Harry Head: Unraveling the Enigmatic Arizona Outlaw’s Violent Legacy

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In the tumultuous landscape of the Old West, where justice was often swift and violent, figures like Harry Head emerged, leaving a trail of daring robberies and deadly confrontations. Known also as Harry the Kid, Harry Head was a notorious cattle rustler and stagecoach bandit whose brief but brutal career intertwined with some of Arizona’s most infamous outlaw factions, particularly the notorious Clanton Gang.

The Audacious Contention Stagecoach Robbery

The name Harry Head first gained significant notoriety on March 15, 1881, when he, alongside fellow outlaws Bill Leonard and Jim Crane, executed a bold stagecoach ambush. The location was approximately one mile outside the burgeoning mining town of Contention, Arizona, a strategic point where the stagecoach, laden with valuable cargo and unsuspecting passengers, was forced to navigate a challenging, steep grade. This section of road provided the perfect opportunity for the bandits to strike, as the coach’s pace significantly slowed, making it an easy target.

Harry Head: Unraveling the Enigmatic Arizona Outlaw's Violent Legacy - 1
Harry Head: Unraveling the Enigmatic Arizona Outlaw’s Violent Legacy – Illustration 1

The targeted coach, a vital link in the Wells Fargo network, was carrying a staggering sum: an estimated $26,000 in silver and gold, a fortune that would have cemented the reputations of any successful robbers. Aboard were eight passengers, their journey through the rugged Arizona Territory abruptly interrupted by the chilling reality of an Old West holdup. To mask their identities and prevent future identification, the three outlaws had meticulously donned disguises, wearing elaborate wigs and false beards, a detail that initially complicated the subsequent investigation.

However, this was no ordinary stagecoach. Guarding the valuable shipment and its occupants was lawman Bob Paul, a figure known for his courage and dedication to upholding the law. As the robbers sprang their ambush, gunfire erupted, transforming the quiet Arizona road into a chaotic scene of violence. In the ensuing shootout, stagecoach driver Budd Philpot and one of the passengers tragically lost their lives. Bill Leonard, one of the outlaws, also sustained a wound in the exchange. Amidst the chaos, the horses, startled by the gunfire, bolted, threatening to drag the stage and its remaining occupants into further danger. It was Bob Paul’s quick thinking and bravery that brought the runaway coach under control, while the would-be robbers, their plan partly thwarted and having incurred casualties, fled the scene empty-handed.

The Investigation and Pursuit

The immediate aftermath saw law enforcement, spearheaded by the resolute Bob Paul and the legendary Wyatt Earp, launch a relentless investigation. Their initial suspicions quickly honed in on a local individual named Luther King. King was subsequently arrested by Morgan Earp, one of Wyatt’s brothers, who was deeply involved in the frontier justice system. Under interrogation, King confessed his peripheral involvement, claiming he had merely been present to hold the horses during the ambush. More importantly, his confession implicated his fellow conspirators: Harry Head, Jim Crane, and Bill Leonard. This critical information provided the lawmen with a clear path forward.

However, the pursuit of justice was fraught with setbacks. In a surprising turn of events, Luther King managed to escape from jail, further complicating the efforts to bring the entire gang to account. Meanwhile, Wells Fargo, determined to recover its stolen assets and punish those responsible for the violence, publicly announced a substantial reward of $2,000 for each of the three remaining men — Harry Head, Crane, and Leonard — offering it “dead or alive.” This bounty intensified the hunt, ensuring that the outlaws would find little peace on the frontier.

A Fatal Encounter in Eureka, New Mexico

Several months later, in June of that same year, the trio of outlaws, undeterred by their previous failure and the bounty on their heads, attempted another robbery. This time, their target was a store located in Eureka, New Mexico. Believing they could easily overpower the proprietors, they initiated their holdup. However, store owners Bill and Ike Haslett proved to be far more resilient and formidable than the outlaws had anticipated. The Haslett brothers bravely fought back, transforming what was intended to be a quick robbery into a deadly gunfight.

In the ensuing struggle, both Harry Head and Bill Leonard were killed, their outlaw careers brought to an abrupt and violent end. Jim Crane, however, managed to escape the shootout, narrowly avoiding the same fate as his companions. His escape would prove to have dire consequences, as Crane was consumed by a burning desire for revenge against the Haslett brothers for the deaths of his associates.

The Haslett Brothers’ Last Stand

True to his vengeful nature, Jim Crane wasted no time in orchestrating a brutal reprisal. Later that very month, Crane assembled a formidable posse of fellow outlaws, including notorious figures such as Curly Bill Brocius, Frank Stillwell, Pony Diehl, Pete Spence, and at least five other hardened men. Their sole mission was to hunt down and eliminate the Haslett brothers. This was not merely about robbery; it was a cold, calculated act of frontier justice on the part of the outlaws.

The heavily armed group tracked the Haslett brothers for approximately twenty-six miles from Eureka before finally catching up to them. What followed was a desperate and ultimately tragic struggle. The Hasletts, despite being severely outnumbered, fought with incredible bravery and determination. In a testament to their resilience and skill, they managed to kill two and wound three of Crane’s attacking party, inflicting significant damage on the outlaw gang. However, the sheer numerical superiority of Crane’s contingent eventually overwhelmed the brothers, and they were tragically killed.

The ferocity and details of this bloody encounter were quickly disseminated across the region, making headlines in local newspapers. The Arizona Star, a prominent publication of the era, reported on the gunfight on June 23, 1881, vividly describing the events:

“The killing of Bill Leonard and Harry, the Kid, at Eureka, New Mexico, by the Haslett brothers has been summarily avenged. It appears that a cowboy named Crane organized and led a band of congenial spirits in the work of vengeance. They followed the Haslett boys for some twenty-six miles from Eureka before overtaking them, and as soon as they came up with them, the fight to the death commenced. The Haslett boys were game and made a brave fight, killing two and wounding three of the Crane party, but being overpowered, were finally killed.”

Conclusion: A Minor Figure in a Violent Era

Though not as widely celebrated or reviled as some of his more famous contemporaries, Harry Head remains a significant, albeit secondary, figure in the tapestry of the Old West’s violent frontier. His involvement in the Contention stagecoach robbery brought him into direct conflict with prominent lawmen like Wyatt Earp and Bob Paul, while his demise in Eureka, New Mexico, sparked a bloody revenge plot that underscored the brutal realities of outlaw life. Harry Head’s brief career serves as a vivid reminder of the constant struggle between law and lawlessness that defined the American Southwest during its formative years, a period marked by both immense danger and the relentless pursuit of fortune.

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