James Coonan led the Westies, a gang based in Hell's Kitchen on the West Side of Manhattan. In February 1988 a federal jury in the Southern District of New York found that the gang was a criminal enterprise and convicted him, with six co-defendants, of racketeering and of a series of related offenses. The scheme the jury considered was described as covering eight murders, two attempted murders, one murder conspiracy, an assault and three kidnappings, carried out over some twenty years. Coonan received a total sentence of 75 years, the longest handed down in the case. The Second Circuit affirmed the convictions in 1989, and in July 2025 it ruled that he could not seek early release under the compassionate-release statute because his offenses pre-dated November 1, 1987.
The case is one of the large federal racketeering prosecutions of the 1980s. It rested heavily on the testimony of a former second-in-command of the gang who had pleaded guilty to a federal racketeering charge and agreed to cooperate. It also left a number of deaths that were charged only or attributed.
The Westies were an Irish-American gang rooted in Hell's Kitchen. They were active from the mid-1960s to the mid-1980s, earning money from loansharking, extortion, gambling, counterfeiting and narcotics, and using violence, including murder, to protect their position. In the government's description of the case, the gang controlled criminal activity in the neighborhood, and it also tried to extort money and jobs from unions that did business there.
In 1986 the Manhattan District Attorney, Robert Morgenthau, described the gang as linked to the Gambino crime family and used by it as hired guns. He said the gang was blamed for 28 murders, of which five had been solved, and that its membership had fallen from about 30 at its peak to between 10 and 15. Those figures are the prosecutor's own estimate and not a judicial finding.
Coonan was 39 when he was arrested in 1986. The prosecution's case was that he supervised the gang and received most of its criminal proceeds, and that loansharking proceeds were still being turned over to him in May and June 1986.
The proceedings against Coonan began in New York State court. In the summer of 1986 a warrant was issued after the gang's second-in-command, Francis "Mickey" Featherstone, was arrested for the 1985 murder of Michael Holly. Featherstone chose to cooperate with the authorities. He said that Coonan had arranged the Holly killing, and he linked the gang to dozens of murders since the mid-1970s.
On Wednesday, November 19, 1986, a New York State indictment charged Coonan with second-degree murder in the death of Patrick Dugan, who was 28 and had died in Manhattan in mid-November 1975. That evening FBI agents, alerted by the state authorities, arrested him in Ocean Township, New Jersey. At his arraignment in the U.S. District Court in Newark the next day he faced a federal charge of unlawful flight to avoid prosecution, and he was expected to consider waiving extradition so that he could face the murder charge in New York.
The government indicted Coonan and nine co-defendants on September 17, 1987. The charges included participating and conspiring to participate in a racketeering enterprise under 18 U.S.C. 1962. The trial in the Southern District of New York began in the autumn of 1987; it ran about five months in all, with a pause in December 1987 and January 1988 while counsel for one defendant was replaced.
Eight defendants were on trial together. In October 1987 a former member of the gang testified for the prosecution about the 1977 killing of Charles Stein, saying that he had taken part in it. A government informer gave evidence about the killing of Richard Tassiello. Featherstone was the principal accomplice witness. He was cross-examined for five days, and the jury was told to weigh his credibility with special care. The trial court excluded expert psychiatric evidence the defense offered about him, a ruling later upheld.
The jury, ten women and two men, deliberated for seven days before returning verdicts on Wednesday, February 24, 1988, before Judge Whitman Knapp. It first found that the Westies existed as a street gang, which the defense had denied, and that every defendant except one had taken part in a criminal enterprise through membership. It then found that the remaining defendants had taken part in a racketeering conspiracy, the most serious charge, which carried a 20-year maximum. One defendant was acquitted of all charges.
Coonan was convicted on ten charges and acquitted of tax evasion. His convictions were: participating in and conspiring to participate in the affairs of a racketeering enterprise; conspiracy to make extortionate extensions of credit and to use extortionate means to collect them; attempted murder and assault; conspiracy to commit murder; conspiracy to commit extortion against the Teamsters and the International Longshoremen's Association; conspiracy to evade income taxes; and financing extortionate extensions of credit.
Three of his co-defendants received long sentences. James McElroy, described as one of Coonan's chief enforcers, received 60 years. William Bokun received 50 years and Richard Ritter 40 years. Bokun and Ritter were also convicted of conspiracy to distribute cocaine.
