The Black Book of Ruby Stein: The Secrets Jimmy Coonan May Have Wanted Buried

In the underworld of 1960s and 1970s New York, money bought more than expensive suits, waterfront apartments and a table in the back of a Manhattan restaurant. It bought silence, loyalty, protection and access to people who preferred to conduct their business behind closed doors. For the men who operated outside the law, information could be every bit as valuable as cash, and sometimes considerably more dangerous.

Charles “Ruby” Stein understood that business better than most. He was a major loansharking financier with connections reaching into the criminal underworld’s upper levels. He knew who borrowed money, who was struggling to repay it, and who could be made to pay when the deadlines passed. Somewhere in the mythology surrounding his career emerged the story of a black book: a ledger of names, debts and secrets that may have been worth more than the money Stein lent.

Then Jimmy Coonan murdered him.

The question that continues to intrigue anyone studying the Westies is not simply why Coonan killed Stein. It is whether Stein possessed information that made him dangerous—and whether Coonan stood to gain something beyond eliminating a powerful creditor.

The Man Behind the Money

Before his name became associated with one of the Westies’ most notorious murders, Ruby Stein was already an established figure in New York’s criminal financial world. He worked alongside Nicholas “Jiggs” Forlano, a powerful loansharking figure whose business operated within a network of bookmakers, gamblers, businessmen and organized-crime associates.

Their reputations were not based on neighborhood gossip alone. A 1968 discussion in the Congressional Record specifically identified Stein and Forlano among New York City’s largest loan sharks, describing their connections to major Mafia figures. The congressional discussion also examined the flow of money through illegal lending operations, illustrating how criminal capital could move through apparently legitimate businesses while generating enormous profits.

This was not a small neighborhood operation. Stein occupied a position in a financial network where money could be advanced to one borrower, passed through another business and ultimately collected from someone who might never have known where the original capital came from. The system depended on secrecy, connections and the threat of consequences when a borrower failed to meet his obligations.

Stein was one of the men who helped keep that machine running.

The Business of Knowing Who Owed You

Loansharking was never simply a matter of handing someone an envelope of cash and waiting for repayment. A successful lender needed to understand the borrower’s business, income, associates, habits and vulnerabilities. A bookmaker who needed money to cover gambling losses was different from a contractor seeking capital to keep his operation afloat, but both could become profitable customers if the lender understood the risks.

That meant keeping records.

Names, amounts, repayment schedules, interest, collateral and business relationships were all part of the operation. A debt ledger could reveal much more than the amount someone owed. It could expose financial partnerships, criminal associations and the weaknesses of people who preferred to keep their private affairs away from public scrutiny.

In the underworld, a ledger could become a weapon.

The Senate’s 1968 discussions of organized loansharking described a hierarchy in which criminal capital moved through several levels of lenders before reaching individual borrowers. Interest rates could be extraordinary, and repayment was sometimes enforced through intimidation and violence. The person holding the debt records could therefore possess an unusually valuable collection of information about the people operating around him.

Stein’s business gave him access to precisely that kind of world. His customers were not necessarily ordinary people looking for a short-term loan. They could be gamblers, bookmakers, businessmen and criminals whose financial problems were best kept out of sight.

A loanshark who remembered every debt was useful. A loanshark who recorded every name could be dangerous.

The Black Book: Ledger or Legend?

The story of Ruby Stein’s black book is compelling because it seems to explain why a man with his connections could become such a dangerous liability. The image is almost cinematic: a worn leather ledger filled with names, amounts, secret arrangements and the financial obligations of people who could not afford to have their business exposed.

But there is a problem for researchers. The surviving federal appellate opinion concerning the Westies’ criminal enterprise does not establish the existence, contents or disappearance of a specific black book belonging to Stein.

That distinction matters. It is easy to imagine a ledger containing the names of bookmakers, businessmen, gangsters and politically connected figures. It is equally easy to imagine Jimmy Coonan taking possession of it after Stein’s murder. But imagination is not documentation, and those details should not be presented as proven facts without a reliable source.

What can be established is already significant. The 1991 Second Circuit decision in United States v. Coonan identifies Stein as a loansharking financier to whom Coonan owed a substantial amount of money. The court also confirms that Coonan and other Westies murdered and dismembered Stein in May 1977.

