Patriot Scoundrel

An Early American Enigma

As I continue to profile characters in or mentioned in my upcoming novel, The North Spy, there is one in a cameo role who seemed to be at the periphery of interesting events–– not always in a good way. And that is an understatement. James Wilkinson is one of those enigmatic characters who managed to place himself where he could do the most good for–– himself! 

James Wilkinson

Various historians and writers use James Wilkinson's own writings, and his account of things, while first-hand, is not unbiased. Wilkinson appears in The Cavalier Spy and The North Spy, and I do not portray him very favorably. He becomes a bit of a foil for my protagonist, Jeremiah Creed, and adds a certain ambiguity to things. This will be part 1 of a 2-part treatment of Wilkinson.

Chesapeake Roots

Maryland was the birthplace of James Wilkinson, whose family were mid-level landholders in Calvert County. He was born to Joseph and Althea Wilkinson in Charles County on 24 March 1757. He spent time on the family estate, Stoakely Man, which his father inherited from his grandfather, but by the time James was seven, debt caused his father to lose the estate, which was auctioned off in lots. A small parcel was retained, but James's older brother Joseph inherited it.

Wilkinson hailed from Maryland's Western Shore

A landless second son often had few prospects, but fortunately, his grandmother had enough money and connection to ensure a decent education: first tutoring in his early years and later the study of medicine at the University of Pennsylvania. This would have given him a boost in his career, but politics and the struggle with Britain got in the way of his path to becoming a surgeon.

Revolutionary Youth

James Wilkinson was just eighteen when the "Shot Heard Round the World" changed everything and put him on a pathway to potential military glory. He began his service in 1775 with Thompson's Rifle Battalion, where he was promoted to captain that September. The battalion, formed from "Associator" companies, marched to Massachusetts and joined the newly formed army assembling around Boston.

Pennsylvania Infantry

New England Triumph

But Wilkinson, who we'll see was quick to spy opportunity, soon got himself seconded to General Nathanael Greene as an aide–– a role he would often play to his advantage. By his account, he helped lay in the batteries on Dorchester Heights, an act that sent the British packing.

Dorchester Heights

New York Debacle

He marched with the Continental Army as it scurried south to defend New York in spring 1776. This time as a company commander in Thompson's battalion, on 1 July 1776, The First Pennsylvania Regiment of the Continental Line would play a role in the brutal fighting on Long Island in August.

Retreat from Long Island

Canada Collapse

The campaign to wrest Canada from the British was going badly. While General Washington and Howe danced their armies around New York and across the Jerseys, another front was raging in hot combat but in a much colder climate. Wilkinson went north with reinforcement for Benedict Arnold, who assumed command when the expedition's commander, General Richard Montgomery, was mortally wounded in the assault of Quebec that December. Wilkinson got himself appointed as an aide to Arnold, but the arrival of a relief army under General John Burgoyne sent the Americans into a retreat back to New York.

Basking Ridge Mystery

Arnold would soon fight the invading British to a standstill, but by then, the now Major Wilkinson had gotten himself reassigned as an aide to General Charles Lee, second in command of the Continental Army, during Lee's controversial (he lagged) march from the Hudson Highlands to join Washington outside Philadelphia in December 1776. On a cold, snowy morning, Wilkinson was with Lee, who had left his division and ridden to Widow White's Tavern in Basking Ridge, when British dragoons attacked him under Banastre Tarleton. Lee was captured, but Wilkinson escaped. His account of this is self-serving to him and denigrates Lee. My account in The Cavalier Spy tries to even things up a bit.

Wilkinson escaped Lee's fate at Widow White's

Saratoga Surrender

By the summer of 1777, Wilkinson was a Lieutenant Colonel and Assistant Adjutant to the new commander of the Northern Department, Major General Horatio Gates. He played an active staff role in the dramatic battles and the British Army's surrender. In my novel, The North Spy, he appears competent but manipulative in his interactions with Horatio Gates, Benedict Arnold, Dan Morgan, and my fictional protagonist, Jeremiah Creed.

