Rogues of the American Revolution, from the Doan Gang to Ben Franklin’s Son

Rogues of the American Revolution included spies, outlaws, guerrilla fighters, and even Benjamin Franklin’s own son!

The American Revolution was far from the “gentleman’s war” that some movies and TV shows may suggest.

In reality, it was a brutal, neighbor-against-neighbor conflict that relied on guerrilla actions and unorthodox tactics carried out by both sides.

That was in stark contrast to the conflicts in Europe fought throughout the 18th century, which were highly formalized and noted for the professionalized conduct that aimed for strategic, rather than existential, victories.

The wars in Europe featured seasonal campaigning, fought by professional, drilled standing armies, with codes of conduct observed by officers on both sides.

The American colonists didn’t exactly play by British rules of war, but it should be noted that their tactics won the day (with some help from the French).

More importantly, the British didn’t stick to their strict codes of honor either. As the war went on, the British employed many of the same tactics as the American colonists.

There were also the many “rogues” of the American Revolution, who employed truly unorthodox methods to keep the colonies under the control of King George III!

CHECK OUT the entire Hook & Barrel American Revolution Series

The Doan Gang: America’s First Outlaws

Among the most violent groups of rogues fighting for the British cause were the Doan Gang, a group of Pennsylvania Quaker brothers and cousins. The core group consisted of five men, but more than 60 men and women supported the gang.

In many ways, they could be compared to the fictionalized “Peaky Blinders,” as they were a notorious and tight-knit criminal organization that engaged in robbery, extortion and intimidation. They also acted as British spies and saboteurs.

If ever a group defined the term rogue of the American Revolution, the Doan Gang is it.

Instead of donning stylish suits, the Doan Gang was composed of outdoorsmen and skilled horsemen who hid in caves and operated in the rural, wooded environment of Bucks County, Pennsylvania. Loyalists compared them to Robin Hood, whereas Patriots called them demons!

The Doan Gang assisted the British Army by providing intelligence in advance of the Battle of Long Island, and later robbed Continental tax collectors.

Often described as America’s first outlaws, the key members met the same ends as other criminals to come. One brother was shot dead in 1783, and two others were hanged after the American Revolution for “outlawry.”

William Franklin Chose the Crown Over His Father’s Cause

The recognized but still illegitimate son of famed Founding Father Benjamin Franklin, William Franklin served as royal governor of New Jersey.

In early 1775, he told the colony lawmakers, “You have now pointed out to you, gentlemen, two roads, one evidently leading to peace, happiness, and a restoration of the public tranquility. The other inevitably conducting you to anarchy, misery, and all the horrors of a civil war.”

William Franklin served with provincial troops in King George’s War (1744-48), reaching the rank of captain.

Although his father urged him to join the Continental Army, where his prior military service would earn him a high-ranking position, William was a devoted Loyalist.

That led to his removal as royal governor by the Continental Congress and imprisonment.

After being released in a prisoner exchange, he relocated to New York City, where he became the chief leader of American Loyalists throughout the colonies, and he is credited with creating an unofficial spy network within the Loyalist community.

Franklin later organized the Associated Loyalists to engage in guerrilla tactics against Continental Army forces in New York, New Jersey and Connecticut.

After the British defeat at the Battle of Yorktown in October 1781, the younger Franklin traveled to London, believing that the British would still come out triumphant.

He gained support for the cause until the Treaty of Paris, brokered by Franklin’s father, was concluded, ending the conflict and recognizing an independent United States of America. The men never reconciled.

READ MORE: How Hunters Kept the Continental Army Fed

John Bacon and the Pine Robbers Spread Fear in New Jersey

William Franklin was more of a politician than a fighter, but he's still an important rogue of the American Revolution.

He worked with and directed men like John Bacon, the leader of the Pine Robbers, a band of Loyalist guerrilla fighters who hid out in the Pine Barrens of south-central New Jersey (the location of the third-season episode of The Sopranos).

The group preyed on the Patriots in the final years of the Revolutionary War. It was even responsible for the October 1782 Long Beach Island Massacre, a year after the Battle of Yorktown, when hostilities had been largely put on hold.

Two months later, on Dec. 27, 1782, Bacon and his Loyalist militia fought a unit of Continental militia, commanded by Richard Shreve and Edward Thomas, at one of the lesser-known battles, the Battle of Cedar Bridge in Barnegat Township, New Jersey.

It is recognized as one of the last skirmishes of the Revolutionary War fought on American soil. Bacon, who was wounded in the fighting, escaped, but he was hunted down and killed on March 31, 1783.

John André and Benedict Arnold Are the Most Famous Rogues of the American Revolution

The two most infamous rogues of the American Revolution will forever be closely linked: the spy Major John André, and the traitor General Benedict Arnold.

André served as the head of the British Army’s intelligence operations and, by most accounts, was an honorable, charismatic, and even gallant officer.

Unlike the Doan gang or John Bacon, André was truly an officer and a gentleman. His captors, including George Washington, admired his character. He was certainly the most charming rogue of the American Revolution.

On Sept. 23, 1780, near Tarrytown, New York, Major André was caught following a meeting with Arnold, who had offered to turn over control of the American fort at West Point.

Convicted of espionage, André was ordered to be executed by hanging. Although he requested to die by firing squad as a soldier instead of being hanged as a spy, the request was denied.

His execution led to an outburst of anti-American sentiment in Great Britain, and several prominent leaders of the Patriot cause, notably the Marquis de Lafayette, publicly disagreed with the decision.

One reason that André’s fate may have been sealed was that General Arnold had escaped to the British lines.

Today, Benedict Arnold’s name is practically synonymous with “traitor,” and he remains the highest-ranking turncoat in American history.

The irony is that had he fought with distinction for the American Continental Army, he would have risen to the rank of major general. Washington had given him his fullest trust and placed him in command of West Point.

Benedict Arnold Chased Honor and Found Infamy

Historians have suggested that Arnold was a narcissist, self-serving, greedy, and intensely vain. His bravery in battle was the result of reckless courage, fueled by a need for admiration and a deep-seated belief in his own superiority.

Hypersensitive to slights, obsessed with his legacy and personal glory, Arnold was known to be short-tempered. Arnold also believed he was undervalued by the Continental Congress, which led him to believe his betrayal was justified.

After changing sides, he was commissioned as a brigadier general in the British Army and placed in command of the American Legion, made up of Loyalist supporters.

As a traitor, even one who had a distinguished career as a front-line officer, Arnold was never respected or trusted by the British.

General Charles Cornwallis disregarded Arnold’s advice to locate a permanent base away from the coast, which historians have suggested may have averted his defeat at the Battle of Yorktown.

Benjamin Franklin wrote of Arnold, “Judas sold only one man, Arnold three million.”