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He was only 19 in the summer of 1775 when he arrived at the Continental Army encampment overlooking Boston. Though Aaron Burr had excelled at the College of New Jersey (now Princeton University), where his father and grandfather had been president, fighting the British did not require  Latin or Greek, rhetoric or natural philosophy. No one thought this young, short, slender intellectual would make much of a soldier. But appearances can deceive.

Over the next four years, this son of privilege endured bitter winters in Canada and Valley Forge and bloody battles ranging from Quebec to Monmouth Court House. He commanded a regiment, then a brigade, as a 22-year-old lieutenant colonel.

Through it all, Burr won the admiration of those who knew him best: the men he led. Decades later, they remembered him as a stern but evenhanded disciplinarian, a bold and nimble tactician. “For discipline, order, and system,” one recalled, Burr’s regiment “was not surpassed by any.” Another called it “a model for the whole army.” Burr retained a martial air through the rest of his tumultuous life. As a United States senator, then as vice president to Thomas Jefferson, and finally as a defendant facing the gallows in a treason case, he was addressed as Colonel Burr. The title fit. He had earned it.

The heroic reports of the Battle of Bunker Hill propelled Burr to Boston in early August 1775. Though he carried a written endorsement from a member of Congress, Burr found little to do in George Washington’s army. The youth from New Jersey was all but invisible in the confusion of conjuring an army from a ragtag mass of volunteers.

Burr’s slight figure undermined his military ambitions. “Your constitution,” one family friend wrote him, “is very delicate, and not formed for the fatigues of the camp.” The letter ended ominously: “You will die; I know you will die in the undertaking.”

Though Burr was soon bedridden with fever, his fighting spirit burned brightly. He learned that Benedict Arnold would lead a force into Canada through the backwoods of Maine, then rendezvous with another contingent that would invade through the Champlain and St. Lawrence Valleys. Burr rose from his sickbed and walked 60 miles to join Arnold at Newburyport.

The 350-mile march from the mouth of the Kennebec River in Maine to Quebec ended concerns about Aaron Burr’s delicacy. Half of Colonel Arnold’s men never reached Canada, turning back or succumbing to biting cold, swirling rivers, and relentless hunger. Burr thrived. When Arnold joined the other American force, he rewarded the young man’s pluck, commending him to Brigadier General Richard Montgomery for “great spirit and resolution on our fatiguing march.” Montgomery, an Irishman and British Army veteran, took a shine to the teenager and made him a captain on his personal staff.

The 675 invaders, relying on surprise and luck, hoped to seize Quebec’s hilltop fortress from a force about twice their number. Their nighttime assault stepped off in a snowstorm on New Year’s Eve. Surprise helped Arnold’s wing sweep into the lower town, but luck deserted Montgomery. Deep snowdrifts bogged down his column. When his force reached the town’s defenses, a single shot from a British cannon mortally wounded Montgomery. The attackers fled.

Through the years, the legend grew of the boy Burr at the gates of Quebec. Some said that after the initial fusillade he called for survivors to follow him in a renewed assault. Others claimed that he strained to shoulder his fallen general, a large man, and carry him to American lines. But his deeds did not need exaggeration. In the official battle report, penned by Arnold that same day, only Burr and two other officers were singled out—for having “behaved extremely well.”

At first, the defeat wore on Burr’s spirits. He was, he confided to his sister, “dirty, ragged, moneyless and friendless.” Yet an acquaintance in Philadelphia reported hearing tales of Burr’s daring: “The gentlemen of the Congress speak highly of you.” Another friend finagled an appointment for Burr to the staff of General Washington. Here, Burr might have thought, lay his route to military greatness.

But there was no chemistry between the reckless youth and the buttoned-up general. Joining Washington in the summer of 1776, Burr feared becoming a mere staff clerk. With a nudge from John Hancock, then president of Congress, he was appointed as aide to Washington’s second in command. Through the Battle of New York that summer, Burr found little chance of glory as the Americans first fought, then retreated from a powerful British army.

Burr’s only formal commission as an officer arrived a year later, in July 1777. Washington appointed him lieutenant colonel, second in command in the regiment raised by William Malcolm, a New York merchant. The new colonel’s ambition and resentment emerged in a reply to Washington. Pointing out that he would still be subordinate to men with less time in arms, Burr asked, “I beg to know…whether I may not expect to be restored to that rank of which I have been deprived?” Washington did not answer, leaving Malcolm and Burr to reach a unique arrangement. The senior officer retired to his country home and left Burr to command the regiment.

