Badass of the Month – Cherokee Bill

As we’ve covered in this particular column, sometimes we “celebrate” some not-so-good-guys. Some have been murderous military tyrants (Santa Anna) and some have just been blood-thirsty mad men that seemingly killed for the sake of killing, like this month’s feature, Cherokee Bill.

I want to stop here and say that no, we’re not great supporters of murdering madmen. In fact, the rule of law is quite popular with us. That said, sometimes we can take bad guys and call them “badass” simply because of their sheer determination to commit their evil. In the case of Santa Anna, he was exiled from Mexico something like 12 times, yet kept coming back to wreak havoc. Cherokee Bill was no different, yet just as bad. An unstoppable force of mayhem, Bill did little but kill, kill, and kill some more so he’s certainly not an admirable person, but we’ll simply give him a tip of the cap for picking a path and seeing it to its awful bloody end at the end of the nooseman’s rope.

Cherokee Bill was born in Fort Concho, Texas, on 8 February 1876. Bill’s father was a hardcore Buffalo Soldier, a Sergeant Major in the 10th U.S. Cavalry, and his mother was half-Cherokee, half-white, but apparently being just one-quarter Cherokee (and not named William) was enough for him to get the nickname Cherokee Bill at some point during his adventures. In any event, Cherokee Bill was infinitely better than his given name, Crawford Goldsby, which simply does nothing to capture the insane badassery that ol’ Cherokee was about to cause.

Bill is believed to have killed his first man at the age of 12, when his brother-in-law told him to go feed some hogs (and was being a real jerk about the whole thing) so Bill capped him in the throat. Bill was tried for murder but acquitted because of his age, because even back in the Old West the judicial system was stupid, though the facts around Bill’s first murder are debated amongst folks that study this sort of stuff.

While this whole murder-at-twelve thing is hotly debated among historians with nothing better to do, what we do know for sure is that Cherokee Bill started getting hardcore into criminal evilness in 1894. It started innocuously enough – the 18-year-old Bill was at a county dance with some hot babe he was totally into – but then all of a sudden he came across some complete jerk 35 year-old guy who was a rival of one of Bill’s older brothers. The jerkface started fronting all up on Bill right in front of his lady, so of course Bill had to get this guy handled by cold-cocking him in the face with a right hook and shooting him a couple times in the chest. The dude ended up pulling through his wounds and surviving, but not before Cherokee Bill had fled the scene of the crime, escaped to the Indian Territories, and joined a gang of hardened criminals intent upon turning the entire Indian Territory into a gigantic cesspool of scum and villainy. Ya know, stuff that was right up Cherokee Bill’s alley.

The next year and a half of Cherokee Bill’s life basically reads like a non-stop series of murders, robberies, asskickings, and hostage situations without any trace of remorse, pity, or mercy. Riding with a hardened, ultra-mustachioed gang of badasses with names like Texas Jack, the Verdigris Kid, Skeeter Baldwin, and Chicken Lucas (presumably the “comic relief” of the gang) these lawless desperadoes went on a criminal rampage that left every city in the Territories in the grip of panic and terror and death. In the summer of 1894, Bill robbed the railroad Depot at Nowata (in present-day Oklahoma), killing the depot operator with a mixture of bad language and bullets. He then proceeded to stand patiently on the platform next to a dead body and wait a few minutes for the next train to show up (he was just hard like that). When the train rolled up to the station, Bill threw open the express car’s door and told the conductor he was robbing the joint. The conductor told Bill to go dry-hump a radiator, so Bill shot him through the beard at point-blank range, gunned down the brake man (just for good measure), robbed the train anyways, and then somehow rode the heck outta there before the cops showed up.

For the next couple months, whenever Bill wasn’t stealing horses, robbing stagecoaches and trains, or moonshining his own whiskey (awesome), he was busting a cylinder’s worth of .45s into anybody unlucky enough to be within a few hundred feet of whatever crime he was in the process of committing. Like one time he robbed a bank and somehow ended up shooting the town barber in the back for a reason that probably made sense at the time. Another time he was robbing a different bank, and some local painter peeked in the window to see what was going on, so Bill capped that jerk through the window, said some shit about how he had no appreciation for the fine arts, and went right back to emptying the contents of the bank safe down his pants. (Interestingly, despite all the robbing/pillaging/plundering/murdering this guy did, this murder was the crime he actually ended up hanging for.)

But all things (both good and miserable) need to come to an end sometime, and Cherokee Bill was finally arrested in February of 1895. Bill was at some girl’s house, hungover as hell from a night of whiskey, morphine, and sexing, and when Bill went to light a hand-rolled cigarette in her fireplace some jerkwad deputy ran into the house and clubbed Bill in the back of the head with a giant log of firewood. The deputy later testified that he thought he’d hit Bill hard enough to kill him, but instead Bill just fell down, rolled over, and started throwing haymaker punches at anything that moved. It took three deputies fifteen minutes to finally subdue him, but Bill still wasn’t done resisting arrest – on the way to Nowata for trial he snapped his handcuffs (!) and tried to grab the pistol from one of his guards’ holsters. The assaulted guard ended up falling out of the stagecoach, taking the pistol with him, and two deputies with shotguns managed to convince Bill to put on a fresh set of manacles and settle the hell down.

As you can imagine, Cherokee Bill still wasn’t finished. When the sentence of “death by hanging” was issued by Judge Isaac Parker, Bill’s mom started freaking out all hysterically, but Bill, in the middle of the courtroom, just turned to her, smiled a huge grin, and said cryptically, “Hey, I ain’t dead yet.”

A few days later an astute janitor found a six-shooter hidden in a bucket of lye in the prison bathroom.

Three days after that, when a prison guard went to check on the prisoners, Bill pulled a false brick out of the wall of his cell, revealing a hand-dug hole behind the wall that had a revolver stashed in it. Bill drew the gun, killed the guard, and then orchestrated a fifteen-minute prison standoff, holding the guards off from his prison cell, shooting at anyone who peeked their heads around the corner. The terrified guards later testified that he was taunting them mercilessly, laughing like a madman, and, according to some versions, gobbling like a turkey every time he fired. This is weird, but I think it’s weird in a good way.

The situation was eventually diffused by a fellow inmate, Bill was convicted for a second murder, and on 17 March 1896 Cherokee Bill was executed at a well-attended public hanging. On his way out to the gallows, all he said to the crowd was, “This is about as good a day to die as any”. He was twenty years old.


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