9 Inmates of Sing Sing

George Washington Appo was a pickpocket and fraudster whose manner of speech in a testimony became influential in depictions of criminals. George himself wrote an autobiography, unpublished, and became the subject of a book. His father was a criminally insane Chinese American called "Quimbo Appo", Chinese name "Lee Ah Bow", while his mother, Catherine Fitzpatrick, was an Irish American. The origins of this criminal led a Louis Beck to present Appo as a story warning against "miscegenation". Appo served time in various New York penitentiaries including Sing Sing, the Blackwell's Island Penitentiary, and the upstate penitentiary in Dennamora. In a biography by Timothy Gilfoyle, the prison system of New York in the later half of the 19th century is depicted as being based upon the spoils system and largely corrupt. In the description of Sing Sing, Gilfoyle outlines the stove manufacturing operation the inmates were forced to endure. Gilfoyle describes the penitentiary at Blackwell's Island as having lax security, with inmates commonly escaping if they knew how to swim. Appo was also involved in a green goods scam in Poughkeepsie at one point in his life.

Charles E. Chapin was a New York editor of Joseph Pulitzer’s Evening World. He was convicted of the murder of his wife and sentenced to a 20-year-to-life term in Sing Sing prison.

Monroe Edwards was an American slave trader, forger, and criminal who was the subject of a well-publicized trial and conviction in 1842. Originally from Kentucky, Edwards moved to New Orleans then settled in Texas. He smuggled slaves into Brazil in 1832 and used the proceeds to purchase land in Texas. In 1836, he was again smuggling slaves, this time into Texas. After attempting to swindle his partner out of the profits of the venture, partly with forged documents, Edwards was forced to flee the Republic of Texas to the United States. He then tried to scam money out of various abolitionists in the United States and the United Kingdom, partly with forged letters of introduction. He traveled to the United Kingdom, but his schemes were mainly unsuccessful and he returned to the United States in mid-1841.

Raymond Martinez Fernandez and Martha Jule Beck were an American serial killer couple. They were convicted of one murder, are known to have committed two more, and were suspected of having killed up to 20 victims during a spree between 1947 and 1949.

Albert T. Patrick was a lawyer who was convicted and sentenced to death at Sing Sing for the murder of his client William Marsh Rice.

Miguel Piñero was a playwright, actor and co-founder of the Nuyorican Poets Café. He was a leading member of the Nuyorican literary movement.

Julius Rosenberg and Ethel Rosenberg were American citizens who were convicted of spying on behalf of the Soviet Union. The couple were convicted of providing top-secret information about radar, sonar, jet propulsion engines and valuable nuclear weapon designs. Convicted of espionage in 1951, they were executed by the federal government of the United States in 1953 in the Sing Sing correctional facility in Ossining, New York, becoming the first American civilians to be executed for such charges and the first to suffer that penalty during peacetime.

Ferdinand De Wilton Ward, Jr. (1851–1925), known first as the "Young Napoleon of Finance," and subsequently as "the Best-Hated Man in the United States," was an American swindler. The collapse of his pyramid scheme caused the financial ruin of many people, including famous persons such as Thomas Nast and the former U.S. President Ulysses S. Grant, who had helped him start his banking business.