First to Fall Part 2: First Hero

Autumn Winds

Brigadier General Richard Montgomery tugged at his leather glove as the line of poorly fed and poorly armed men marched northward. The winds were strengthening, and the skies looked like slate. His eyes shifted to the dense forests to the north – Canada. We must strike quickly, or these lads will leave their bones here. 

Brigadier General Richard Montgomery

Isle of Hope

On September 4th, Schuyler joined Montgomery with an additional 800 men. Now, he had 2,000 poorly trained and poorly equipped soldiers. Schuyler was also ill. Despite this, the aging New Yorker ordered the army to move toward a small island on the Richelieu River called Île aux Noix. With little time left, on September 6th, Montgomery led a force north to their first goal, Fort St. John's, which protected the route to Montreal. Paddles and oars brushed the dark waters, each stroke bringing the army and Montgomery closer to their destiny. They carried more than just bullets in their pouches. Schuyler, who was in poor health and unable to lead the expedition, had drafted a proclamation calling the Canadians "Friends and Countrymen" and pleading for their support in driving the British out of the territory. They would be disappointed in this hope. Montgomery’s probing attack failed. Although he managed to repel an ambush of about 100 Indians under Captain Matthew Mead, Schuyler feared the fort couldn't be taken by storm and ordered Montgomery to return to the island, which the Americans then fortified.

Area of Operations around Montreal

Fort St. Johns 

Montgomery decided to make another attempt at Fort St. Johns, but this attack was no more successful. In a series of errors, the two pincers of the American assault collided in the dark, muddy woods. Each thought they had encountered the British, and both forces fled. A furious Montgomery was able to stop the retreat and redirect them toward the fort.

His men advanced under withering British grapeshot fire, and the assault on the British breastworks was driven back. Montgomery planned another attack on the fort. However, half the New England troops fled. Montgomery, believing his force could no longer take the fort, retreated to Île aux Noix. When Schuyler’s illness forced him to return to Fort Ticonderoga, command of the late-start and ill-equipped operation was now his.

On September 16, Montgomery launched another expedition against the British fort. This time, he had 1,400 men along with a naval component consisting of two small ships and ten bateaux carrying 350 troops. The bateaux would counter the HMS Royal Savage. Montgomery arrived with the main force the following day. A month-long siege began, with the defenders outmanned and the attackers outgunned. The British garrison of 725 men was commanded by Major Charles Preston, who had been Montgomery's superior officer in the British Army just three years earlier. After initial skirmishing, Montgomery proceeded to besiege the fort. Progress was slow. Montgomery was everywhere at once, encouraging the building of siege lines and often coming under fire himself. 

                                                                        Fort St. John

On September 22, the fiery general was inspecting the breastworks when a cannon shot from the fort flew by, tearing his coattails and causing him to tumble down. By luck and skill, Montgomery managed to land on his feet. His men watched and were all impressed by his Sang Froid. Their commander was a man of steel nerves. However, by early October, they still had not closed the ring on the fort, despite bringing in more guns. One battery did sink HMS Royal Savage, but Montgomery’s forces remained outgunned in most areas. 

In mid-October, James Livingston, a relative of Janet Montgomery, recommended that Montgomery attempt to attack nearby Fort Chambly, which was a weaker post than St. John. He agreed and launched a night assault ten miles down the river. In two days, the fort surrendered 83 men and a large amount of valuable powder. However, the most significant prize was the colors of the 7th Royal Fusiliers, which he sent to the bedridden Schuyler – marking the first time a British battle flag fell into American hands.

The King's Colors of the 7th Royal Fusiliers

This boosted morale, and Montgomery was able to get his men to reinforce the defenses around Fort St. John. They also managed to repel a relief force sent from Montreal by General Guy Carleton, the British commander in Canada. By November 1st, the new batteries positioned north of the fort completed the encirclement. They launched a bombardment that shattered walls and buildings, causing little damage but significantly lowering the defenders' morale. As night fell on the battlefield, Montgomery ordered a cease-fire and sent a flag of truce. During the night, the Americans intercepted a dispatch from Carleton instructing Major Preston to continue his defense. The following day, the fort surrendered with full military honors, and its garrison marched off to imprisonment. One can't help but wonder what might have happened if the message had gone through. 

