Major William Montgomery

British OfficerAssault Commander

John Trumbull, 1786

Biography

Major William Montgomery

British Officer and Assault Commander at Fort Griswold

Little is known with certainty about the early life and personal background of William Montgomery before he appeared in the military records of the American Revolutionary War. Like many British officers of his era, he likely came from the professional military class or the minor gentry that supplied the Crown's armies with their leadership throughout the eighteenth century. The British Army of this period drew its officers from families with traditions of military service, and the rank of major suggested a man who had spent years working through the hierarchies of regimental life. Whether Montgomery had prior combat experience in earlier campaigns — in the European theater, in the Caribbean, or in the early years of the American conflict — remains unclear from surviving records. What is certain is that by 1781, he had risen to a rank that placed him in command of significant bodies of troops and made him a trusted subordinate for demanding field operations. The world he inhabited was one of rigid discipline, professional ambition, and an officer corps that valued personal courage in combat above almost every other quality. These values would carry him to the walls of Fort Griswold and to his death.

By the autumn of 1781, the Revolutionary War had entered a phase of increasingly desperate British strategic maneuvering along the American coastline. Major Montgomery was serving in the forces under the command of Brigadier General Benedict Arnold, the former Continental Army hero whose defection to the British in 1780 had made him one of the most notorious figures of the war. Arnold had been tasked with organizing a punitive expedition against the Connecticut coast, targeting the port of New London and the surrounding Thames River valley. The operation was designed to destroy military stores, burn shipping, and eliminate harbor infrastructure that supported American privateering — a thorn in the side of British naval operations. Montgomery's assignment to this force placed him at the center of a mission that was fundamentally destructive in character, aimed not at seizing and holding territory but at inflicting economic and military damage. His role would be specifically focused on the eastern bank of the Thames River, where Fort Griswold on Groton Heights represented the principal fortified position defending the approach. This was not a minor garrison action but a full-scale assault against prepared defenses manned by determined militia.

On September 6, 1781, Major Montgomery led the British assault force against Fort Griswold, a star-shaped earthwork fortification perched on the high ground overlooking the Thames River in Groton, Connecticut. The fort was garrisoned by Connecticut militia under the command of Colonel William Ledyard, who had rallied roughly one hundred fifty defenders when word of the British landing reached the surrounding communities. Montgomery's task was daunting by any measure: he had to advance his troops across open ground, uphill, against a fortified position whose defenders could pour concentrated musket fire into the approaching columns. The earthwork walls, ditches, and fraises — sharpened stakes angled outward from the walls — made the fort a formidable obstacle. Montgomery nevertheless pressed the assault with the aggressive determination expected of a British officer, driving his men forward through devastating fire that cut down soldiers in large numbers as they closed the distance. His decision to continue the attack despite mounting casualties reflected both personal courage and the professional ethos that demanded officers lead from the front. The advance was costly, but the weight of British numbers began to tell as the assault force reached the walls and began to breach the defenses.

The turning point came at the very moment when the British assault was on the verge of success. As Montgomery's troops fought their way over the walls and into the interior of Fort Griswold, Montgomery himself was killed in the breach. According to the tradition long preserved by the Groton community and its descendants, the man who struck the fatal blow was Jordan Freeman, a free Black defender who drove a spear or pike into the major as he crested the fortification's walls. This act of resistance at the critical instant became one of the most significant moments in the entire battle. Montgomery's death did not halt the British assault — the defenders were already being overwhelmed by superior numbers — but it transformed the character of what happened next. The loss of their commanding officer at the moment of victory sent a shock of rage through the British troops pouring into the fort. What should have been a conventional surrender became instead a massacre, as British soldiers killed defenders who had laid down their arms, including Colonel Ledyard, who was reportedly run through with his own sword after offering it in surrender.

The violence that followed Montgomery's death cannot be understood without examining the relationships among the officers and men involved. Benedict Arnold, who commanded the overall operation from the New London side of the river, bore ultimate responsibility for the conduct of his troops but was not physically present at Fort Griswold when the massacre occurred. The British officers who were on the scene — those who survived the assault and assumed command after Montgomery fell — either could not or did not restrain their men from killing the surrendering garrison. The loss of a senior officer in the heat of an assault created a dangerous vacuum of authority and discipline precisely when control was most needed. Colonel Ledyard's militia defenders, including Jordan Freeman and other men whose names have been preserved in local memory, had fought with a tenacity that earned them lasting honor but that also, under the brutal conventions of eighteenth-century siege warfare, placed them at risk of retaliatory violence. The unwritten rules of the era held that a garrison that forced an attacker to pay heavily and then attempted to surrender at the last moment could expect little mercy, though this custom never justified outright massacre.

