Crime Library: Criminal Minds and Methods

Stone Upon Stone: Sing Sing Prison


Escapes from Sing Sing were rarely successful. Other prisons in New York experienced several bloody attempts, most of which ended in death for the convicts involved. Because of inhumane living conditions in these institutions, several inmate uprisings occurred during the 1920s. The most serious occurred on December 11, 1929, when several guards were killed in upstate Auburn prison during a riot. Eight convicts were shot and killed by guards before order was restored. That same year, a plot for a mass escape at Sing Sing was revealed when a prisoner informed on his fellow inmates. Several men had already dug a 40-foot tunnel that came within feet of the south wall. Working steadily and undetected for weeks, the escape team, led by inmate Roy Sloane, had carted away 50 cubic feet of dirt and dumped it unnoticed into the prison yard. The men were subsequently caught and later transferred to other institutions. But the most serious incident of escape at Sing Sing occurred on April 13, 1941.

Joseph "Whitey" Riordan, 26, Charles McGale, 45, and John "Patch" Waters, 30, all convicted of armed robbery, were being held in Sing Sing's hospital up on the third floor. At 2:30 a.m., they decided to make their move. Brandishing several revolvers which were smuggled into the prison a few days before, they shot prison guard John Hartye, 55, twice in the back as he made his rounds through the prison ward. Another convict patient, McGowan Miller, who had nothing to do with the escape plan, witnessed the killing and suffered a fatal heart attack on the spot. The desperate trio then fled to the basement of the hospital where they forced another prison guard to take them through a steam tunnel that led out to the village streets. Up on the ground level, accomplices parked a getaway car at a pre-arranged location. As Riordan and the others approached the car, two Ossining police officers, James Fagan and William Nelson came upon them by chance at the lower end of Main Street.

Correction Officer John Haryte, shot and killed by inmate
Correction Officer John Haryte,
shot and killed by inmate "Whitey"
Riordan. (Courtesy of Ossining
Historical Society)

The officers began to question the men. Suddenly, "Whitey" Riordan pulled out his revolver and started shooting. The others pulled out their weapons and also opened fire on the officers. Both cops fired back and a running gun battle ensued. Two bullets went through Waters' head. He was killed immediately. Officer Fagan was shot in the heart while Riordan and McGale managed to get away. Officer Nelson put Fagan in his police car and took the fatally wounded officer to the hospital where he was pronounced D.O.A. All law enforcement agencies in Westchester County were alerted to the jailbreak and the shootings. Over one hundred reporters and press photographers raced to the scene.

Meanwhile, Riordan and McGale ran over to the shores of the Hudson where they found a shad fisherman, Charles Rohr, getting ready to cast off for the day's fishing. The convicts drew their weapons and forced Rohr to take them across the Hudson to the Rockland County side. When they reached the opposite shore, the fugitives jumped from the boat and disappeared into the woods. However, within hours, Riordan and McGale were located by a pack of pursuing bloodhounds and taken into custody. Two outside accomplices, who smuggled the guns into the prison, were later identified and arrested.

A trial was held in White Plains County Court in June 1941 during which Riordan claimed that he was innocent and that the police beat his 63-page confession out of him. "We were handcuffed together," he said, "then they hit me. McGale was out on his feet but they kept on hitting him. Then a keeper started hitting me too!" One of the outside accomplices, William Wade, also claimed a confession was beaten out of him by cops who had hit him at least "1,400 times" during the interrogation. This included, he said, "300 kicks, 600 punches, being strung up by his hands 15 times, and knocked down 100 times."

The defendant's claims fell on deaf ears. Riordan and McGale were sentenced to death. Their accomplices in the bloody escape received life sentences at Sing Sing. On June 11, 1942, Riordan and McGale were executed in the death chamber, just yards away from where they shot and killed Correction Officer John Hartye. Riordan and McGale were numbers 475 and 476 on the parade of the condemned. The day had special irony for Riordan. It was his 28th birthday.