Montreal

Montgomery’s first major victory was now within his reach. But the weather and the terrain proved to be tough allies for the British. His men trudged across rugged ground covered with ice and snow. An early winter storm made progress even harder. He encouraged his men forward, knowing Carleton and his army were nearly cornered. When he learned of a British attempt to escape, he sent a detachment to Sorrel. After brief fighting, the British withdrew. Smoke rising from Montreal's chimneys welcomed Montgomery’s troops as they approached the city. A surrender demand failed, however, and as negotiations dragged on, Carleton managed to slip down the St. Lawrence River to the safety of Quebec. On November 13, Montgomery’s exhausted men entered a city without defenders - a Pyrrhic victory. 

Guy Carleton

 Back in Montreal, Montgomery insisted that the captured British prisoners be treated kindly. After all, many of them were not long before his comrades in arms. However, some of his own officers were unhappy with this. Montgomery was disappointed by another act of indiscipline, and only protests from the commander-in-chief prevented him from resigning.

Quebec

Determined to finish the campaign, Montgomery sailed to Quebec City on November 28 with 300 of his best men. Four days later, he joined forces with Benedict Arnold's remaining men at Pointe aux Trembles, just upriver from Quebec. Montgomery took command of both groups, and his first action was to deliver much-needed clothing and supplies to the exhausted “rabble in arms” marching through the Maine wilderness. But winter was tightening its grip on Canada, forcing him to act swiftly. The next day, his combined force moved downstream and encircled Quebec. On December 7, he sent a letter with an ultimatum, but it was burned by Carleton. Montgomery then tried to win the Canadians over to the cause, but his envoy was arrested. Desperate to reach Les Habitants (the locals), he had his proclamation shot over the city wall with bows and arrows. However, they stayed loyal to their new rulers.

Quebec City was the Key to Canada

Now Montgomery had to do the tough work of a siege. Several mortars began shelling the city, but their shells caused little damage. Undeterred, Montgomery moved another battery onto the Plains of Abraham, the site of the battle that decided the city's fate in the French and Indian War. The guns were closer to the walls but also more exposed. Still, by December 15, Montgomery had his batteries in position. Anxious for a resolution, he once again asked for Carleton’s surrender. When Carleton refused, Montgomery’s batteries opened fire. The guns failed to make an impact and were immediately threatened by effective British counter-battery fire. He was forced to order them back. 

Quebec City and Environs

With supplies running low, morale weakening, and winter approaching, Montgomery had no choice but to storm the city. He decided to attack the Lower Town district (Saint-Roch) on the bank of the Saint Lawrence while Arnold would assault the powerful Cape Diamond Bastion. He planned the attack during a stormy night, hoping the weather would conceal their movement from the British. An attack scheduled for December 27 was canceled when the weather cleared. He was forced to revise his plans after someone defected to the British and revealed his strategies.

Montgomery's situation required 

careful planning and flexibility

Montgomery prepared his plan. He aimed for a two-prong attack on the Lower Town, coming from the south, while Arnold would attack from the north. To mislead the British, Montgomery used a deception tactic. He ordered the 1st Canadian Regiment (local fighters who had joined the American cause) to fire at one of the gates, while a separate group engaged the defenders at Cape Diamond Bastion. The signal for the assault was rocket fire. Montgomery’s unimpressive artillery would bombard the city during the feint attacks. This was a bold and risky move. One Montgomery was reluctant to make, but he had no alternative. As George Washington would face a year later, expiring enlistments were draining the army, and many would be gone by January 1. 

