Soldiers of Fortune: The 5 Wildest Mercenaries in American History

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Lt. Col. Robert C. MacKenzie, back row, third from right, with some of the Sierra Leone Commando Unit he was training with the Gurkha security guards. MacKenzie was a legendary American mercenary who didn’t quite make our list. Wikimedia Commons photo.

Private armies can be traced as far back in history as the Punic Wars that began in 264 BC, when the Carthaginian empire relied on mercenaries to take on the Roman legions.

Since the inception of the United States in 1776, Americans have continued the grand tradition of waging unauthorized warfare with private armies. From an American pirate who went on to declare himself president of Nicaragua to an adventurer who hired a private army to help establish himself as the king of Afghanistan, here are five of the wildest mercenaries in American history.

William Walker

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William Walker attempted to become president by force rather than through elections. Composite by Coffee or Die Magazine.

William Walker is arguably the most famous and successful mercenary in American history. In the 1800s, groups of American citizens conducted a series of unauthorized military invasions across North America, believing that the United States was destined to expand.

Amid the brazen land grabs, Walker set his sights on conquering Mexico. In 1853, Walker led an army of mercenaries down Mexico’s Baja Peninsula to invade the city of La Paz. When they successfully captured the region, Walker declared himself president and renamed the newly independent nation the Republic of Sonora.

Remarkably, this wasn’t the only time Walker declared himself the supreme leader of a nation. Two years later, Walker led a group of more than 50 mercenaries into Nicaragua to join liberal revolutionaries amid a bloody civil war. When they emerged victorious, he named himself the “presidente” of Nicaragua. His actions angered several surrounding nations, including the United States. Walker was forced to surrender to the US Navy just two years later. American newspapers at the time considered Walker a hero; however, not everyone shared this belief.

In 1859, Walker was approached by British colonists belonging to the island of Roatan in Honduras who requested his help establishing a democratic government. When Walker arrived to hear their proposal, he was met by British Royal Marines and arrested. Walker was turned over to Honduran authorities who killed him via firing squad in 1860. In 1987, Walker — an action-packed biopic starring Ed Harris as the infamous mercenary — hit theaters, quickly becoming a cult classic.

Josiah Harlan

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Josiah Harlan was reportedly the first American to set foot in Afghanistan. Composite by Coffee or Die Magazine.

The first American in Afghanistan wasn’t a diplomat or a US Army soldier but a peculiar man named Josiah Harlan, whom the State Department referred to as “an adventurer from Pennsylvania.” He was 23 when he sailed to Asia to become a surgeon for the East India Company, despite lacking any real medical training. He was so successful at manipulating others that, when he met exiled Shah Shujah al-Moolk (sometimes spelled al-Mulk) and informed him of an elaborate plan to lead a rebellion and reestablish al-Moolk as Afghanistan’s leader, the former Afghan king didn’t bat an eye.

Harlan said he would organize a rebellion against Dost Mohammed Khan — Afghanistan’s sitting king — in exchange for being named chief adviser to al-Moolk. In 1827, Harland’s plan went into motion as he led a motley crew of roughly 100 Muslims, Hindus, and Akali Sikhs through the Indian border town of Ludhiana into Afghanistan. However, Harlan’s planned rebellion was unsuccessful. For the next decade, Harlan became embroiled in the region’s bloody politics. At one point, he received a request to improve the military prowess of the Hazara tribe, a native population of the Hazarajat region in central Afghanistan. When the Hazara prince pledged his loyalty to Harlan in return, Harlan essentially became royalty himself.

In the late 1830s, while surrounded by his personal mercenary army on camels and elephants in the Hindu Kush mountains, Harlan conducted an American flag-raising ceremony to a chorus of a 26-gun salute. He declared himself the Prince of Ghor, the title he received from the Hazara, and the heir of Alexander the Great.

However, he only remained in Afghanistan a short while longer. After witnessing the ill-treatment of Afghan citizens at the hands of British soldiers during the First Anglo-Afghan War, Harlan decided to return home. The international man of mystery later formed Harlan’s Light Cavalry to fight for the Union in the American Civil War, but a mutiny erupted before they could deploy and ended in Harlan being court-martialed for his abrasive leadership. The disgraced military officer lived until 1871, when he died of tuberculosis in San Francisco.

Ira Allen

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Ira Allen helped found the state of Vermont and later became embroiled in mercenary endeavors. Wikimedia Commons images. Composite by Coffee or Die Magazine.

Ira Allen — the respected militia leader of the so-called Green Mountain Boys, aptly named for the forested mountain range in Vermont from which they hailed — fought in several significant battles of the American Revolution.

