Leroy Shear was born Lorenzo C. Stewart in 1838 in upstate New York. He enlisted to fight for the Union in the Civil War, and he was a private in the 14th regiment of the New York Artillery in 1863. By this point in his life, Shear had already been married (and he quickly deserted his wife). Working in the ordinance department of the artillery unit, Stewart was highly regarded – so highly regarded another regiment offered him a chance for a promotion. One problem: Shear would have to desert the 14th to take the higher position.
In October of 1863 that’s exactly what he did – except he got caught. He was placed under arrest and imprisoned in Elmira, awaiting trial. But he was secretly scheming. On October 30, he feigned illness and convinced his guards to take him to two pharmacies in town where he asked the druggists a lot of questions about morphine, which he purchased.
The following evening, the 31st, he visited the guards in the cook-house and offered his guards some whiskey – which he had adulterated with the morphine. His plan was simple: the guards would fall asleep under the influence of the drug and he would escape. But his plan misfired. Several guards did pass out. Two died and the others got very sick. But Stewart didn’t get away. Instead, he was arrested – still in possession of some of the morphine. This time he was tried for murder and was ordered to be shot.
President Lincoln received a petition for clemency from Stewart’s friends who asked for leniency because of Stewart’s youth, the inducement to desert and because he didn’t intend to kill anyone. Further, they raised the issue of his sanity. Stewart had suffered a severe head injury in a fall at age 5, which his mother believed changed his personality. At 15 he suffered what appeared to be sunstroke. He had a history of severe headaches accompanied by drowsiness, nosebleeds and bouts of delirium.
Lincoln ordered the execution stayed and asked John P. Gray, superintendent of the lunatic asylum in Utica, to assess Stewart’s competence. Gray’s report, following an investigation in April of 1864, was mixed. Stewart did suffer from delusions, after which he had no memory of his actions. But he was not insane, Gray concluded.
Gray found Stewart to be erratic and peculiar with a short attention span. He had a history of writing absurd and false letters, often under false names. At the same time, Gray noted Stewart was intelligent, successful in business, and was an avid reader and a quick study. However, he found him lacking in character.
“From the earliest period of this development of his character, even before he was six years of age, he exhibited great moral defects. These have appeared principally in his disregard of the rights of property, and in his untruthfulness. He has always shown himself utterly unworthy of confidence, in every relation of life, and in every position in which he has been placed,” Gray wrote.
Aside from instances where he pulled the hair of fellow prisoners and threw water at them, Gray found little to support the notion that Stewart was insane. Rather, he concluded, Stewart was eccentric.
President Lincoln, after reviewing the matter, would commute Stewart’s sentence from death to ten years at hard labor. By the time of the commutation, however, Stewart had managed to escape. This time, he disappeared for good. First he travelled to Europe and then back to Vermont where he found a position at a bank and lived as a respected member of the community.
By the 1870s, Stewart had become Leroy Channing Shear. He was a delegate to the Republican National Convention and his name was placed before President Rutherford Hayes for a federal position. And it was for this reason he travelled to Washington to meet the president.
Far from receiving the presidential pardon he sought, when Hayes learned of Shear’s past he rescinded any offers of government service and sent him back to Vermont.
It wasn’t long before news of Shear’s past reached his hometown. He was fired at the bank and forced to leave. From there, Shear’s life took a definite downturn. He obtained a job at a building and loan company in Syracuse, but ran off with money he embezzled. In 1884, he was arrested in Burlington, Vermont. The charge: he had written fraudulent checks in New York City.
Shear pleaded guilty and was sentenced to five years in prison. Over the next 25 years, Shear would spend as much or more time in prison than out. A master forger, he adopted Charles R. Clark, William M. Davis and Frank Mallory as his alter egos. His habit of fanciful exaggeration and signing false names, learned as a child, now became his stock in trade.
Shear would visit a city, buy some goods or pay a hotel bill with a check and request some additional funds. Typically Shear would write a $100 check to cover a bill for $40 or so, and depart with his purchases and extra cash. It would be weeks before his fraud was discovered.
The American Bankers Association became so frustrated with Shear that they hired the Pinkerton Detective Agency to track him down. In 1902, the agency succeeded. After circulating his photograph around the country, one of their operatives spotted him and followed him to his residence. After he was identified by one of his victims, Shear was sentenced to four years in Sing Sing prison in New York where he became a teacher in the prison classrooms.