Chuck: And maybe a few generations from now, they'll tell stories about you, - like they do Jesse James… or Billy the Kid. Oh, the myth is so fuckin' romantic…
Jesse Woodson James (September 5, 1847 – April 3, 1882) was an American outlaw, bank and train robber, guerrilla, and leader of the James–Younger Gang. Raised in the "Little Dixie" area of western Missouri, James and his family maintained strong Southern sympathies. He and his brother Frank James joined pro-Confederate guerrillas known as "bushwhackers" operating in Missouri and Kansas during the American Civil War. As followers of William Quantrill and "Bloody Bill" Anderson, they were accused of participating in atrocities against Union soldiers and civilian abolitionists, including the Centralia Massacre in 1864.
After the war, as members of various gangs of outlaws, Jesse and Frank robbed banks, stagecoaches, and trains across the Midwest, gaining national fame and often popular sympathy despite the brutality of their crimes. The James brothers were most active as members of their own gang from about 1866 until 1876, when as a result of their attempted robbery of a bank in Northfield, Minnesota, several members of the gang were captured or killed. They continued in crime for several years afterward, recruiting new members, but came under increasing pressure from law enforcement seeking to bring them to justice. On April 3, 1882, Jesse James was shot and killed by Robert Ford, a new recruit to the gang who hoped to collect a reward on James' head and a promised amnesty for his previous crimes. Already a celebrity in life, James became a legendary figure of the Wild West after his death.
Despite popular portrayals of James as an embodiment of Robin Hood, robbing from the rich and giving to the poor, there is no evidence that he and his gang shared any loot from their robberies with anyone outside their close kinship network. Scholars and historians have characterized James as one of many criminals inspired by the regional insurgencies of ex-Confederates following the Civil War, rather than as a manifestation of alleged economic justice or of frontier lawlessness. James continues to be one of the most iconic figures from the era, and his life has been dramatized and memorialized numerous times.
Billy the Kid (born Henry McCarty September 17 or November 23, 1859 – July 14, 1881, also known as William H. Bonney) was an American Old West outlaw and gunfighter who killed eight men before he was shot and killed at age 21. He took part in New Mexico's Lincoln County War, during which he allegedly committed three murders.
McCarty was orphaned at age 14. The owner of a boarding house gave him a room in exchange for work. His first arrest was for stealing food at age 16 in late 1875. Ten days later, he robbed a Chinese laundry and was arrested, but he escaped only two days later. He tried to stay with his stepfather, and then fled from New Mexico Territory into neighboring Arizona Territory, making him both an outlaw and a federal fugitive. In 1877, McCarty began to refer to himself as "William H. Bonney”.
After murdering a blacksmith during an altercation in August 1877, Bonney became a wanted man in Arizona Territory and returned to New Mexico, where he joined a group of cattle rustlers. He became a well-known figure in the region when he joined the Regulators and took part in the Lincoln County War. In April 1878, the Regulators killed three men, including Lincoln County Sheriff William J. Brady and one of his deputies. Bonney and two other Regulators were later charged with killing all three men.
Bonney's notoriety grew in December 1880 when the Las Vegas Gazette in Las Vegas, New Mexico, and The Sun in New York City carried stories about his crimes. Sheriff Pat Garrett captured Bonney later that month. In April 1881, Bonney was tried and convicted of the murder of Brady, and was sentenced to hang in May of that year. He escaped from jail on April 28, 1881, killing two sheriff's deputies in the process and evading capture for more than two months. Garrett shot and killed Bonney—aged 21—in Fort Sumner on July 14, 1881. During the following decades, legends that Bonney had survived that night grew, and a number of men claimed to be him.