As you may have guessed from his name, Henry Starr is a relative of Belle Starr, the Outlaw Queen. A nephew, to be exact. Henry was born in 1873 in Oklahoma Territory to George Starr, who was half Cherokee, and Mary Scott Starr, who was one quarter Cherokee. Mary came from an educated, law abiding family. George, not so much. Interestingly, Henry was no fan of Belle, whom he found crude and offensive. He told people they were related only by marriage. He didn’t seem to have a problem with his outlaw uncle Sam Starr, or grandfather Tom Starr.
After his father died, his mother married an abusive man, and Henry left home at the age of thirteen. He worked as a cowboy in rough and rowdy northeast Oklahoma, and despite having only a sixth grade education, was something of an intellectual. His first brush with the law was when he borrowed a wagon that was found to have whiskey in it. He pled guilty to having illegal spirits, but insisted he hadn’t known about the whiskey. His next encounter was law enforcement was when he was falsely accused of stealing a horse. After being bailed out of jail by his cousin, he took to the road, jumping bail. It seems that he decided that if he was going to be accused of crimes, he may as well commit them. He and two other men began robbing stores and train stations shortly thereafter.
Two lawmen managed to hunt down Henry in 1892 on a ranch where Henry was rumored to work. A
gunfight ensued and Henry killed a Deputy Marshal and then escaped. Now wanted for murder, Henry and his partners began robbing banks instead of stores. While traveling to California by train, they stopped in Colorado Springs, where law enforcement were finally able to arrest Henry for murder and highway robbery. He was convicted of murder and sentenced to hang in 1893. His lawyers managed to appeal and the US Supreme Court overturned the decision, giving Henry a second trial. He was once again found guilty and sentenced to hang. His lawyers again appealed and Henry got a third trial, in which he pleaded guilty to manslaughter and was sentenced to 15 years.
During his stay in jail, a fellow inmate, Cherokee Bill, attempted a jailbreak with a smuggled gun. A guard was killed in the gunfight that followed. The guards could not disarm Cherokee Bill, so Henry, a friend of Bill, told the guards that he would talk the man into giving up the gun if the guards promised not to kill Bill. The guards agreed and Henry talked Cherokee Bill into giving up his gun. Because of this act, the Cherokee Tribal Government applied for a pardon, and Teddy Roosevelt, who was impressed with Henry’s bravery, reduced the sentence. Henry was released in 1903. After returning to civilian life and working in his mother’s restaurant, he married and had a son, Teddy Roosevelt Starr.
Unfortunately, law enforcement agents from Arkansas still had a bone to pick with Henry regarding a robbery there and demanded extradition in 1904. At that point, Henry went back on the run, formed a new gang and once again began robbing banks. He was captured, convicted and sent back to prison. While in prison, he studied law and wrote his autobiography Thrilling Events; Life of Henry Starr. He was paroled by the governor in 1913. Once free, he began robbing banks again, chalking up a total of 15 robberies in 1914-1915. He was captured in 1915 and once again went to prison, where he finally came to the conclusion
that crime didn’t pay (even though it have been quite lucrative to him). He began speaking and writing to young people and encouraging them not to follow a life of crime, but to instead earn their money the old fashioned way. He was paroled in 1919 because of his good acts. He then turned to acting, producing and starring in a silent movie called A Debtor to the Law, which drove home the senselessness of crime. The movie was a success and he received an offer to make a Hollywood movie, but turned it down, once again fearing extradition to Arkansas. So what did he do then?
He returned to a life of crime. In 1921 he attempted a bank robbery in Harrison, Arkansas, but was shot in the commission of the crime and later died of his wound. He bragged to doctors on his deathbed that he had robbed more banks than any man in America. Indeed, he had made off with more than $60,000 during his career as a bank robber.