General Burgoyne's surrender at Saratoga

Career Summit

Wilkinson burst onto the national scene when Gates selected him to ride to Congress with news of the Saratoga victory–– a direct affront to General George Washington and a precursor to upcoming political machinations such as the "Conway Cabal." Wilkinson tarried in his delivery to settle personal matters and, of course, embellished his role. He did this so well that Congress brevetted the twenty-year-old lieutenant colonel a brigadier general even though he had not commanded more than a company of troops. This promotion, and suspicions of his and Gates's connections to the Conway Cabal, caused many officers to turn against him. In fairness, this was a typical reaction among the Continental Army's higher ranks.

Wilkinson's news to Congress bypassed Washington

Brevet Brigadier

With promotion in November 1777 came a new job–– a seat on the Board of War. Various political intrigues and accusations led to him leaving the prestigious Board, which was charged with overseeing the conduct of the war in the spring of 1778. A year later, Congress found another administrative post for him–– Clothier General of the Army. Clearly, his reputation as a politician, lack of previous command experience, and getting cross with the commander-in-chief precluded a field command. But things did not go well, and he resigned from the position in the spring of 1781.

Wilkinson was an unlikely clothier

 for the Continental Army

Family Affair

Before we wrap up Wilkinson's Continental Army career, we'll examine his personal life. While stationed around Philadelphia, the newly-breveted general married Ann Biddle. The couple wed on 12 November 1778. Anne was from one of the most prominent families in Philadelphia. Her first cousin was Charles Biddle, who served as a merchant mariner (privateer), a light infantry officer, and a naval officer during the war. Biddle later became highly prominent in Pennsylvania politics and was closely connected to Aaron Burr. These connections would play out in Wilkinson's future in surprising ways as our story shifts to the frontier.

Connection to Biddle would have

 second-order effects

The Saint

Not the infamous TV character Simon Templar played by Roger Moore, but a son of County Kildare, a professional British officer, and a key contributor to the Saratoga Campaign. In fact, Lieutenant Colonel Barry St. Leger’s push from the west was the third prong of the triple pincer against Albany in a grand plan to defeat the Americans once and for all. Often seen as an afterthought, St. Leger's role was a vital part of a strategy designed to overwhelm the rebels in New York.

Roger Moore as Simon Templar

Born in the Land of Saints and Scholars

Barrimore Matthew St. Leger was born in May 1737 in County Kildare, Ireland, and was a nephew of the Fourth Viscount Doneraille. This date is actually his baptism date, as Irish tradition was to record baptisms more carefully than births during a time when infant mortality was common. Barry’s father, Sir John St. Leger, was a prominent Irish judge. His brother, Anthony St. Leger, served in Parliament and the military, reaching the rank of major general.

Anthony St. Leger

Saint to Scholar to Soldier

The high-born St. Leger attended the esteemed halls of Eton and Cambridge before joining as an ensign with the 28th Regiment in April 1756. His regiment immediately sailed to North America for the French and Indian War. St. Leger served with some distinction under British General James Abercromby. 

James Abercromby

By 1758, the young Irishman was a captain in the 48th Regiment and participated in General Jeffery Amherst’s Siege of Louisbourg. St. Leger was appointed brigade major (a staff position, not a rank) during General James Murray’s advance on Montreal in 1760, and in September 1762, he was promoted to major in the 95th Regiment. The French and Indian War had been beneficial for the Viscount’s nephew. The Revolutionary War, however, would be a mixed experience. 

Jeffery Amherst

Defending Canada

When resistance erupted into rebellion and war in 1775, St. Leger served as lieutenant colonel of the 34th Regiment. Barry arrived in Canada in the spring of 1776. He and his regiment helped Governor-General Guy Carleton repel the invading American forces throughout the summer and fall of that year. St. Leger and the 34th recaptured Fort Ticonderoga during the southward drive but withdrew when Carleton decided to end the campaign and return north into winter quarters. 

Guy Carleton

A Grand Strategy

The irrepresible General John Burgoyne arrived from England in early 1777 with reinforcements from Lord Germain, the Minister for Colonies. “Gentleman Johnny” also brought his bold plan of a three-pronged attack to capture Albany, New York. His aim was to sever the stubborn New England colonies from the rest of the colonies. What would happen after that was unclear.

Western Approach

A lesser-known but essential part of Burgoyne’s plan was a supporting move along the Mohawk River to draw away rebel forces, punish rebel farmers, and link up with his main force near Albany. Burgoyne chose St. Leger to lead the western branch because of his experience and skill in navigating the northern wilderness. 

