Near the end of his twenty-two-year career, Gerald Chapman’s several reputations came together in headlines touting him as a Spectacular Mail Bandit, Jail Breaker, and Criminal Extraordinaire. But above all, he was most often referred to as a “super-crook,” placing him beyond the level of most American criminals, one whose exploits were followed closely by the public. A worldwide manhunt finally resulted in his capture in 1925, but a decade earlier, he had done hard time at Clinton Prison.

Chapman, whose real name was believed to be George Chartres, or Charters, first ran into trouble in New York in 1908 and served a three-year stint in Sing Sing. After release, he was again arrested for grand larceny, and in January 1912 returned to Sing Sing, this time for ten years. As a brilliant criminal, and a handful to keep track of in any prison, he was sent north to the state’s most secure facility, Clinton Prison at Dannemora, where he quickly assumed a gang leadership position. As the source of many problems for guards and administration, he was finally relegated to an isolation cell, which at Clinton offered a very stark existence.

After several weeks of deprivation, he was given a job in the prison laundry, where he formulated an escape plan with other inmates. When their intent was discovered, Chapman was relegated to the prison’s dungeon — the infamous dark cell with no furnishings, cold and damp floors, no light, and very limited rations of bread and water — which eventually convinced him that serving time was the only way out. While he escaped many times during his criminal career, the walls of Dannemora held firm.

Shortly before his release in 1920, Chapman was transferred to Auburn Prison. Eighteen months later, he orchestrated a legendary theft, robbing a government mail truck in New York City by scouting a special shipment, boarding the truck while it was moving, and directing it to a side street, where his gang completed the robbery. The total take was a stunning $2.4 million (about $30 million in 2017).

He was caught several months later while living in luxury in New York City’s exclusive Grammercy Park. During questioning on an upper floor of the federal building, Chapman, a famous escape artist, disappeared. It was finally discovered that he had climbed out a window high above Broadway and crawled along a narrow ledge, planning to re-enter the building through another window and make his getaway. It almost worked, but he was spotted before getting back inside.

In August 1922, he was sentenced to twenty-five years in Atlanta’s federal penitentiary. Security was tight, but he escaped seven months later. He was caught after two days of freedom, but a month later he broke out again, setting off a nationwide manhunt led by some of the best trackers in the country.

Six months later, two criminals about to blow up a department-store safe in New Britain, Connecticut, were interrupted by Police Officer James Skelly. One of the thieves was caught, but the other shot Skelly and escaped. The officer died, and the shooter was identified as Gerald Chapman. For three more months he eluded the law, but was finally caught in Muncie, Indiana, and sent back to Atlanta.

Connecticut authorities eventually put him on trial for the murder of Skelly, and the jury arrived at a guilty verdict in less than an hour. He was sentenced to hang on June 25, 1925. It was widely reported that chief defense attorney Frederick Groehl, with tears in his eyes, reached for his client’s hand and said, “Chappie, I’m sorry.” With a squeeze of Groehl’s hand, Chapman replied, “Oh, that’s alright.” The two had become friends, of which Chapman had many. There was strong hope among them and his many admirers that executive clemency was in his future.

Appeals led to three stays of execution, in part because his attorneys argued that Chapman was a federal prisoner, and must serve his federal time before being released to Connecticut authorities for the death sentence. Expanding on that reasoning, prosecutors sought a federal pardon from President Calvin Coolidge, which he granted, removing the last major obstacle to Chapman’s execution. As a last-gasp effort, the defense argued that the pardon was unlawful because the prisoner hadn’t requested it. The Supreme Court disagreed, and Chapman was finally turned over to Connecticut prison officials.

No one had foreseen his colorful criminal career as a “gentleman bandit” terminating at the end of a rope, but a policeman had died and justice must be served. As he approached the death chamber on April 26, 1926, just minutes after his third reprieve expired, the phone remained silent, indicating that the governor had declined to intervene. Minutes later, Chapman, a famous alumnus of Clinton Prison, was executed.

Note: Most of the above was excerpted from the writer’s book Escape From Dannemora: 170 Years of Escapes, Tortures, and Infamous Inmates at New York’s Most Notorious Prison.

Photo: Gerald Chapman mugshot.