The Outlaw Who Broke INTO Jail

Most outlaws in the Old West spent their time trying to escape from jail. But in one strange and brazen episode from Arizona Territory, an outlaw named Black Jack Christian did the exact opposite — he broke into a jailhouse.

The High Fives Gang

In the late 1890s, William “Black Jack” Christian led a group of train and bank robbers known as the High Fives Gang. The nickname came from a misunderstood Spanish phrase — supposedly “Jai Fives” — that stuck with the gang. They operated across Arizona, New Mexico, and even into Mexico, leaving a trail of robberies in their wake. Black Jack was known for his fearlessness, quick temper, and willingness to pull a gun at the first sign of trouble.

Trouble in Arizona

In 1896, one of Christian’s gang members was captured after a failed robbery attempt and locked up in the tiny jail of a frontier Arizona town. For most criminals, that would have been the end of the story. But Black Jack wasn’t about to let his partner sit behind bars — especially in a town where lawmen were few and the locals were more accustomed to keeping their heads down than standing up to armed desperados.

Breaking In

In broad daylight, Christian rode into town with a few of his men. Instead of sneaking in under cover of night, they dismounted right in front of the jail, walked through the front door, and demanded the sheriff hand over the prisoner. The stunned lawmen hesitated, but Christian was already pulling his pistol. Facing several armed men, the sheriff had little choice but to hand over the keys. Black Jack unlocked the cell, freed his partner, and — according to some reports — even tipped his hat to the lawmen on the way out.

The Escape

The gang mounted up and rode hard out of town, disappearing into the rugged hills before a posse could be organized. The audacity of the act humiliated local authorities and became the talk of the territory. Newspapers across the West carried the story, sometimes embellishing it into a near-comedic caper, though there was nothing funny about facing down armed outlaws in a cramped jailhouse.

Black Jack’s Fate

Christian’s boldness eventually caught up with him. Later that year, he and his gang were cornered in a canyon by a well-armed posse. A gun battle erupted, and Black Jack was reportedly killed — though his body was never recovered. Some claimed he escaped and lived under an alias; others believed he was buried secretly by his men. The mystery only added to his legend.

Legacy of a Brazen Act

Breaking into jail is almost unheard of in the annals of the Old West. Black Jack Christian’s stunt was a combination of loyalty, arrogance, and sheer bravado. It was the kind of act that cemented his reputation as one of the boldest outlaws of his time — a man willing to walk straight into the lion’s den to free a friend, and walk right back out again.

To learn more about outlaws in the Old West, check out the HOKC video linked below!