The court’s findings give us the essential pieces of the story: a powerful lender, a substantial debt, a violent borrower and a murder. The black book remains an unanswered question, but the documented financial relationship provides a compelling reason to investigate what records Stein maintained and what became of them.

Sometimes the unanswered question is more revealing than the legend.

Jimmy Coonan’s Problem

By the 1970s, Jimmy Coonan was building his position in Hell’s Kitchen. His organization was expanding through loansharking, gambling, extortion and other criminal activities, but building a criminal enterprise required capital. Money had to come from somewhere, and financial backing often carried obligations that could become dangerous.

Stein was part of that financial world.

The relationship became especially troublesome when Coonan owed him a substantial amount of money. A creditor with Mafia connections was not someone a young neighborhood gangster could simply ignore. Stein had standing in the criminal economy, and his financial relationships reached well beyond the streets of Hell’s Kitchen. Coonan was dealing with a man whose influence and connections could make him difficult to intimidate or dismiss.

He faced a choice familiar to the criminal underworld: repay the debt, negotiate a settlement or eliminate the creditor.

He chose the third option.

According to the federal court record, Coonan, William “Billie” Beattie and other Westies murdered and dismembered Stein in May 1977. It was an exceptionally brutal act, and it demonstrated how far Coonan was willing to go to protect his position. The man who had financed criminal activity and occupied a place in New York’s loansharking network was now dead at the hands of the younger gangster who owed him money.

The debt was no longer collectible, and the creditor could no longer demand payment. Whether Coonan also sought access to Stein’s financial records remains unproven, but the possibility gives the story another disturbing dimension.

What Happened to Stein’s Records?

If Stein maintained detailed records of his loans, what happened to them after his death? Were they recovered by investigators, passed to associates, destroyed or taken over by someone who wanted to inherit his financial operation? These are legitimate historical questions, especially considering the number of people who may have had an interest in the money Stein controlled.

The available appellate decision does not answer them. It establishes the murder and the financial relationship between Stein and Coonan, but it does not identify a recovered ledger or describe the fate of Stein’s business records.

Researchers looking for answers could examine the federal proceedings involving Stein and Forlano. One particularly useful source is United States v. Forlano, 358 F. Supp. 56 (S.D.N.Y. 1973), which involved Charles Rubin Stein, Nicholas Forlano and others charged with interstate wagering offenses. The case also addressed challenges to wiretap evidence used in the investigation.

The court record is valuable because it places Stein inside a documented criminal operation years before his murder. It offers a starting point for examining his associates, business relationships and the investigative attention directed toward his activities.

It does not, however, establish that investigators recovered a secret ledger containing the names of prominent underworld figures. Until such evidence emerges, the black book should be treated as an intriguing part of the story’s later mythology rather than a proven historical artifact.

The Mafia Connections Behind the Ledger

Stein’s importance becomes clearer when his business relationships are considered. The 1968 Congressional Record described him and Forlano as having connections to major Mafia figures and identified Stein as one of the sources of capital for an illegal lending operation involving other underworld financiers.

This was a network built around money, influence and mutual dependence. The people involved did not necessarily need to meet face-to-face to conduct business. One lender could provide capital to another, who could then distribute it to gamblers, bookmakers or businessmen. Money moved through layers of intermediaries, and each participant had an incentive to keep the operation quiet.

A man in Stein’s position could become an important financial link between people who might otherwise have no direct relationship. That made him valuable to the underworld, but it also made him vulnerable when disagreements arose over money, debts or control.

The more people who depended on a financial operator, the more complicated his death could become. Outstanding debts remained, accounts had to be settled, and associates wanted to know who would collect the money. Someone had to decide who inherited the business and who was left holding the losses.

Stein’s murder did not take place in a vacuum. It occurred inside a much larger criminal economy, where the disappearance of one financier could create opportunities for others.

The Murder That Changed the Westies

The murder of Ruby Stein was one of the defining episodes in the Westies’ rise. Coonan’s organization was becoming increasingly powerful in Hell’s Kitchen, and the killing demonstrated its willingness to use extraordinary violence against people who stood in its way. The federal prosecution that followed would eventually expose the gang’s involvement in loansharking, extortion, narcotics trafficking and other criminal activity.