A Night to Remember, and Forget

Montgomery experienced his second snowstorm on the night of December 30. He quickly issued the order. Shivering but now energized, the Americans gathered in the wind and snow. The night was cold, dark, and intense, with wind howling and snow swirling. Where was the signal? At 4 am, an orange burst lit up the sky. Boot steps muffled by the wind and snow as his men made their way to the lower town. However, the British were warned by the rockets, and the walls were well-manned. 

Night attack in a snowstorm

With their general at the front, the Americans edged down the steep and slippery cliffs and arrived just below the city walls. As if they didn't have enough obstacles, a palisade at the edge of the Lower Town now blocked their way! Axemen ran to the front and began chopping through. Then Montgomery personally led his column through the opening. Unknown to Montgomery, he was now a major general, promoted by Congress on December 9 for his victories at St. Johns and Montreal. Seeing a two-story blockhouse blocking their path, he had no time to waste or hesitate. He drew his sword and led the troops toward it, shouting, "Come on, my good soldiers, your general calls upon you to come on."

Quebec's defenders proved formidable

The desperate men gripped their muskets tightly and moved forward. About fifty yards away, an equally determined group of Canadian militia and British sailors in the blockhouse unleashed a barrage of musket balls and grapeshot. Montgomery was hit in the head and both thighs by grapeshot and died instantly. The deadly fire brought down two of his captains.

Death of Montgomery

The attack fell apart after Montgomery’s death. The Americans retreated chaotically. A staff officer named Aaron Burr tried to carry Montgomery’s body back but failed. Meanwhile, Benedict Arnold's attack, which had started well, also broke down when Arnold was wounded in the leg by a ball. Many of his men, including Daniel Morgan, were forced to surrender to the British bayonets. With the guns suddenly silent, the howling wind and snow marked the end of the effort to connect Canada to the American cause. 

Benedict Arnold

Honors in Death

Montgomery was highly respected by the British for his previous service and his humane treatment of prisoners at Montreal. Carleton had him buried modestly but with honor on January 4. Some of his men, now prisoners, watched their beloved and heroic general during the solemn funeral. Meanwhile, Arnold, with a bandaged leg, took command of the battered army. His efforts to save the lost cause would be heroic and extraordinary but ultimately futile.

First Hero – First Monument

News of Richard Montgomery’s death was a heavy blow to the Northern Department. Schuler wrote, "My amiable friend, the gallant Montgomery, is no more; the brave Arnold is wounded; and we have met a severe setback in an unsuccessful attempt on Quebec. May Heaven be graciously pleased that the misfortune may end here." For a time, news of his death was kept quiet to delay the morale decline that would follow.

Phillip Schuyler

Washington was dismayed at the loss. So struck by Montgomery’s valiant death, Congress commissioned a monument to him and held a memorial service. He was celebrated as a hero throughout the colonies – perhaps the nation’s first national hero. 

The Montgomery Monument

Significantly, Montgomery's death was mourned in Britain, and his former Whig allies used his death as an opportunity to criticize British policy. British Prime Minister Lord North acknowledged his qualities as a man but condemned him as a rebel. However, many of the London papers actually paid tribute to Montgomery. 

Lord North

Montgomery’s widow, Janet, dedicated her life to protecting his legacy. She moved to the house near Rhinebeck, which she had initially hoped to keep before the war. She also rejected a marriage proposal from former Continental general and British officer Horatio Gates. This was noteworthy in a society where widows usually remarried. 

Final Farewell

In 1818, Governor Stephen van Rensselaer of New York had Montgomery's body moved to New York. About 5,000 mourners participated in his funeral procession, and on July 8, he was laid to rest for the last time next to the Montgomery monument at St. Paul’s Church. The ceremony provided some closure for Janet Montgomery, who was pleased with the honors given to the soldier she loved.

In closing, Montgomery, Alabama, named after America's first hero, unveiled a statue of its namesake in 2019 as part of its bicentennial celebration. It is somehow touching that a man who died in the cold of the North would be honored by citizens in the deep South. 

Montgomery statue in Alabama

First to Fall: Richard Montgomery

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."