In 1988 the district court imposed on Coonan 75 years' imprisonment and a $1 million fine. The Second Circuit later put the total at 75 years, including mandatory consecutive terms.
Michael Holly was 31 and died in Manhattan on April 25, 1985. The government's case was that Bokun admitted the killing in a recorded statement on May 18, 1986. Two other defendants were arraigned on a state murder charge for his death in August 1988.
Coonan, McElroy, Ritter, Bokun and one other defendant appealed together. On May 24, 1989 the Second Circuit affirmed the convictions in an unpublished opinion, and it denied rehearing on July 5, 1989. Petitions for certiorari were filed in September 1989 in the Supreme Court, and the Solicitor General's opposition followed in November 1989.
The court had rejected a series of arguments: that the hearsay exception for co-conspirators should not apply to a racketeering conspiracy; that the jury instruction on the link between the enterprise and the offenses was inadequate; that search warrants for one defendant's residence lacked probable cause; that one defendant should have been tried separately; that the exclusion of expert evidence on the informant was an error; that the questioning of one defense witness was improperly restricted; and that substitute counsel for Bokun had denied him his right to a lawyer.
Coonan has asked the U.S. Parole Commission for parole in 2012, 2021 and 2023, and it has not granted it. In December 2020 he asked the Bureau of Prisons to move for a reduction of his sentence; the Bureau refused, as it did his administrative appeal. In August 2023 he filed his own motion in the Southern District of New York. Judge Paul Gardephe denied it on June 26, 2024.
The Second Circuit heard the appeal on May 16, 2025 and decided it on July 9, 2025. The panel of Judges Lynch, Park and Robinson affirmed, in an opinion by Judge Robinson. It held that the compassionate-release provision does not apply to offenses committed before November 1, 1987, the date the Sentencing Reform Act of 1984 took effect, and that the First Step Act of 2018 did not change that limit. By then he had served about 38 years, and the Bureau of Prisons projected his mandatory release for June 1, 2030.
The Sentencing Reform Act of 1984 provides that its sentencing provisions apply only to offenses committed after the date it took effect. For offenses committed before November 1, 1987 the older system continues, in which prisoners are considered by the U.S. Parole Commission, not through the compassionate-release statute. Congress has repeatedly extended the Commission's existence to cover these cases, most recently to October 22, 2025, which the Second Circuit read as continued approval of the separate track. A bill in the 118th Congress that would have opened compassionate release to pre-1987 prisoners did not pass.
The racketeering statute under which Coonan was tried, 18 U.S.C. 1962, makes it an offense to take part in the affairs of an enterprise through a pattern of racketeering activity, and to conspire to do so. In this case the 1988 jury was first asked whether the Westies were an enterprise at all, and then whether each defendant had joined it.
The federal verdict was a finding of racketeering and conspiracy, not a separate murder verdict for each death in the scheme. The Dugan case was a state charge, separate from the federal trial. The government's case attributed the Holly killing to Bokun, and Featherstone's statement that Coonan arranged it is the account of a cooperating witness.
The Manhattan District Attorney's figure of 28 murders blamed on the gang is an estimate, and Featherstone's credibility was contested at trial, where the jury was told to examine his evidence with special care.
Mid-1960s: the Westies' racketeering activity begins.
Mid-November 1975: Patrick Dugan dies in Manhattan; Coonan is later charged with second-degree murder.
Summer 1986: a warrant is issued after the gang's second-in-command is arrested and begins to cooperate.
November 19, 1986: New York State indictment for second-degree murder; Coonan is arrested in Ocean Township, New Jersey.
September 17, 1987: federal indictment of Coonan and nine co-defendants.
Autumn 1987: trial begins in the Southern District of New York.
February 24, 1988: the jury returns its verdicts.
1988: Coonan is sentenced to a total of 75 years.
May 24, 1989: the Second Circuit affirms the convictions; rehearing is denied on July 5, 1989.
2012, 2021, 2023: parole requests; none granted.
December 2020: the Bureau of Prisons refuses to seek a sentence reduction.
June 26, 2024: motion for sentence reduction denied.
July 9, 2025: the Second Circuit affirms the denial.
June 1, 2030: projected mandatory release date.