John Burgoyne

Brevet Brigadier General

On June 23, 1777, St. Leger’s combined force of about 800 British regulars, Hessians, Loyalists, and Canadians set out from Montreal. They included Loyalists under Colonel John Johnson and Major Walter Butler, along with some British and Hessian troops. St. Leger, who had been breveted a brigadier general for the campaign, prioritized speed over firepower, so he decided to leave behind heavier artillery to avoid slowing the wilderness march. He did bring along a few light guns, but these would prove inadequate for the task.

Barry St. Leger

Drums Along the Mohawk

On 25 July, a flotilla of British ships and barges landed St. Leger’s forces at Oswego, New York. They were quickly joined by 800 Native warriors led by Iroquois War Chief Joseph Brant and Seneca War Chief Cornplanter. 

Chief Joseph Brant

They quickly moved up the Mohawk River valley following Burgoyne’s plan, passing friendly Iroquois villages and undefended farmland. 

Iroquois village on the Mohawk River

But St. Leger soon faced his first obstacle—rebel-controlled Fort Stanwix (present-day Rome, NY), which was fiercely defending the upper valley against his advance. To St. Leger’s dismay—reports from Indian scouts and spies proved accurate. 

Fort Stanwix

The Continental Army’s Northern Department commander, General Philip Schuyler, recently repaired the fortification and garrisoned it with 750 men of the 3rd New York Regiment under Colonel Peter Gansevoort, with Lieutenant Colonel Marinus Willet as his deputy.

Peter Gansevoort

Fort Stanwix Besieged

When St. Leger arrived outside Fort Stanwix, he sprang into action, conducting a “leader’s reconnaissance" of the post. He quickly realized he had underestimated the size and strength of the place. Lacking the heavy guns to pound the fort into submission, St. Leger ordered his Indian allies to encircle it in what was a very soft siege. 

Iroquois Braves surround Fort Stanwix

He then tried to bluff the defenders into surrender by showcasing his entire force. Ironically, the many native warriors convinced the Americans they would be slaughtered if they surrendered. St. Leger’s surrender summons fell flat. Frustrated, he ordered a bombardment of the fort, but his small-caliber guns proved ineffective.

Oriskany Ambush

Farther up the valley to the east, the Tryon County militia gathered when word of the British invasion reached them. A column of 800 men under Colonel Nicholas Herkimer marched out of Fort Dayton, aiming to relieve Stanwix. But Molly Brant, sister of Chief Joseph Brant, warned St. Leger of the new threat. He responded by sending a force of Loyalists and Indians into the dense forest near the village of Oriskany, to the east. 

Molly Brant

On 6 August, beneath a dense canopy of ancient woods, they launched a devastating ambush on the militia, which was halfway across a deep gulley. A fierce firefight broke out. Curtains of gunfire tore through the hardwood and scythed down brush and branches. Men fell on both sides, but with many dead and wounded, including Herkimer, the Tryon County militia retreated behind the cover of thick gun smoke.

Oriskany Ambush & Firefight

Stubborn Resistance

Back at Fort Stanwix, the Americans had a few tricks of their own. With the besiegers reduced to sending forces to Oriskany, Lieutenant Colonel Marinus Willet successfully launched a sortie from the defenses and captured St. Leger’s camp, thoroughly looting it. The loss of supplies discouraged the tribesmen, and they began abandoning St. Leger’s column.

Marinus Willet

Desperate, St. Leger once again threatened the defenders with massacre unless they surrendered. Gansevoort agreed to a truce but was determined to defend the fort. He sent Willett to ride through British lines to Stillwater, report the situation to General Philip Schuyler, and ask for reinforcements. 

Arnold’s Deception

And so, it was. General Benedict Arnold assembled a force to drive the British from Stanwix. But Arnold was as clever as he was brave and bold. He sent a unhinged man named Hon Yost to “desert” the British. His rantings of a relief force “more numerous than the leaves on trees” frightened the remaining warriors, who fled west. 

Benedict Arnold

Seeing his hopeless situation, St. Leger was forced to abandon his siege of Fort Stanwix. On August 25, his regulars, Hessians, Loyalists, and a few loyal Indian allies, traveled west along the Mohawk River and headed for Canada. St. Leger’s failure to reach Albany and support Burgoyne directly helped lead to the surrender at Saratoga in October 1777.

