The Greenpointer Who Led a Prison Break from Sing-Sing

For years his wanted poster had hung in the Meserole Avenue Police station, but there was not a trace of Charles Bergstrom to be found. Bergstrom was wanted for being an accomplice in the worst prison break in Sing Sing history. He had become a wanted man for helping three of his buddies to break out of the maximum-security prison, and four people had lost their lives as a result of the breakout.

Bergstrom, who had been a longshoreman on the Greenpoint waterfront, had also spent a lot of time in prison. He had been arrested eleven times and served five prison sentences. His crimes, stretching back twenty years, included rape, robbery and carrying concealed weapons. In 1930, he was sentenced to Sing Sing where he befriended Joseph Riordan, Charles McHale and John Walters. When he left prison, he stayed in contact with the escapees who had formulated a plan to bust out. There were two other accomplices who had also participated in the nine month plan. Over months, the prisoners had loosened gratings in tunnels, fabricated keys and assembled guns—thanks to Bergstrom and the other accomplices who had smuggled the necessary material in a milk truck that visited the prison.

On April 14th, 1941 Bergstrom headed from Greenpoint to the prison in Ossining in a stolen car with a machine gun in the back seat. The prisoners had faked illness so that they could gain entrance to the prison hospital. Inside the hospital they shot and killed a prison guard and then escaped. The prison break was detected and the fugitives ended up in a gun battle with the Ossining Police that killed one of the police officers. The escapees were apprehended, and two of them died in the electric chair. Bergstrom escaped, but his role in the escape was discovered.

The police searched for Bergstrom for years, but he eluded them by joining the Air Force and serving four years in Europe. He should have known better than return to Greenpoint, but he wanted to visit his ex-wife who lived in their apartment at 151 Green Street. Clearly, she was frightened by Bergstrom’s return on July 30, 1945. Patrolmen driving down Green Street heard her screams from the fire escape. She told them that Bergstrom had returned and had broken a window to gain entrance to the apartment.

The police then arrested Bergstrom who denied his true identity, claiming that he was private James Ryan of the Air Force. Ryan had served heroically in the ninth Air Force, fighting in six major battles. After eight hours of interrogation, Bergstrom broke down and admitted his true identity. He pled guilty to aiding the escapees and was sentenced to seven years in prison.