Allen, alongside his older brother Ethan Allen and his privatized volunteers, joined Benedict Arnold in capturing Fort Ticonderoga near the border of Vermont and New York. The Allen brothers were also present during the invasion of Canada. Ira Allen, an early vocal supporter of Vermont’s independence from the original 13 colonies, became one of the founders of the state in 1790.

In 1795, Allen became entangled in a bizarre conspiracy to purchase arms from Europe to supply Irish rebels in the Canadian rebellion with weapons. Allen purchased 25,000 muskets and 24 cannons from France in exchange for 45,000 acres of land in Vermont. He then sailed from France back to the United States but was intercepted by the British and arrested. Allen was taken to England and prosecuted for his crimes. He was sent to a French prison but was released in 1801 before returning home to Vermont. Although a free man once more, Allen lost his nearly $1 million estate to bankruptcy. He fought litigation and lawsuits against him but ultimately died penniless in 1814.

Sam Dreben

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A newspaper clipping from 1927 reporting the legendary exploits of “Sam Dreben: The Fighting Jew.” Screenshot courtesy of newspapers.com.

Sam Dreben was born to Jewish parents in Russia in 1878. At the age of 20, he left his home for the United States, where he joined the US Army. Dreben’s first taste of combat came in 1899 while serving with the 14th Infantry Regiment during the Moro Rebellion in the southern Philippines.

In 1904, Dreben trained at Fort Bliss in El Paso, Texas, and learned how to handle machine guns — an invaluable skill set he would take with him to future battlefields. After six years of service with the US Army, Dreben’s life as a mercenary began. He was recruited to fight alongside revolutionaries in Guatemala, Honduras, Nicaragua, and Mexico.

In 1913, Dreben became Mexican revolutionary Pancho Villa’s main supplier of weapons, running guns across the Rio Grande over the border. Three years later, Villa conducted his infamous raid in Columbus, New Mexico, that killed 17 Americans and wounded several more in an unprovoked attack. President Woodrow Wilson ordered Gen. John J. Pershing to lead the so-called punitive expedition against Villa. The action caused Dreben to switch sides and vow never to work with Villa again.

Dreben served as Pershing’s personal chauffeur and offered his talents in the field as a scout and spy. In the early spring of 1917, Dreben left his soldier-of-fortune life behind to start a family, but it wasn’t long before his country needed him again when the US became involved in World War I.

Dreben reenlisted and went to Europe with the US Army. He received the Distinguished Service Cross for actions in early October 1918 in Saint-Etienne, France. According to his citation, Dreben discovered a group of German soldiers supporting a machine-gun nest. He rounded up some 30 volunteers and charged the enemy position, capturing four machine guns, killing 40, and taking two prisoners of war. The Americans returned to friendly lines without any casualties.

Dreben arrived back in Texas in 1919, and he settled down to start an insurance business. Unfortunately, Dreben died in 1925 at the age of 46 when a nurse mistakenly injected him with a toxic substance. When newspapers learned of his death, they wrote glowing praise of his professional and renegade life, calling him “The Fighting Jew.” Pershing went so far as to call him “the finest soldier and one of the bravest men I ever know,” sealing Dreben’s status as a legend.

George Washington Bacon III

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George Washington Bacon III was an experienced CIA operations officer who was later killed in Angola in 1976. Photo courtesy of Reddit.

The life of George Washington Bacon III remains mysterious. Bacon served with Army Special Forces during the Vietnam War, conducting recon missions with MACV-SOG into Cambodia and paramilitary operations with the CIA in Laos, where he earned the Intelligence Star, the CIA’s second-highest award.

When the US pulled out of Vietnam, Bacon was disgruntled that his government had betrayed its allies. It remains unclear whether Bacon left the CIA at all, but in late 1975, Bacon offered his services as a mercenary to revolutionary groups fighting against the communists in Angola. Despite his expertise, the seasoned operator was turned away. The same thing happened in Zambia, possibly because the rebels believed he still had connections to the CIA.

In February 1976, Bacon finally managed to join the National Liberation Front of Angola, working with small teams of British mercenaries. The exact circumstances surrounding Bacon’s fate remain unknown, but according to Gary Martin Acker — one of the mercenaries on Bacon’s team — Bacon was shot in the chest and abdomen during an ambush and died on Feb. 14, 1976.

Read Next: That Time US Forces Tore Hundreds of Russian Wagner Group Mercenaries to Pieces in Syria

Matt Fratus is a history staff writer for Coffee or Die. He prides himself on uncovering the most fascinating tales of history by sharing them through any means of engaging storytelling. He writes for his micro-blog @LateNightHistory on Instagram, where he shares the story behind the image. He is also the host of the Late Night History podcast. When not writing about history, Matt enjoys volunteering for One More Wave and rooting for Boston sports teams.
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