ history is told as a simple Mafia story. Coonan was never transformed into a traditional Italian-American Mafia boss. He remained the leader of an Irish-American criminal organization.

The Westies operated under their own name and retained their own internal structure. The federal court later described Coonan as the organization’s leader and Mickey Featherstone as his second-in-command.

That independence was both the source of Coonan’s power and the seed of future problems. He had entered a larger system without completely surrendering his own.

For a while, that arrangement worked. Then the people changed. The alliances changed. And the Westies’ violence became increasingly difficult to contain.

The Relationship Starts to Fracture

Coonan’s power did not last forever. He was imprisoned in 1980 on a gun-possession charge, while Featherstone was also incarcerated on a federal counterfeiting conviction. Yet the Westies’ gambling, loansharking and labor racketeering continued.

Then Roy DeMeo was murdered in January 1983. One of Coonan’s most important connections to the Gambino organization was gone. The relationship survived, but the personalities changed.

Daniel Marino became an important Gambino connection, and later Coonan dealt with John Gotti’s organization after Gotti’s rise following the murder of Paul Castellano in December 1985.

By then, however, the Westies were entering their final years. Federal investigators were closing in. The organization that had once seemed almost impossible to penetrate was beginning to unravel from inside.

The Westies Were Useful Until They Weren’t

That may be the most important lesson in the Coonan-Gambino relationship. The Mafia did not need to destroy the Westies because the Westies were useful. They provided something the larger organization could not easily obtain by simply sending an Italian crew into Hell’s Kitchen: local control.

The Westies knew the neighborhood. They knew the people. They understood its criminal  economy.  And they were willing to enforce their interests with extraordinary violence. But usefulness has a shelf life.

Once federal investigators began assembling evidence through informants, testimony and RICO prosecutions, the advantages of having an independent Irish gang operating on the West Side began to diminish.

The very structure that had made the Westies valuable also made them vulnerable. Too many people knew too much. Too many crimes had been committed. And too many relationships crossed organizational boundaries.

The Irish Gangster Who Wouldn’t Disappear

Jimmy Coonan’s story is not really about defeating the Five Families. He did not. Nor is it a simple story about an Irish gangster submitting to the Italian Mafia. He didn’t quite do that either.

Coonan found the narrow space between those two possibilities. He controlled Hell’s Kitchen first. Then he negotiated with a larger criminal organization from a position of local strength.

The Gambinos supplied money, reputation and connections. The Westies supplied territory, muscle and access. Everybody got something. For a while.

That was the genius—and the danger—of the arrangement. Coonan had discovered that survival in the New York underworld did not always require kneeling before a larger power.

Sometimes it required making yourself too useful to eliminate. But usefulness can become dependence. And dependence can become a trap.

By the time the Westies finally collapsed beneath federal prosecution, the old Hell’s Kitchen order had already begun disappearing. The neighborhood was changing. The waterfront was changing. The Mafia itself was changing.

Jimmy Coonan had managed something few neighborhood gangsters ever accomplished.

He forced one of New York’s major Mafia families to do business with him on terms that preserved the Westies as a distinct organization. But the price of doing business with the Mafia was that the Westies were no longer entirely their own. The Irish gang had entered the larger underworld.

And once it did, there was no going back.

References:

English, T. J. The Westies: Inside the Hell’s Kitchen Irish Mob. New York: G. P. Putnam’s Sons, 1990.

Quirk, Rory. “The Guts Gore of an Irish Gang.” The Washington Post, March 29, 1990. Review of T. J. English’s The Westies.

United States v. Coonan, 938 F.2d 1553 (2d Cir. 1991). United States Court of Appeals for the Second Circuit, July 16, 1991.

The Mob Museum. “In 1980s New York, the Mob had its hands in everything—even a museum.” The Mob Museum, 2024.

United Press International. “Federal jury convicts Westies gang members.” February 24, 1988.

National Crime & Gang Task Force. “Westies.” Historical overview of the Hell’s Kitchen Irish-American organized crime group and its relationship with the Gambino crime family.