The legacy of Major William Montgomery is inseparable from the atrocity his death helped unleash. He entered history not as a celebrated British hero but as a figure whose fall on the walls of Fort Griswold set in motion one of the American Revolution's worst war crimes. His name is remembered in Groton not with the honor typically accorded to fallen officers but as part of a cautionary narrative about the consequences of violence, the fragility of military discipline, and the thin line between battle and massacre. Montgomery's story also illuminates the courage of the defenders who opposed him, particularly Jordan Freeman, whose act of resistance in killing a British major became a powerful symbol of Black participation in the fight for American independence. For students of the Revolution, Montgomery represents a complex truth: that individual deaths in combat could have consequences far beyond the battlefield, shaping the moral narrative of an entire war. His story reminds us that the Revolution was not a clean or heroic affair but a brutal conflict in which the breakdown of restraint could turn a military engagement into a crime that haunted communities for generations.

WHY MAJOR WILLIAM MONTGOMERY MATTERS TO GROTON

Major Montgomery's story is central to understanding what happened at Fort Griswold on September 6, 1781, and why the battle became one of the Revolution's most tragic episodes. His death at the moment of British victory transformed a hard-fought assault into a massacre that killed scores of surrendering defenders and scarred Groton for generations. Students and visitors to Fort Griswold should know Montgomery's name because it connects them to the human chain of cause and consequence that defines real warfare — the killing of one man leading to the slaughter of many. His story also elevates the heroism of Jordan Freeman and the militia defenders who stood against professional soldiers, reminding us that the Revolution's meaning was forged not only in famous battles but in small forts on windswept heights above the Thames River.

TIMELINE

1781, September 4–5: Benedict Arnold assembles a British raiding force of approximately 1,700 troops for the expedition against New London and Groton, Connecticut
1781, September 6 (morning): British forces land on both sides of the Thames River; Montgomery is assigned to lead the assault on Fort Griswold on Groton Heights
1781, September 6 (midday): Montgomery advances his troops against Fort Griswold under heavy fire from Colonel William Ledyard's militia garrison
1781, September 6: Montgomery is killed during the breach of Fort Griswold's walls, reportedly by defender Jordan Freeman wielding a spear or pike
1781, September 6 (aftermath): British troops, enraged by Montgomery's death and their heavy casualties, massacre surrendering defenders inside the fort
1781, September 6: Colonel William Ledyard is killed after offering his sword in surrender; approximately eighty defenders are killed or wounded after resistance ceases
1830: The Groton Monument is erected on the site to honor the fallen defenders of Fort Griswold

SOURCES

Caulkins, Frances Manwaring. History of New London, Connecticut: From the First Survey of the Coast in 1612 to 1860. H.D. Utley, 1895.
Decker, Robert Owen. The Whaling City: A History of New London. New London County Historical Society, 1976.
Connecticut Society of the Sons of the American Revolution. The Battle of Groton Heights: A Collection of Narratives. Acorn Club, 1882.
Fort Griswold Battlefield State Park. Interpretive materials and historical documentation. Connecticut Department of Energy and Environmental Protection. https://portal.ct.gov/DEEP/State-Parks/Parks/Fort-Griswold-Battlefield-State-Park