Richard Montgomery

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 Continental troops, he still deserves recognition. But who was the first American general to fall while leading a group of American troops?

Hugh Mercer: most celebrated

 fallen general

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 Jeffrey 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. 

Siege of Louisbourg

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, the Richelieu, the Hudson, and 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, which features 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. 

Fort Ticonderoga

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 withdrawing north on Lake Champlain

French West Indies

The fall of Montreal gave the British control of North America, allowing them to 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.

The British invasion of Martinique

Fighting Spain

Now Britain could turn against France's ally, Spain. Since Spanish Cuba controlled the approaches to the Indies and North America, it was a prime target. On June 6, British forces arrived off Havana's coast. Before them stood Moro Fort, the key to the Spanish defense of the city. It had to be taken. British battleships bombarded the fort, silencing all but two Spanish guns. On July 30, Captain Montgomery and the 17th Foot stormed and captured the fort. In late August 1762, Montgomery and the 17th Foot were sent to New York. The long and bloody war ended with the Treaty of Paris on February 10, 1763. At the time, the British triumph was resounding: a world empire! Few could have imagined that the treaty would lead to even more conflict, political unrest, and a longer war.

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.

Pontiac's War threatened Britain's new western lands

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 vessel 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.

Janet Livingston

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.

Ottawa War Chief Pontiac

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.

Sir William Johnson

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. Upon returning to London, Montgomery soon became involved in the city's political circles.

General John Bradstreet

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. 

Edmund Burke

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 that he had been passed over for a promotion, possibly due to 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.

Montgomery settled along the North (Hudson) River

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 purchased some of the nearby lands and began building the farmstead, 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 wedded bliss. But not for long.

The Montgomery Cottage

Times of Upheaval

As the colonies began to question Parliament’s authority, political unrest evolved into 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. 

Parliament

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. He was obliged to attend the session in New York City, some 80 miles south of Rhinebeck.

New York was rife with political strife

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.

Phillip Schuyler

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.

Albany, NY circa American Revolution

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 in invading Quebec from Maine and joining 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.

Colonel Benedict Arnold

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 side of the Americans.

Next Edition: Richard Montgomery’s War

Shores of Tripoli

 Review: Shores of Tripoli 

This is a rare and unusual Yankee Doodle Spies sequel segment. Although it’s a bit of a stretch, I felt compelled to review this board game because it depicts events that have some surprising links to the time of the Yankee Doodle Spies. What motivates me to review this game? In a word, fun. Shores of Tripoli offers an engaging and intriguing look at this pivotal period in United States national security policy. Players learn as they play and interact while they learn. And they have a good time. But I think I already mentioned that.

                                                           Poster of the 1950s Action Flick

Fort Circle Games

Kevin Bertram, designer and owner of Fort Circle Games, shares that his inspiration for the game came from Brian Kilmeade’s book about the American effort to suppress the Barbary (North African) States and their corsairs (pirates) at the start of the 19th century. I admit—I haven't read the book, though I’ve read others on the topic and watched the John Payne film, Tripoli, as a young person. In his designer notes, Kevin mentions he created the game after realizing no one had addressed this subject. I started playing board wargames when I was in third grade. The first I remember was called Tactics II. I played wargames for many years and even tried miniatures. After reading Kevin’s words, I agreed—he’s right. So, the game is groundbreaking for shining a light on that little-known conflict.

                                                                            Box Cover

The Mechanics

I'm not talking about Paul Revere’s spy network, but about how the game is played. I'll let others give a play-by-play of the rules. You can also find many YouTube clips by Kevin and other players who enjoy the game explaining the rules. 

https://www.youtube.com/watch?v=etnQr4eTy6s&fbclid=IwAR0gOquGCChbCxnXMEHmOIaQVudN7seQoFRStocsAS9QRL1K4SEUAFW11og

The game starts as a board game featuring a simple, attractive map of North Africa. Important ports like Gibraltar (British-controlled and neutral), Malta, Tripoli, Alexandria, and Derne are marked, as these are where most of the action takes place. Players move ship markers, including American, Swedish, and Tripolitan frigates; American cutters; and Tripolitan and allied corsairs. You also manage soldier markers such as US marines, Hamet’s (deposed older brother and rival to Tripolitan ruler Yusuf Karamanli) mercenaries, and Barbary pirates. 