Return to Ticonderoga

St. Leger did not dwell on his failed campaign. Instead, he quickly took action after returning to Montreal, persuading limited forces from Governor Guy Carleton. He led his troops south to directly reinforce Burgoyne. However, they had just reached Fort Ticonderoga when news of the Saratoga surrender arrived in October 1777. 

Fort Ticonderoga

Guerrilla Warrior

For the rest of the war, St. Leger remained in active command and established himself as a specialist in irregular warfare. He led multiple raids against the Americans in upper New York, which became a battleground of brutal partisan and guerrilla fighting throughout the conflict. Spying, betrayal, raids, ambushes, assassinations, and burning would ravage upper and central New York.

Loyalist raiders

St. Leger was involved in a failed attempt to kidnap General Philip Schuyler. In 1781, the new commander in Canada, General Frederick Haldimand, sent him back to Ticonderoga to meet with discontented rebel leader Ethan Allen. However, the plan to separate Vermont from the rebels did not succeed.

Philip Schuyler

Canadian Service

Unlike most of his fellow officers, St. Leger did not return to England or sail to another theater after the 1783 Treaty of Paris. Instead, he stayed in Canada. In 1784, he was promoted to brigadier general and took over as commander from Haldimand. But by 1785, poor health caused by the hardships of campaigning forced him to step down and retire from active service. St. Leger died in Worksop, Nottinghamshire, England, on December 23, 1793. 

Frederick Haldimand

Legacy

St. Leger's legacy is mixed. He was a talented tactical leader capable of planning and organizing complex operations across large wilderness areas. However, his only major independent command ended in failure due to a combination of poor decision-making (remember the heavy guns?), failure to keep his native allies in line, and unforeseen resistance from American forces that were more formidable than expected. 

But unlike his commander Burgoyne, "The Saint" knew when to quit and pulled his troops out of a dangerous situation. Facing the defenders at Fort Stanwix combined with General Benedict Arnold's relief force would have likely led to the destruction of his force. Instead, his troops would live to fight another day and continue to harass and threaten upper New York for the rest of the war, while Burgoyne’s stubborn refusal to consolidate caused his larger army to march off to rebel prisons.

The Old Patroon

The Dutch settlers of New York and East Jersey were among the hardest-working Europeans to settle in North America. Thrifty, ambitious, and organized, they expanded their foothold on Manhattan into a collection of settlements that far surpassed the small homeland they left behind. They named the colony New Netherlands. It was governed by a network of extremely wealthy landowners, called patroons, who had been granted large plots of land to cultivate and oversee. 

The Dutch Way

Originally, these patroons had the right to establish courts and levy taxes. Changes occurred when the British arrived in the late 17th century, and by 1775, the patroonships were abolished and renamed estates. By then, a sizable middle class had grown from Long Island and Manhattan, along the Hudson and Mohawk Rivers. Many had crossed the Hudson and settled along the Hackensack River in East Jersey. The cultural and economic influence of the Dutch still affected the renamed colony of New York, and they played an important role in the War for Independence.

Roots Deep and Wide

Philip Schuyler was born into a wealthy Dutch patroon family on November 20, 1733, in Albany, New York. His parents, Cornelia Van Cortlandt and Johannes Schuyler Jr., had extensive connections to the most prosperous patroon families. His maternal grandfather was Stephanus Van Cortlandt, the 17th Mayor of New York City. Educated by tutors at the Van Cortlandt family estate in New Rochelle, he mastered Mathematics and French, in addition to his native fluency in Dutch and English. Young Schuyler actively traded with the Indians and built strong bonds with the leaders of the nearby Iroquois of the Mohawk nation. He became fluent in their language.

First Fight

Like many of his generation, he gained military experience during the French and Indian War, where Schuyler served as a captain in the New York militia. His cousin, Lieutenant Governor James Delancey, had appointed him. His connections were extensive. The wealthy young Schuyler raised a local company. He participated in some of the key battles in upper New York, including Lake George, Oswego River, Carillon, and Fort Frontenac. At Oswego, he served as a quartermaster until the fort fell to the French.

