Quebec: 31 December 1775
Swirling snow shattered the cold night’s darkness. Desperately cold and weary men stood in the courtyard, their nervous eyes scanning the dark walls for the enemy they knew was waiting. Their leader stepped forward. Eyeing a two-story blockhouse blocking their way, he had no time to lose, nor any hesitation. He drew his sword and led the troops toward it, shouting, "Come on, my good soldiers, your general calls upon you to come on."
First Fallen
The Continental Army lost several general officers in or directly because of combat during the American War for Independence. Generals High Mercer, Johann de Kalb, and Kazimierz Pulaski often come to mind. David Wooster not so much. And one, Major General Joseph Warren, surprisingly fell serving as a private soldier at Bunker Hill in 1775. Although Warren was a militia general and not leading troops, he still deserves to be named. But who was the first American general to fall while leading a group of American troops?
Son of Ireland
Not surprisingly, considering the timing, we are in the month of the Feast of Saint Patrick. He was a son of Ireland named Richard Montgomery. Born in Swords, County Dublin, Richard Montgomery was born into Ulster-Scots privilege on December 2, 1738. His family roots traced back to Donegal, but his branch of the Montgomery clan was now rooted in the Dublin-London connection. His father served as a member of parliament. His brothers also pursued the common British path of politics and military service. Young Richard followed that path as well, but with some interesting twists and turns along the way. Like many of his class, he entered Trinity College in Dublin but left before graduation to accept a commission in the 17th Regiment of Foot, purchased by his father in 1756. And why not? What better way to make a name for himself and advance than by following the colors?
Fighting France
The French and Indian War (Seven Years' War) served as the training ground for Montgomery, just as it did for many others on both sides who later fought in the American Revolution. Ensign Montgomery was about to embark on a whirlwind of action and adventure. His regiment was shipped to Halifax, Nova Scotia, where it joined a large British army preparing for the siege of Louisbourg, a fortress on the Atlantic coast of Cape Breton Island. This massive fort had played a key role in every struggle for North America. Now, two of Britain’s top generals, James Abercromby and Jeffery Amherst, had the forces to do it. On June 8, 1758, the attack began. Montgomery landed on the beach under heavy fire and ordered his troops to advance with fixed bayonets. The French outposts were overrun, and the siege commenced. The siege was successful, and General Amherst was impressed by Montgomery's actions during it, promoting him to lieutenant.
Struggle for New York
The Louisbourg campaign was followed by intense fighting in the wilds of central New York the next month, with the 17th and Montgomery deeply involved. The waterways—Lake Champlain and George, the Richelieu, and the Hudson, as well as the Mohawk Rivers—served as a strategic route through the mountains between central New York and Canada. Fans of "The Last of the Mohicans" can appreciate the setting: rugged slopes, large, dark, and deep lakes, swollen rivers, and lush valleys. The key fortifications of Fort Carillon (Ticonderoga) and Crown Point became focal points of deadly conflict. Still, it was a beautiful place where men blasted and carved each other to pieces. Montgomery’s skills were sharpened here; he learned patrols, picketing, and close combat.
The British eventually forced the French to retreat to the northern tip of Lake Champlain, gaining a strategic advantage. The 17th regiment spent 1759 in the Mohawk Valley under General Monkton’s command, who appointed Montgomery as adjutant on May 15—marking his distinction and potential. In August 1760, the 17th regiment moved toward Montreal as part of a three-pronged effort to capture the city. Montgomery’s regiment seized Isle aux Noix and Fort Chambly, then joined British regiments outside Montreal, which the Marquis de Vaudreuil, Canada's French governor, soon surrendered. However, the war was far from over.
French West Indies
The fall of Montreal gave the British control of North America, so they could now focus on the West Indies, where valuable sugar islands awaited. The 17th regiment sailed south after securing Canada. There were French and Spanish islands to conquer. The British took a beachhead on the key French island of Martinique and then launched an attack that overwhelmed the French outer defenses. The French survivors retreated into the capital, Fort Royal. This time, before the British could even start an attack, the French surrendered. The remaining French islands in the French West Indies—Grenada, Saint Lucia, and Saint Vincent—quickly followed. On 6 May 1762, Lieutenant Colonel John Campbell promoted Montgomery to captain and assigned him command of a company in the 17th.
Fighting Spain
Pontiac's War
Things did not quiet down in North America after France’s surrender. Angered that the French ceded their lands to the British and the land-hungry colonists, the tribes erupted into action in April 1763. The Ottawa chief, Pontiac, organized 18 tribes in a wave of attacks on British military and civilian settlements. Eight British forts fell, and two more were abandoned. General Amherst ordered the 17th to Albany in June 1763 to help fight the outbreak of hostilities. This would bring experience in Indian fighting and, more importantly, the start of a lifelong passion.
Romantic Interlude
Sailing up the North River to Albany, Montgomery’s vessel ran aground near Clermont Manor, NY, home of the influential Livingston family. The family entertained the ship's officers while their ship was being repaired. This was fortunate for the bachelor Montgomery, who met Janet, the 20-year-old daughter of wealthy and powerful Robert Livingston. It’s unclear if love blossomed at first sight, but Janet noticed Montgomery was not with the same group of officers when they returned to New York after the campaign. Clearly, the young Irishman made an impression.
Indian Fighter
The 17th spent 1764 on garrison duty at Fort Stanwix. While there, Montgomery requested leave from Colonel Campbell and General Thomas Gage to return to England for recovery from ill health caused by service in the Indies. Gage approved his leave, but only after the upcoming expedition.