                                                                Pieces, Dice & Board

Combat relies on die rolling, and this game involves a lot of it. Luck often outweighs skill in many situations. I think Napoleon once said he would prefer having a lucky general over a good one. However, the game is mainly driven by card play. Players draw cards from a deck each turn and can discard any card to make a move or play specific cards to bring in reinforcements or perform various actions. The real key is the Event Cards, which influence movement, combat, political actions, and more. Players constantly draw, discard, or play cards as the game unfolds across four seasons each year from 1801 to 1806. The cards bring surprises, both positive and negative. How a player uses the cards dealt to them can make up for poor dice rolls and mistakes. So, watch them closely. And may the odds always be in your favor.

                                            American Frigate takes on a Barbary Corsair

The Result

The game provides players with about an hour of fun and frustration. It's a two-player game featuring a cool solitaire option. The American side has many advantages, such as large ships (frigates), US Marines, and Swedish allies. Yeah — Sweden! But the American side also faces significant risks. Closing the deal, which involves assaulting and capturing Tripoli, can result in a Ragnarök-like end for the game. The American player starts slowly, building firepower with frigates and gunboats, while pesky pirates go on raids.

                                                            The cards make the game

The Barbary player has less firepower but more flexibility. He can run out the clock. If the American player is too cautious, the Barbary player may have time to launch enough raids to win by capturing treasure (gold-colored coins). Or he can win if the American fails to use the right mix of naval and land forces to take Tripoli. And though the American frigates are strong, they are also vulnerable: losing four of them wins the game for the Tripolitan side. This reflects how American and European public opinion reacts to unacceptable losses. A draw favors the Barbary States, but the Americans can use cards and clever maneuvers to force a treaty and secure victory.

                                                        USS Philadelphia under attack

Either way, both sides have fun and learn a lot about this important but little-known event in American history.

                                                            Jefferson's Letter to the Bey

The game features an intelligent historical supplement and designer notes that enhance the rules effectively. The design, artwork, and layout are of top quality. A highlight is the “mock-up” of the 21 May 1801 letter to the Pasha and Bey of Tripoli, Yusuf Karamanli, which explains the reason for the friendly visit of the American squadron to the Mediterranean. It creates an engaging scene with atmosphere as you read President Jefferson’s reassuring words. 

Yankee Doodle Spies Sequel?

The war against the Barbary States was the first effort by America to send military force overseas. One of the results of the American War for Independence and American sovereignty was losing the protection of the powerful British Navy. This was clear during the undeclared naval war with France, an event that led to the rebirth of an American naval force focused on a small fleet of "super-frigates," which served as fast and nimble ships-of-the-line.

Key figures – Rev War Connections

I'll now circle back to the American Revolution with some interesting links between the Tripoli affair and the era of the Yankee Doodle Spies.

                                    1st Lt Presley O'Bannon raises the American flag over Derna

Thomas Jefferson

The most prominent figure is President Thomas Jefferson, the central character in the event. The founding father and the first Secretary of State sought a peaceful way to handle the Barbary States’ demands for tribute—without actually paying it. This approach was influenced by the pride of a newly independent and still uncertain republic and limited funds. His letter dated 21 May 1801 was his last effort to negotiate. However, the Bey of Tripoli had already chosen war, declaring it on 14 May.

                                                            President Thomas Jefferson

William Eaton

William Eaton is one of those tough historical figures who played a major role in a key event. Son of a middle-class New England farmer, young Eaton served in the Continental Army from 1780 to 1783, ending as a sergeant at age 19. He received some schooling after the war and later became a captain in the new American Legion under the famous Revolutionary War hero, Major General “Mad” Anthony Wayne, during the war against western Indian nations. There, he faced some controversy and a court-martial for war profiteering and for releasing a prisoner from jail. He received a two-month “suspended commission.” 