In Groton

Sep
1781
Battle of Fort Griswold
Role: British Officer
# The Battle of Fort Griswold By the autumn of 1781, the American War of Independence was entering its decisive phase. In the south, General George Washington and his French allies were maneuvering toward what would become the siege of Yorktown, a campaign that would effectively end major combat operations in the war. Yet even as the British position grew increasingly precarious, the conflict continued to exact a devastating toll on communities throughout the colonies. One of the war's most tragic episodes unfolded on September 6, 1781, along the banks of the Thames River in southeastern Connecticut, when British forces launched a coordinated assault on the towns of New London and Groton. The attack was led by none other than Benedict Arnold, the former American general whose name had already become synonymous with treason. Arnold, a Connecticut native who had defected to the British the previous year, knew the region intimately, and the Crown exploited that knowledge by placing him in command of a force of approximately 1,700 troops tasked with destroying American privateering operations and the supplies stored along the river. Arnold divided his forces into two columns. He personally led the assault on New London, on the western bank of the Thames, where his troops burned much of the town and destroyed warehouses filled with goods captured from British merchant ships. Meanwhile, approximately 800 British soldiers crossed the river to attack Fort Griswold, a stone-walled fortification perched atop Groton Heights on the eastern bank. The fort was garrisoned by roughly 150 local militia under the command of Colonel William Ledyard, a respected community leader who understood that his small force faced overwhelming odds but resolved to defend the position nonetheless. The terrain favored the defenders, and the stout walls of the fort provided meaningful protection, but the sheer disparity in numbers meant that the outcome, barring relief or retreat, was likely predetermined. The British assault proved far costlier than the attackers had anticipated. The militia defenders fought with remarkable determination, repulsing two full-scale assaults and inflicting severe casualties on the advancing British columns. Among those killed during the fighting was Major William Montgomery, a British officer who fell while leading his men against the fort's walls. On the third attempt, however, the British finally breached the fortifications and poured inside. What followed has been remembered as one of the darkest moments of the Revolutionary War. Rather than accepting the surrender of the garrison, many of the British soldiers, enraged by the fierce resistance and the heavy losses they had sustained — approximately 200 killed and wounded — turned on the defenders even after organized resistance had ceased. Colonel Ledyard, recognizing the hopelessness of further combat, reportedly offered his sword to a British officer in the customary gesture of formal surrender. According to accounts that have persisted since that day, the officer took the sword and ran Ledyard through with it. The killing did not stop there. Approximately 85 American defenders were killed in the battle and the massacre that followed, and some 60 more were wounded, many of them gravely. The survivors were loaded onto a cart to be transported downhill, but the cart reportedly broke free and careened down the slope, compounding the suffering of the already broken men. The events at Fort Griswold sent shockwaves through Connecticut and the broader American public. The massacre of soldiers who had already surrendered violated the accepted rules of warfare and fueled outrage that only strengthened colonial resolve. Benedict Arnold's role in directing the operation against his own home state deepened the contempt in which he was already held. For the communities of New London and Groton, the raid was a catastrophe — homes and livelihoods were destroyed, and nearly every family in the area lost someone in the fighting. In the larger story of the Revolution, the Battle of Fort Griswold stands as a somber reminder that the war's final chapter was written not only in the grand maneuvers at Yorktown but also in the blood of ordinary citizens who took up arms to defend their homes. Just weeks after the massacre on Groton Heights, Cornwallis surrendered his army in Virginia, effectively ending the war. The men who died at Fort Griswold never saw that victory, but their sacrifice became a lasting symbol of the cost of American independence. Today, the Groton Monument, a granite obelisk erected on the site of the battle, bears the names of those who fell, ensuring that their story endures for future generations.
Sep
1781
Jordan Freeman Kills Major Montgomery
Role: British Officer
**The Battle of Fort Griswold and the Courage of Jordan Freeman** On September 6, 1781, the coastal town of Groton, Connecticut, became the site of one of the most brutal engagements of the Revolutionary War. The assault on Fort Griswold, led by British forces under the broader command of the infamous turncoat Benedict Arnold, resulted in a fierce and bloody confrontation that would claim the lives of dozens of American defenders. Among those who fought and died that day was Jordan Freeman, a free Black soldier whose act of defiance against a charging British officer became one of the most striking moments of the battle and a powerful symbol of the diverse coalition of Americans who took up arms in the fight for independence. The attack on Groton and the neighboring town of New London was part of a British effort to destroy supplies and disrupt American operations along the Connecticut coast. Benedict Arnold, once one of the Continental Army's most talented generals before his betrayal of the American cause, led approximately 1,700 British troops in a raid targeting the ports and storehouses of the region. While Arnold personally directed the burning of New London on the west side of the Thames River, a detachment of British regulars crossed to the eastern bank to assault Fort Griswold, the primary defensive fortification protecting Groton Heights. The fort was garrisoned by a relatively small force of local militia, men drawn from the surrounding communities who had assembled hastily to defend their homes. Among them was Jordan Freeman, a free Black man who served alongside his white neighbors in the militia ranks. The British force that attacked Fort Griswold was led in part by Major William Montgomery, an experienced officer who commanded one of the columns tasked with storming the fortification's walls. The defenders, though outnumbered, put up a determined resistance, pouring musket fire and cannon shot into the advancing British troops as they crossed the open ground surrounding the fort. The fighting was intense and came at great cost to the attackers. As Major Montgomery attempted to scale the walls of the fort during the assault, Jordan Freeman reportedly confronted him directly and killed him with a spear, striking down one of the most prominent British officers on the field. Montgomery's death in the act of breaching the defenses was a dramatic moment in a battle already marked by extraordinary violence. The fall of Major Montgomery and the heavy casualties suffered by the British during the assault may have contributed to what happened next. After the garrison eventually surrendered, British soldiers carried out acts of retaliatory violence against the American defenders, killing many who had already laid down their arms. The massacre at Fort Griswold became one of the most notorious episodes of the war, fueling outrage throughout Connecticut and the broader American cause. Jordan Freeman himself did not survive the battle. He was killed during the fighting, giving his life in defense of the fort and the ideals of the Revolution. Freeman's sacrifice, and his presence on the battlefield, speaks to a reality of the Revolutionary War that is sometimes overlooked. The forces that fought for American independence were not monolithic. Free Black men like Jordan Freeman served in militia units and Continental forces throughout the war, contributing to a cause whose promises of liberty and equality were not yet extended to all. Freeman's name is inscribed on the Groton Monument, a tall granite obelisk erected on the site of Fort Griswold to honor the defenders who fell there. His inclusion alongside the other names on the monument is a recognition that his service and sacrifice were equal to those of any other soldier who fought and died that day. The Battle of Fort Griswold and Jordan Freeman's role in it matter not only as a chapter in the military history of the Revolution but as a reminder of the complex and often contradictory nature of the founding era. Freeman fought as a free man for a nation still grappling with the institution of slavery, and his courage in the face of a determined enemy deserves to be remembered as part of the full and honest story of American independence.