5 Habits of Highly Effective Outlaws

By David Norris

Guns? Check. Masks? Check. Poetry book? If you're going to rob a stagecoach, here's how to do it with flair. 

1. IF YOU'RE A POET, SHOW IT.

Even if you’re a no-good, law-flouting bandit, it pays to mind your manners—and your meter. In California, between 1875 and 1883, Charles E. “Black Bart” Boles held up more than two dozen Wells Fargo stagecoaches. Even though he seemed to have an intense private grudge against the bank, he was always polite to its employees, asking stage drivers to “please” throw down the money. Stranger still, Boles often left poetry at his crime scenes. This poem was his most well-known:

I’ve labored long and hard for bread, For honor and for riches, But on my corns too long you’ve tread, You fine-haired sons of bitches.

In 1883, Boles was wounded during a holdup and accidentally left a handkerchief at the crime scene. When Wells Fargo detectives traced it back to him, he was arrested and imprisoned, and although Boles’s career as a robber was over, his literary influence was just beginning. During his imprisonment, several copycat stagecoach robbers left truly dreadful bits of poetry at the scenes of their crimes.

2. SPIN THE MEDIA.

Jesse James spent as much time honing his public image as he did robbing people. In fact, James frequently wrote letters to newspapers, stressing that his gang never attacked innocent farmers, only corrupt banks and railroad companies. He also claimed lawmen hounded James and his brothers because they had been Confederate soldiers, which won the gang sympathy in the South. His letters were widely reprinted, even in The New York Times, helping turn the Missouri bandits into national legends.

One night in 1875, Pinkerton detectives threw a flare into the James family home. The agents were trying to light up the dark house so they could shoot at the outlaws, but the flare exploded in the fireplace, killing Jesse’s young half-brother and maiming his mother, who lost her right forearm. James made the incident seem even worse than it was in his letters to the press, falsely claiming the detectives had tossed a 32-pound military shell into his mother’s home. The public was horrified, and after the explosion, Pinkerton agents received little help from Jesse’s neighbors, who were often happy to provide the James gang with food, information, and hiding places.

3. ROB SMARTER, NOT HARDER.

In the early 1900s, automobiles were starting to replace stagecoaches, which meant that stagecoach robbers were a dying breed. One of the last havens for the bandits was Yellowstone National Park, because the park didn’t allow motor vehicles. On the lonely, isolated trails, robbers could loot stagecoaches with remarkable efficiency. On July 29, 1914, an ex-con named Ed Trafton chose a spot about eight miles from the Old Faithful geyser, where there was only one route for stagecoaches. With the aid of an armed accomplice who kept his victims from turning around to get help, Trafton held up 15 coaches, one by one, as though he were operating a drive-through bank.

4. GET IN TOUCH WITH YOUR FEMININE SIDE.

During the 17th century, English highwayman Tom Rowland menaced coach travelers with a string of holdups that lasted for 18 years, and the entire time, he was dressed like a lady. Rowland worked hard to keep up the charade, even riding sidesaddle when getting away from crime scenes. Caught and convicted in 1699, Rowland was hanged at Tyburn Hill, the historic place of execution for London-area criminals.

5. WAIT FOR THE OTHER SHOE TO DROP.

Arizona stagecoach robber Bill Brazelton threw lawmen off his trail with a cunning horseshoe trick. Before committing a crime, he would place shoes on his horse normally, then once he’d stolen the goods, he’d quickly turn the shoes around. After he rode off, it would look as though there were two sets of tracks leading to the crime scene, but no tracks leading away.

Brazelton’s scheme worked until one day in 1878, when one horseshoe fell off his steed after a robbery. The horse left behind a bizarre set of tracks, with three shod hooves running in one direction and one bare hoof running in the other. A suspicious tracker traced the odd hoofprints to a corral near Tucson, where a posse laid an ambush for Brazelton, and he was killed in the attack. That thing about horseshoes being lucky? Not so much.

This article originally appeared in mental_floss magazine. Get a risk-free issue!