In July, Montgomery’s regiment joined John Bradstreet’s expedition to Fort Niagara, providing security for Royal Indian Agent Sir William Johnson’s conference with the Great Lakes tribes. By August, the regiment was marched through woods and fields to Fort Detroit, the target of Pontiac’s attacks. Montgomery’s company was assigned to work on moving earth, logs, and stone to strengthen the beleaguered fort’s defenses. His leave was still on hold.
The following month, Montgomery received a break when General Bradstreet took him to Sandusky for a meeting with the Shawnee and the Delawares. After successful negotiations with the Iroquois, Bradstreet released Montgomery, who was then tasked with delivering dispatches to Gage before heading to England. Back in London, Montgomery soon became involved in political circles.
English Interlude
His health having improved, he associated with Whig Members of Parliament, who generally supported the colonists in their demands for more political freedom. Several of their prominent figures, Isaac Barre, Edmund Burke, and Charles James Fox, befriended the young officer. Political discussions with these and others led him to question government policies. When the 17th Foot returned to England in 1768, he was tasked with recruiting men to replace those lost to war and disease. Montgomery also experienced romantic disappointment when an arranged engagement ended because his fiancée proved unfaithful.
After months and years of active service, the dull routine of the peacetime army often aggravates ambitious men. Montgomery was no exception. In 1771, he discovered he was passed over for a promotion, possibly because of his Whig politics. He sold his commission for about £1,500 in 1772 and set sail for America in July. Spurned by a woman and the army, Montgomery had sworn to never marry or take up arms again. His goal was to become a gentleman farmer in the New World.
Colonial Life
Montgomery settled in a part of America he knew well: New York. Perhaps recalling his time on the Hudson, Montgomery rekindled his relationship with the wealthy young Janet Livingston. He purchased a farm at King's Bridge, 13 miles north of New York City. As he adjusted to his surroundings, Montgomery's "renewed acquaintance" blossomed into something more. Janet later recalled that his "politeness led him to make me a visit." The courtship led to an engagement, and by the following July, the confirmed bachelor found himself in wedded bliss.
Honeymoon on Hudson
Montgomery leased his farm to a tenant and moved into a cottage gifted to them by Janet’s grandfather, Judge Beekman. The cottage was located on the Post Road in Rhinebeck. Montgomery bought some of the nearby lands and started building the farmstead and laying the groundwork for a larger home called "Grasmere." Montgomery told Janet he was never happier but believed it couldn't last. For her part, Janet had a dream in which Montgomery was killed in a duel by his brother. He was determined to enjoy their brief happiness and insisted it be left to God. So, the couple enjoyed their happiness. But not for long.
Times of Upheaval
As the colonies started to question Parliament’s authority, political unrest shifted to resistance. By 1775, Montgomery began to oppose the British government, which he saw as oppressive. Being connected to one of New York’s most patriotic families also helped. The former British Army captain now viewed himself as an American, not an Englishman.
Provincial Politician
In May, Montgomery represented Dutchess County in New York’s new Provincial Congress. Although Montgomery had not sought political involvement, he had quickly become a well-respected local leader and was obliged to attend the session in New York City, some 80 miles south of Rhinebeck.
At the first session in May, Montgomery joined the other 97 delegates in approving a resolution legitimizing its authority. Yet he was still only a “moderate" patriot. Although he viewed the British Government as wrong in its policies, he still wanted honorable reconciliation. But the faction still loyal to George III was on the wane. Few of those delegates even showed up. But Montgomery stayed. He would fight for his rights as a Briton and an American. Due to his military experience, Montgomery was appointed to a committee tasked with planning defense works around New York and organizing and supplying the new provincial militia.
War for Independence
After George Washington was appointed Commander-in-Chief of the newly formed Continental Army on June 15, 1775, the Second Continental Congress asked the New York Provincial Government to select two men for service in the army. One would be a major general, and the other a brigadier general. The assembly favored the wealthy and well-connected Philip Schuyler as the major general, despite his lack of military experience. The more highly qualified Montgomery was made a brigadier general. Montgomery expressed reluctance to return to military life. Perhaps his premonition returned to haunt him, but he agreed to serve.
Montgomery's thoughts on serving are expressed in a letter, "The Congress having done me the honor of electing me brigadier-general in their service, is an event which must put an end, for a while, perhaps forever, to the quiet scheme of life I had prescribed for myself; for, though entirely unexpected and undesired by me, the will of an oppressed people, compelled to choose between liberty and slavery, must be obeyed."
America Turns North
In June 1775, newly proclaimed commander-in-chief General George Washington appointed Montgomery as deputy commander under Philip Schuyler, who received orders to invade Quebec and bring Canada into the war on the American side. A force was assembled at Fort Ticonderoga, and Schuyler left to take command of the army, leaving Montgomery in Albany to make final arrangements for the invasion. Janet followed him as far north as Saratoga, where he promised he would do his duty and preserve his honor.
Plans, Logistics, and Delay
Schuyler spent the summer preparing for the invasion. By this time, Washington decided to send Colonel Benedict Arnold to lead another force to invade Quebec from Maine and join Schuyler's army outside Quebec City. Schuyler entrusted most of the tedious military administration to Montgomery. Instead, he focused on politics, which was his strong suit. Schuyler pushed for more men and supplies and negotiated to keep the Iroquois neutral during the campaign.
A Time for Action
Meanwhile, Montgomery, upon receiving intelligence that the British were preparing to station armed vessels on Lake Champlain, quickly headed north to confront the threat. Without seeking permission from Schuyler, he sailed up the lake with 1,200 men. Montgomery sent a dispatch to Schuyler explaining the situation. He recognized that the season for war was ending, and time was not on the American side.
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