Three-Fingered Jack: The Short, Violent Career of Outlaw Jack Dunlap in the Old West

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In the tumultuous twilight of the American Old West, a figure known by many names, most notably Jack Dunlap or Three-Fingered Jack, carved a brief but violent legacy through bank and train robberies across Arizona. Born in Texas in 1872, this elusive outlaw was also recognized as John Dunlap, Jess Dunlop, and John Patterson, constantly shifting identities as he navigated a life outside the law.

Dunlap’s journey into infamy began far from the dusty trails of crime. He spent his mid-to-late teens as a cowboy, a common path for young men in the era, honing skills that would later paradoxically aid his criminal pursuits. However, the lure of illicit gains proved stronger, and by 1893, he had already embarked on a series of bank robberies that led to his first arrest and incarceration. His release in 1895 marked a turning point, as he swiftly gravitated towards more organized crime.

Three-Fingered Jack: The Short, Violent Career of Outlaw Jack Dunlap in the Old West - 1
Three-Fingered Jack: The Short, Violent Career of Outlaw Jack Dunlap in the Old West – Illustration 1

Joining the Notorious High Fives and Alvord-Stiles Gangs

Upon his return to freedom, Jack Dunlap wasted no time in aligning himself with some of the most feared outlaw collectives of the time. His first notable association was with Black Jack Christian’s infamous High Fives Gang. This group terrorized New Mexico and Arizona, engaging in a wide array of criminal activities that included cattle rustling and robbing stores, banks, and stagecoaches. Dunlap quickly adapted to this ruthless lifestyle, proving his mettle in daring raids.

By 1898, Dunlap had transitioned to another formidable outfit: the Alvord-Stiles Gang. Led by the cunning Burton Alvord and the notorious Billy Stiles, this gang specialized in train robberies, a particularly lucrative and dangerous endeavor of the era. Alongside figures like George and Louis Owens, Bravo Juan Yoas, and Bob Brown, Dunlap participated in a series of audacious hold-ups that kept law enforcement on edge across the southwestern territories. These gangs thrived on speed, intimidation, and a deep knowledge of the rugged terrain, allowing them to evade capture for extended periods.

The Audacious Southern Pacific Express Robbery of 1899

One of the most significant strikes involving Three-Fingered Jack and the Alvord-Stiles Gang occurred at midnight on September 9, 1899. The target was a Southern Pacific Express train, laden with valuables. With precision and brute force, the gang managed to detach the car containing the money. They then used dynamite to blast open the safe, an increasingly common and destructive tactic employed by train robbers of the period. Their haul was substantial, exceeding $10,000, a truly considerable sum in those days.

Following the successful robbery, the gang retreated into the vast and unforgiving expanse of the Chiricahua Mountains. This rugged sanctuary provided an ideal hiding place, allowing them to effectively elude a determined posse led by Sheriff Scott White. Among the ranks of the lawmen was the famed tracker George Scarborough, whose presence underscored the seriousness with which authorities pursued these brazen criminals. Despite their best efforts, Dunlap and his associates vanished into the wilderness, their reputations growing with each successful escape.

The Fatal Encounter at Fairbank: Messenger Milton’s Stand

A few short months later, on February 15, 1900, the gang made their fateful move, attempting to rob a Wells Fargo Express car at the Southern Pacific Railroad depot in Fairbank, Arizona. Fairbank was strategically important, serving as the closest rail station to the booming mining town of Tombstone. This time, however, fate had a different plan for the notorious outlaws.

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Three-Fingered Jack: The Short, Violent Career of Outlaw Jack Dunlap in the Old West – Illustration 2

Unbeknownst to them, the train was under the watchful eye of a formidable adversary: Jeff Davis Milton. A former Texas Ranger and a highly respected lawman, Milton was riding as a messenger for Wells Fargo, a role that often put him in direct confrontation with train robbers. The gang, perhaps underestimating the security, approached the mail car as it pulled into the station, posing as drunken cowboys. Their facade quickly dropped as they opened fire on Milton, who was standing in the open doorway of the car.

Milton sustained a severe shot to the arm and fell back inside the car, momentarily out of sight. The bandits, convinced he was dead, rushed towards the open door, eager to secure their prize. It was a grave miscalculation. As Three-Fingered Jack, leading the charge, reached the doorway, Milton, despite his injury, reappeared. Grabbing a powerful Wells Fargo shotgun, he unleashed a full blast directly into Dunlap’s midsection. Bravo Juan, who was close behind, managed to turn just in time, receiving a less severe but still painful shot to his backside from a greater distance. The intense and unexpected resistance from Milton shattered the gang’s confidence, and they fled in disarray, abandoning their attempt to open the safe.

Dunlap’s Demise and Confession in Tombstone

Dunlap’s wound was catastrophic. He managed to ride only a few miles before succumbing to the pain and blood loss, falling from his horse. The remaining gang members, desperate to escape, abandoned their dying comrade, planning to reconvene outside Contention City. They left Jack Dunlap to his agonizing fate on the desolate trail.

A posse, quickly organized in Fairbank, tracked the bandits and, after 14 grueling hours, discovered Dunlap gravely wounded. They transported him to Tombstone, a town synonymous with frontier justice. Recognizing his imminent death, Dunlap began to talk. His confession provided invaluable information that led directly to the arrest of other gang members, including the leader, Burt Alvord. He even granted an interview to the local newspaper, The Tombstone Prospector, offering a rare glimpse into the mind of a dying outlaw. Jack Dunlap finally succumbed to his wounds on February 24, 1900, his short life of crime brought to an end by the tenacious lawman, Jeff Davis Milton.

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Three-Fingered Jack: The Short, Violent Career of Outlaw Jack Dunlap in the Old West – Illustration 3

Today, Dunlap’s final resting place is in Tombstone’s historic Boot Hill cemetery, a somber testament to the violent lives and sudden deaths that characterized the Old West. He lies in Row 7, Lot 5, near other infamous figures of the era, including Tom McLaury, Frank McLaury, and Billy Clanton. His epitaph, as recorded by The Tombstone Prospector, starkly reads: “Bandit Dies From the Effect of His Wounds. Yesterday morning, about 7 o’clock, Jesse Dunlap, known as Three-Fingered Jack, died at the hospital from the wounds he received while in the holdup at Fairbank last week from the gun in the hands of Messenger Milton.”

Conclusion: A Legacy Etched in Frontier History

The story of Jack Dunlap, alias Three-Fingered Jack, epitomizes the dangerous and often fleeting existence of outlaws in the American Old West. From his beginnings as a cowboy to his involvement with some of the period’s most notorious gangs, Dunlap’s career was marked by daring robberies and desperate escapes. His final, fatal encounter with Jeff Davis Milton at Fairbank serves as a poignant reminder of the relentless pursuit of justice and the high stakes involved in challenging the law on the frontier. Though his life was brief and consumed by crime, Jack Dunlap’s story remains a captivating chapter in the rugged history of Arizona and the untamed Old West.

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