In the quirky world of Federalist-era bureaucracy, he stayed in the army. He was appointed U.S. Consul to Tunis in 1797, making Eaton the main representative of the United States in the region. In 1804, he convinced the government to undertake a special operation to bring Yusuf’s brother, Hamet, into the conflict. The plan was approved, and Eaton led a small expeditionary force to Alexandria, where they joined up with Hamet and his ragtag mercenary army. With Marines and a few sailors as the core, they marched west to Derna and, after a fierce fight, captured the city. However, Hamet’s unreliability and peace overtures ended further efforts. Eaton returned to America, celebrated but bitter.

                                                                        William Eaton

Pressley O’Bannon

Arguably the fiercest warrior of the war (and the U.S. Navy had many of these) was a United States Marine officer, Lieutenant Presley O’Bannon. A native of Virginia and son of a Revolutionary War officer, O’Bannon joined the Marines in 1801 as a 2nd Lieutenant and was promoted to 1st Lieutenant the following year. He held various commands both aboard ship and on land, and during the Derna operation, commanded a squad of 8 marines and an ensign. 

O’Bannon’s bravery and daring were evident on April 27, 1804, at Derna. He led marines, some Greek mercenaries, and a few artillery gunners in a fierce charge through a hail of enemy musket fire. Ignoring the flying lead around him, he seized an enemy battery and raised the American flag on the city’s walls. He then turned the captured cannons on the enemy. After two hours of close combat, the fortress fell. This was the first time the stars and stripes flew over a fortress in the Old World during a time of war. 

O’Bannon was awarded a jeweled Mameluke scimitar for his bravery, and upon returning to Virginia, his home state, he was given a commemorative one as well. To this day, Marine officers wear a similar sword. After the war, he resigned his commission and moved west with his family, settling in Kentucky’s bluegrass region. An interesting Revolutionary connection: Legendary O’Bannon married the granddaughter of the ultimate Revolutionary War badass – the famed rifleman and General Daniel Morgan of Winchester, Virginia.

                                                        1st Lieutenant Presley O'Bannon

Tobias Lear

Another intriguing link to the Revolutionary War was Tobias Lear. The New Hampshire native did not serve in the war but attended Harvard from 1779 to 1783. Lear was an ambitious yet capable individual who moved from tutoring Martha Washington’s grandchildren to becoming George Washington’s secretary and trusted aide. He was visiting Mount Vernon when Washington died. 

Lear later earned the favor of President Thomas Jefferson, who, in 1801, appointed him as Consul-General to the North African coast. On June 4, 1805, Lear negotiated a "Treaty of Peace and Amity" with Yusuf. This was a difficult pill for many Americans to swallow. Lear arranged a ransom of $60,000 (about $1,024,400 today) for the release of sailors from the USS Philadelphia and several American merchant ships. Ironically, the Philadelphia was supposed to be the ship transporting him to the region, but a delay caused by his marriage plans (to a Washington/Custis girl) led him to sail on the Enterprise. 

                                                                            Tobias Lear

The Fighting Judge

 The Fighting Judge

If you drive up I-79 from Pittsburgh to Erie, Pennsylvania, the third-to-last exit is for a town named McKean, a small borough with about 300 residents. After many trips through the area, I decided to find out who this unassuming town was named after. A quick search led me into the world of an early patriot and founder who helped shape two states, a nation, and even a system of law. And he was not afraid of some combat along the way.

Son of a Tavernkeeper

Thomas McKean was born about twenty miles west of Wilmington, Delaware, in New London, Pennsylvania, on March 19, 1734. This connection is significant because McKean’s future was deeply linked to both Pennsylvania and the future state of Delaware, then known as the lower counties of the Keystone State. His parents were William McKean, a tavern keeper, and Letitia Finney. They had immigrated to Pennsylvania from Ballymoney, County Antrim, Ireland, when they were young, making McKean another first-generation patriot son of Ireland.