Prosperous Patroon

Post-war, he built on his wealth as a patroon until he became one of the wealthiest and most prominent men in New York. In 1768, he parlayed his wealth and influence into a political career and secured a seat in the New York legislature. Although not a radical Son of Liberty, Schuyler spoke out against British policy. He managed to get himself on a commission to settle a boundary dispute with New Hampshire. This would earn him enemies among the New Hampshire and Massachusetts elites—enemies who would pursue him in years to come.

Philip Schuyler

Continental Congress

At the start of hostilities with Britain in April 1775, Schuyler served as a delegate to the Second Continental Congress in Philadelphia. His experience in the French and Indian War helped him on a committee that developed rules and regulations for the new United Colonies Army. This led to a friendship with General George Washington, who later asked Congress to appoint him as one of the Army's major generals. 

Continental Congress

All In

Despite his wartime experience, his appointment was more about securing New York's support for the Cause than leveraging his military skills. This kind of regional quid pro quo was common and used to ensure that the different colonies were "all in." Virginia's Colonel George Washington had edged out Massachusetts' John Hancock as commander-in-chief of the Army for the same reason.

John Hancock

First  Command

Schuyler's background and experience with upper New York made him a natural choice to command the Northern Department, headquartered in Albany, his old stomping grounds. However, the mission was daunting – assemble an army and invade Quebec (Canada), where it was expected that the local "Habitants" (French settlers) would rally to the Cause. His first move, however, was political. Schuyler managed to secure the neutrality of the powerful Iroquois Confederation – or at least delay their involvement.

Schuyler leveraged strong Iroquois connections

Quebec Disaster

While thus engaged, Brigadier General Richard Montgomery gathered the forces and began his advance without awaiting Schuyler's approval. Faced with a fait accompli and debilitated by a gout attack, Schuyler approved Montgomery's plans and set to work on the logistics support the fiery Irishman would need. The campaign started late in the season, so although initially successful, it collapsed in the depths of December when Montgomery and Benedict Arnold were cut down while storming Quebec City. Montgomery died, but Arnold recovered. Schuyler's New England foes quickly cast blame on the old Dutchman.

Night Assault of Quebec

Defending the North

The British, properly reinforced, launched an offensive in the spring. While Schuyler once again managed political interference, gathered men and supplies, and coordinated the overall effort, General John Sullivan, who fought a desperate retreat from Canada, attempted to garrison the mighty Fort Ticonderoga – The Gibraltar of the North.

John Sullivan

A British fleet gathered at the mouth of the Richelieu River, so Schuyler instructed Benedict Arnold (who had recovered from his wounds at Quebec) to take command of the forward defenses on Lake Champlain. The next phase of America's struggle would be fought on that long, icy body of water. Schuyler instructed Arnold to assemble a fleet to stop the armada of men and boats coming from the north under General Guy Carleton, Governor-General of Canada.

Lake Champlain Basin

Arnold performed a "rock soup" miracle, gathering a small flotilla of gunboats and, using his unique and aggressive cunning, surprised the fleet at Valcour Island. He fought the larger British ships bravely, but the Americans were torn apart by the heavier guns and ships. Still, the stubborn resistance slowed Carleton's advance, and since it was now October, he withdrew to winter quarters, planning to finish the campaign in spring 1777. The Americans had bought some time.

American defeat at Valcour Island 

Winter of Discontent

Schuyler was distracted from his preparations by a winter of bitter political infighting as his New England detractors blamed him for the northern failures. General Horatio Gates replaced him in March 1777, but the New York delegation in Congress raised a ruckus, and Schuyler was reinstated shortly afterward. However, the bitter infighting continued even as Schuyler worked to bolster Ticonderoga and begged his New England foes for more regiments to face the British onslaught forming in Canada.

Gibraltar of the North

By Land and Sea

Despite Schuyler's efforts to prevent another British advance, General John Burgoyne's 8,000-strong force sailed down Lake Champlain and moved uncontested into Fort Ticonderoga. Its commander, General Arthur St. Clair, realizing his forces were too weak to fight and would only be captured by the British, evacuated hours before the British arrived – a crucial decision. Schuyler approved St. Clair's withdrawal and ordered a "Fabian Defense." The garrison vanished into the thick woods, cutting down trees and constructing abatis and other obstacles in an effort to slow Burgoyne's troops, who were hot on their heels. The British were drawn deeper into the wilderness and away from the waterways that supplied their route south and their supplies.