The same Second Circuit decision describes the Westies’ eventual alliance with the Gambino crime family. The Gambinos provided financial support for the Westies’ loansharking operation and permitted them to use the family’s name and reputation in their criminal dealings. In return, the Westies paid the Gambinos a percentage of their proceeds.

That arrangement helped transform a neighborhood organization into a much more formidable criminal enterprise. Coonan had moved beyond simply controlling a few blocks of Hell’s Kitchen. He had established a relationship with one of New York’s most powerful Mafia families, creating opportunities that a small Irish street gang could never have accessed on its own.

Stein’s death belonged to the earlier chapter of that transformation, when Coonan was consolidating power and establishing the rules of his organization. The murder demonstrated that financial connections and Mafia associations did not necessarily guarantee protection from a determined rival.

The Ledger That May Never Be Found

The legend of Ruby Stein’s black book endures because it represents something larger than a missing notebook. It symbolizes the hidden architecture of organized crime: the debts, favors, financial arrangements and personal weaknesses that connected people who preferred to remain invisible.

A gangster’s gun could eliminate an enemy, but a ledger could expose an entire network. The names inside such a book, if it existed, might have been worth more than the cash Stein ever lent. They could have revealed who borrowed, who collected, who financed the operation and who depended on the arrangement to keep his own business alive.

Still, the historical record must be allowed to speak for itself. We know Stein was a major loansharking financier with important underworld connections. We know Coonan owed him a substantial amount of money, and we know that Coonan and his associates murdered him in May 1977. What we do not know from the available court records is whether Stein possessed the fabled black book, what it contained or what became of it.

Perhaps it was destroyed. Perhaps it passed into someone else’s hands. Perhaps the story grew out of the ordinary records every major loanshark needed to maintain. Until documentary evidence establishes otherwise, the mystery remains unresolved.

Whatever the answer, Ruby Stein’s real power was never just the cash he controlled. It was the network of people connected to it, and the knowledge that came with doing business in the shadows.

In Jimmy Coonan’s Hell’s Kitchen, that kind of knowledge could be more dangerous than a loaded gun. And when Stein’s debt came due, the man holding the ledger never got the chance to collect.

References:

1. United States Court of Appeals for the Second Circuit. United States v. Coonan, 938 F.2d 1553 (2d Cir. 1991). https://law.justia.com/cases/federal/appellate-courts/F2/938/1553/294303/
2. United States District Court for the Southern District of New York. United States v. Forlano, 358 F. Supp. 56 (S.D.N.Y. 1973). https://law.justia.com/cases/federal/district-courts/FSupp/358/56/1412407/
3. United States Congress. Congressional Record, 90th Cong., 2nd sess., January 30, 1968, pp. 1428–1431. Discussion of organized loansharking and the financial activities of Charles “Ruby” Stein and Nicholas “Jiggs” Forlano. https://www.govinfo.gov/content/pkg/GPO-CRECB-1968-pt2/pdf/GPO-CRECB-1968-pt2-1-2.pdf
4. United States Congress. Congressional Record, 90th Cong., 2nd sess., May 23, 1968. Senate discussion of the structure of organized loansharking and the role of lenders and enforcers. https://www.govinfo.gov/content/pkg/GPO-CRECB-1968-pt11/pdf/GPO-CRECB-1968-pt11-6-2.pdf
5. United States Department of Justice. Annual Report of the Attorney General of the United States, 1971. Washington, D.C.: U.S. Government Printing Office, 1971. https://www.govinfo.gov/content/pkg/GOVPUB-J-a081c87693ec0420a74d0988094f9e4d/html/GOVPUB-J-a081c87693ec0420a74d0988094f9e4d.htm
6. English, T. J. The Westies: Inside New York’s Irish Mob. New York: St. Martin’s Press, 1990.
7. English, T. J. Paddy Whacked: The Untold Story of the Irish American Gangster. New York: HarperCollins, 2005.
8. Capeci, Jerry. Murder Machine: A True Story of Murder, Madness, and the Mafia. New York: Dell Publishing, 1992.