                                                    McKean's youth probably saw him

                                                    working in one of his father's taverns

    

Reading the Law

The younger McKean did not become a tavernkeeper. Instead, he received an excellent education, starting at the New London Academy and later in New Castle, Delaware, where he studied law under David Finney, a cousin. His “dual-jurisdiction” career began when he was admitted to the bar in 1755 in both The Lower Counties (Delaware) and Pennsylvania. A year later, he was appointed deputy attorney general for Sussex County. Political life quickly intertwined with law, and McKean served several terms in the General Assembly of the Lower Counties during the 1760s and 1770s, including a stint as Speaker. His intellectual credentials were confirmed when, in 1768, the talented jurist was elected to the American Philosophical Society. Not to remain idle, he also served as a judge of the Court of Common Pleas, and in 1771, he was appointed Customs Collector in New Castle. His impressive resume and the path to rebellion had not yet reached their peak. But tensions were rising.

                                                                Colonial Courthouse

The Lower Counties Splinter

Politically, the Lower Counties were divided into an Anglican pro-British faction, the Court Party, and a Scots-Irish patriot faction, the Country Party. Most counties supported the Court Party. New Castle was Scots-Irish and patriotic, and McKean soon became its leader. He first gained political recognition outside of Delaware when he represented the Lower Counties at the Stamp Act Congress of 1765, helped draft the petition to Parliament, and publicly called out the opposition, Timothy Ruggles, almost leading to a duel.

                                                          The Stamp Act Congress met at 

                                                                   Federal Hall in NYC

Revolutionary Politico

When the First Continental Congress was convened in 1774, McKean, along with Caesar Rodney and George Read, represented Delaware. He returned in the same capacity for the Second Continental Congress in 1775 and 1776. It was during the latter that he passionately advocated for independence. When he and Read split the Delaware vote, Caesar Rodney was not present. McKean called for Rodney’s return, and the famous midnight ride of Caesar Rodney led to Delaware voting 2-1 in favor of independence. The Declaration was then approved.

     Caesar Rodney's all-night ride 

would usher independence

Following the Drum

The ink was not dry on the Declaration when McKean suddenly left Philadelphia to take command as colonel of the Fourth Battalion of the Pennsylvania Associators, a militia unit. The battalion participated in the intense campaign to defend New York City in the summer and fall of 1776. It was later assigned to defend Perth Amboy, New Jersey. Due to his active military service, McKean missed signing the Declaration of Independence on August 2, 1776, and his signature was not on the printed copy that was authenticated on January 17, 1777. However, he signed the “death warrant” sometime afterward, and some believe he was the “last signer.” 

                                                McKean commanded one of the famed 

                                                                Associator Battalions

Wartime Politico

 Curiously, the Delaware Assembly did not elect either Rodney or McKean to Congress in October 1776. The firebrands had made some enemies, and many remained hesitant about full independence. However, the British victory at Brandywine in September 1777 came too close to home for comfort, prompting the election of both men in October. Despite relentless pursuit by the British and Loyalists, McKean continued to serve in Congress for the rest of the war. He helped draft the Articles of Confederation and was elected President of the Confederation Congress, serving from July through November 1781.

McKean was active in national as well as

PA & DE politics

First Son of Delaware

McKean was active in Lower County politics throughout the period leading up to the war and beyond. He frequently participated at both the national and local levels. He led the effort to make the Lower Counties a separate state, and in August 1776, the assembly selected him to attend a convention dedicated to drafting a new state constitution. 

McKean left his command and rode to Dover, Delaware, like a man possessed, and in one night, created the first draft of a Delaware Constitution, which the assembly accepted in September. This was the first state constitution drafted after the Declaration of Independence. He remained involved in the Delaware Assembly throughout the mid and late 1770s, even as he served in Congress. The British occupied Philadelphia and controlled the Delaware River from October 1777 through June 1778. During this time, both he and his family were at risk of capture by the British, and he had to change his residence about five times. 