Arthur St. Clair

Rallying the Militia

The Americans distracted the British, causing Burgoyne's advance to slow down and giving time for the militias to finally respond to Schuyler's call for men. British efforts toward New England and reports of Iroquois raids helped fuel this. From his headquarters in Albany, Schuyler made urgent pleas for powder, lead, guns, and supplies. But mainly, he needed men. His plans included establishing another line of defense about 30 miles north of Albany. 

Major General Schuyler

But the blame for Ticonderoga fell on Schuyler, and General Horatio Gates was once again put in charge. Gates halted the British in two decisive battles near Saratoga, where he accepted their surrender in October 1777.

Horatio Gates

Court Martial and Politics

Schuyler demanded and received a court-martial in 1778, which cleared him of wrongdoing, but he resigned his commission and returned to Congress in 1779. Philip Schuyler's legacy was that he was the only major general in the Continental Army never to fight a pitched battle. He continued to offer advice to his friend, General Washington, as his understanding of strategy and logistics was well recognized. His knowledge of Indian affairs also benefited Washington, who sought his counsel during the 1779 campaign against the Iroquois.

General Washington valued Schuyler's counsel

Enemy of the British?

Despite rumors in New England labeling him a Tory, Schuyler was targeted by the British. He faced the threat of personal attack. In October 1777, General John Burgoyne's retreating forces burned down Schuyler's country home. He later rebuilt it, and now it is open to the public. 

Schuyler's Estate Home rebuilt 

In another incident in 1780, British agents attacked Schuyler's Albany mansion under cover of darkness. The attempt, whether kidnapping or murder, was thwarted. Following the incident, Schuyler was under the protection of a bodyguard of Continental Army soldiers. However, he remained a target. On 7 August 1781, Schuyler foiled a kidnapping plot led by John Walden Meyers. It failed when Schuyler managed to escape from his Albany mansion. The Albany mansion served variously as his home, Northern Army headquarters, political center, and business office.

Schuyler Mansion in Albany

Post-War and Politics

The old patroon had powerful New York connections, and after the war, he focused on local politics by serving in the New York State Senate. He also served as a delegate to the state Constitutional Convention in 1789 and worked hard to support the new American Constitution. Schuyler was both a businessman and a soldier plus a politician. He expanded his estate near Saratoga after the war, growing to tens of thousands of acres, with a dozen slaves and tenant farmers, as well as a store and mills for flour, flax, and lumber. To get his goods down the Hudson River to market, he built schooners, naming the first Saratoga.

Schuyler had his own fleet

Federalist

Unsurprisingly, Schuyler was among the first two U.S. Senators appointed to represent the state in the new Congress. Naturally, the longtime ally of George Washington now supported his president as a steadfast Federalist. He especially backed the solid economic policies proposed by Secretary of Treasury Alexander Hamilton, who had married Schuyler's daughter, Elizabeth (more about her below). The whirlwind of New York politics caused him to lose his seat in 1792 but regain it in 1797. At the time, state legislatures, not the voters, elected senators — connections often determined who stayed or went. Schuyler was the first New Yorker to join the controversial Society of Cincinnati, a fraternity of Revolutionary War officers seen by some as a rising aristocracy. Yet most senior officers, including George Washington, had joined the organization.

President George Washington

Domestic Life

Schuyler married into the highly wealthy and influential Van Rensselaer family when he took Catherine Van Rensselaer's hand on September 7, 1755, in Albany. They had a large family of 15 children, eight of whom survived to adulthood. His second child, Elizabeth, later married young Continental Army officer Alexander Hamilton. She gained modern fame through the musical Hamilton. During her life, she used his legacy and family connections to participate in philanthropic efforts, including establishing the first orphanage in New York City.

The Hamiltons

Old Patroon

Schuyler's poor health led him to resign from political life in 1798. He died at his home in Albany in 1804, leaving a complex legacy of both success and failure. His critics saw him as too cautious or reserved to fight. Some accused him of treason—especially his enemies in New England—who were constantly suspicious of his aristocratic Dutch background. Regional conflicts also influenced perceptions. They believed Schuyler supported his own New York land claims over those of Vermont. Ironically, Schuyler later backed the Vermonters, which angered influential New York Governor George Clinton. Fame, wealth, and power drew powerful enemies to the Old Patroon.

Schuyler Grave and Memorial

Albany Rural Cemetery