With the Malcolms, as the regiment was known, Burr was finally in charge. He relished the opportunity. In September, he organized a lightning attack at dawn against a larger British force near Hackensack, New Jersey, taking many prisoners and foiling a raid into his home state.

Yet Burr’s leadership shone as clearly in grinding garrison duty. During the bitter Valley Forge winter of 1777–1778, the Malcolms defended a lonely outpost where other units had faltered. Sharing his men’s hardships, Burr drilled discipline into his regiment.

Burr’s battlefield career had one more dramatic moment. In the broiling heat of late June 1778, he rode into the Battle of Monmouth Court House at the head of a full brigade that included the Malcolms. Stationed on the army’s left wing, Burr ordered his men to block a British flanking maneuver, only to be pulled up by a messenger from Washington. The general in chief, in a rage over Major General Charles Lee’s failure to press the attack earlier in the day, ordered Burr to stop. Caught between the army’s two top officers, Burr’s men were stranded in a ravine under hot fire. Burr’s horse dropped dead. A cannonball killed his second in command. At the end of a bloody but inconclusive day, Burr succumbed to heatstroke.

Disgruntled with Washington’s intervention, Burr sided with General Lee in the politicking that soon drove Lee from the army. Once more, Burr was on the wrong side of Washington, not a good place for an ambitious young officer.

By autumn 1778, Burr’s health had deteriorated. He took leave to recuperate. During a stay in Paramus, he met Theodosia Bartow Prevost, whose husband was a British officer in the West Indies. Burr rallied enough to note Mrs. Prevost’s intelligence and charm. In less than four years, following the death of her husband, he would marry her.

Burr returned to command in January 1779 in Westchester County, New York, a no man’s land where patriot and Tory forces terrorized residents while unaffiliated bandits made the most of a lawless situation. Finding that his own men were also plundering the locals, Burr despaired that his assignment was “truly an ominous commencement.”

His first priority, again, was discipline. Burr returned pilfered horses and livestock and turned his troops to their proper duties. A comrade recalled Burr’s tireless oversight of the army’s widespread outposts: “Seldom sleeping more than an hour at a time,” Burr visited each one “between midnight and two o’clock in the morning.” The men soon learned that their colonel was always keeping an eye on them.

Burr again melded his force into one acclaimed for its effectiveness, but he resolved to resign his commission after only a few months of such inglorious service. His health was still poor and he despaired of advancement in Washington’s army.

Burr also hoped to spend more time with Mrs. Prevost.

The army left a greater impression on Burr than he left on it. He neither achieved high command nor won great victories, but he would always see himself as a military figure.  He was a man of action, not one of ideas, and army life suited him. As one lifelong friend remembered after his death, “All his views and feelings were military.”

But after 1779 he never again donned a uniform. Twenty years later, having built a sterling reputation as a lawyer and after serving as New York’s attorney general and a U.S. senator, another national crisis drew Burr back to the military. As the United States careened toward war with France in the late 1790s, Burr sought high rank in the armed forces but once again collided with George Washington. Summoned from retirement to lead the revived army, Washington told President John Adams that Burr was “a brave and able officer” but questioned “whether he has not equal talents at intrigue.” One last time, Washington passed over Burr.

By 1805 Burr’s political career was foundering, victim to Jefferson’s enmity and the fallout from his legendary duel the year before with Alexander Hamilton. Burr’s thoughts turned to military matters. He agitated with state militia generals and America’s general in chief, James Wilkinson, for an invasion of the Spanish colonies of Florida and Mexico.

Burr ached to lead that invading army. He recruited hundreds of volunteers and built dozens of riverboats to carry them to New Orleans. When the expedition fell to ashes, Burr landed in a Richmond courtroom facing charges of treasonously inciting the secession of America’s western lands.

After winning an acquittal, Burr clung to his martial ambitions. He wandered Europe for four years, seeking support from Britain and France for an expedition to liberate Spain’s American colonies. With the right backing, he thought, he might yet conquer his way into history. By 1812, penniless and shivering in a Paris garret, Burr gave up the dream. He limped back to New York, where he soon knew only the combat of the courtroom, practicing law until his death in 1836.

DAVID O. STEWART, a lawyer in Washington, D.C., has written three works of history since 2007. His latest book, American Emperor: Aaron Burr’s Challenge to Jefferson’s America, was released in paperback in the fall of 2012.

Originally published in the Winter 2013 issue of Military History Quarterly. To subscribe, click here.