                                                            British-occupied Philadelphia

Keystone Judge

While still active in Delaware politics, McKean faced the unusual situation of being appointed a judge in Pennsylvania, serving as Chief Justice from 1777 until 1799. McKean was a leading advocate for a judiciary with the power to overturn a state law if it was deemed unconstitutional. He was a very assertive jurist and established judicial review—the power of a court to strike down laws—before John Marshall established it for the US Supreme Court. His influential 22 years on the bench set precedents adopted by all the state courts nationwide.

                                                    McKean set precedents in jurisprudence

                                                                     before John Marshal

During this time, he served on the Pennsylvania convention, helping to ratify the new U.S. Constitution. Interestingly, since he helped draft the Articles of Confederation, which were later overturned. At the Pennsylvania State Constitutional Convention of 1789-90, he argued for a strong executive and supported the Federalists until 1796, when he became a vocal Democratic-Republican. He was unhappy with Federalist policies. As the Supreme Court justice of Pennsylvania, he supported suppressing the Whiskey Rebellion.

                                                        The Whiskey Rebellion posed legal 

                                                                as well as security issues

Chief Executive

McKean’s career on the bench ended when he was elected Governor of Pennsylvania in 1799. During his first term, he entered office as a partisan zealot, removing Federalists from their positions—the spoils system. By his third term, he had fallen out with his party and allied with the Federalists to fend off a challenge from a fellow Republican. He then replaced the republican officeholders with Federalists. McKean’s combative nature, his support for a strong state executive, and his willingness to turn against his opposition led the Pennsylvania House of Representatives to impeach him in 1807, but he remained in office until his term ended.

                                            Lancaster was the capital of Pennsylvania during 

                                                           McKean's tenure as governor

The Man

McKean was over six feet tall. He dressed stylishly in a cocked hat and a gold-knobbed cane. He had a quick temper, a thin face with a hawk-like nose and fiery eyes. He could be aloof and antagonistic, and by all accounts, he was a solitary man. He only socialized on public occasions. But he was undeniably brilliant and tireless.

                                                    McKean as Governor of Pennsylvania

In his correspondence, the not-so-liked himself, John Adams, paid him tribute by describing McKean as “one of the three men in the Continental Congress who appeared to me to see more clearly to the end of the business than any others in the body.”

The Family Man

The brilliant, active, but often acerbic McKean did find time for a family life. He married Mary Borden in 1763 and had six children with her: Joseph, Robert, Elizabeth, Letitia, Mary, and Anne. Mary died in 1773, and a year later, McKean married Sarah Armitage. He established his new household in Philadelphia, and they had four children: Sarah, Thomas, Sophia, and Maria. McKean and both of his wives were members of the Presbyterian Church. 

                                                                Sarah Armitage McKean

Retirement and Legacy

He spent his retirement in Philadelphia, writing, discussing political issues, and enjoying the wealth he had earned through investments and real estate. In 1790, he co-published "Commentaries on the Constitution of the United States." McKean was a founding member of the controversial (too aristocratic) Society of the Cincinnati in 1785 and even served as its vice-president. He received many honors: an LLD from Princeton in 1781, from Dartmouth in 1782, and from the University of Pennsylvania in 1785. When a second war with Britain threatened in 1812, the man in his eighties, McKean, led a group of Philadelphia citizens to organize a strong defense during the War of 1812.

                                                            McKean with son Thomas

McKean died in Philadelphia and was buried in the First Presbyterian Church Cemetery there. In 1843, his body was moved to Laurel Hill Cemetery. McKean was a dedicated lawyer who worked tirelessly, often juggling multiple tasks, for his community, his state(s), and his country—both in war and peace. This son of Irish immigrants set a precedent for the future laws and governance of the United States and all the states that would join the union. 

                                                        The McKean Grave at Laurel Hill