Operation Greylord was an investigation conducted jointly by the Federal Bureau of Investigation, the IRS Criminal Investigation Division, the U.S. Postal Inspection Service, the Chicago Police Internal Affairs Division and the Illinois State Police into corruption in the judiciary of Cook County, Illinois (the Chicago jurisdiction). The FBI named the investigation "Operation Greylord" because of all the judges having gray hair, although the national media reported it was named after the curly wigs worn by British judges.The 3 1/2-year undercover operation took place in the 1980s. The first listening device ever placed in a judge's chambers occurred in the undercover phase, when the narcotics court chambers of Judge Wayne Olson were bugged. In order to acquire evidence of corruption, agents obtained U.S. Department of Justice authorization to present false court cases for the undercover agents/lawyers to fix in front of the corrupt judges.
The first defendant to be found guilty was Harold Conn, the Deputy Traffic Court Clerk in the Cook County judicial system. Conn was convicted in March 1984 and was one of the many bagmen in the ring of corruption. The last conviction was that of Judge Thomas J. Maloney, who was indicted in 1991 on bribery charges and convicted in April 1993 of fixing three murder cases for more than $100,000 in bribes. Maloney was released from federal prison in 2008, and died the same year. A total of 92 people were indicted, including 17 judges, 48 lawyers, ten deputy sheriffs, eight policemen, eight court officials, and state legislator James DeLeo. Out of the 17 judges indicted in the trials, 15 were convicted. One judge, Richard LeFevour, was convicted on 59 counts of mail fraud, racketeering and income-tax violations, getting 12 years in prison. Ten years after the undercover case concluded, the historical investigations, prosecutions and trials concluded in 1994.
The systemic corruption lead to the formation of the Special Commission on the Administration of Justice in Cook County, a group assembled in August 1984 to examine the problems of the Cook County courts. The group also issued recommendations that were designed to contribute to a period of reform in the courts. The Commission wrote a total of 165 recommendations for the courts of Cook County. Operation Greylord lead to many other similar investigations targeting corruption in Cook County including Operation Silver Shovel, Incubator, Lantern, Operation Gambat, and Safebet. Operation Greylord was also a turning point in the use eavesdropping devices in order to obtain evidence for trial.
The key undercover FBI agents and lawyers were David Grossman, David Reis and Terrence Hake. Hake was a Cook County prosecutor, who complained about the bribery and corruption in the Murder and Sexual Assault preliminary hearing courtroom in Chicago. The FBI and United States Attorneys Office learned of his complaint and recruited him to pose as a corrupt prosecutor and later as a bribe-paying criminal defense attorney. While playing the role of a corrupt prosecutor, Hake supplied the evidentiary probable cause to bug Judge Olson's chambers. Lamar Jordan, David Benscoter, Marie Dyson, William C. Megary, and Robert Farmer were the principal FBI case agents and supervisors during the investigation. Cook County Judge Thaddeus Kowalski was important in the case due to his cooperation with authorities even though he knew his cooperation might endanger his career.
First Assistant United States Attorney Daniel Reidy and Assistant United States Attorneys (AUSA) Charles Sklarsky, Scott Lassar, Scott Mendeloff and Candace J. Fabri led many of the prosecutions. Four United States Attorneys, Thomas P. Sullivan, Dan K. Webb, Anton R. Valukas and Fred Foreman supervised the investigations and prosecutions. Valukus and AUSA James Schweitzer indicted 22 corrupt court personnel in 1985, along with Judge Raymond Sodini, who presided over the corruption in his courtroom at Chicago Police Headquarters.