Henry Knox: The Boston Street Punk Who Rose to Become Washington’s Most Trusted General

Charles Willson Peale, Public domain, via Wikimedia Commons

In his early teens, Henry Knox was a big Scots-Irish bruiser and the most formidable member of Boston’s South End gang. Every 5th of November, these gangs celebrated the evening of Guy Fawkes Day with “Pope’s Night.” The South End gang and the North End gang would create these outrageous effigies of the Pope, the devil, and other adornments on carts. When the two gangs met at Mill Creek near Union Street, a fight would commence using brickbats, fists, feet, and whatever came to hand. The winner would seize their opponent’s cart and destroy it in a huge bonfire. On one such occasion, a wheel fell off the South End’s cart. The mighty Henry shouldered the axle, bringing it into the rendezvous, and both sides cheered. Neither cart was destroyed that night.

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Henry had not begun life at this end of the lower social scale. His father had been a prominent businessman, but his businesses failed, and in an attempt to avoid creditors, he fled to St. Eustatius in the West Indies, where he died a few years later. Henry’s mother was forced to pull him out of Boston Latin at the age of 9 and apprentice him. Fortunately for him, and for us, he was apprenticed to the Wharton & Bowes bookstore, where Nicholas Bowes took him under his wing, taught him the business, and encouraged him to borrow books on whatever subjects caught his interest. That turned out to be the military sciences, especially artillery and the design of fortifications. When he was promoted to an actual employee, his standing in the rigid social status of Boston improved. He would no longer participate in the South End gang activities, though he remained an advisor.

He joined a Boston artillery militia unit and applied what he had learned from books - how to build fortifications, how to transport heavy artillery, and most importantly, how to fire a cannon. He studied proper placement, trajectory, muzzle velocity, direct versus indirect fire, etc. When the “shot heard ‘round the world” had been fired in April of 1775, he offered his services to the militia that subsequently surrounded Boston. He was then employed to design fortifications, especially near the only land bridge to Boston, near Roxbury. 

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When Washington arrived to take command of the fledgling Continental Army, he took notice of those fortifications and the young man who had designed them. He very much liked what he saw in both and lobbied for a commission for Henry. When Washington told him that he was given command of the artillery, a bit of the “wise guy” from his youth surfaced, as he asked, just where was this artillery? That was the rub. There wasn’t much of any. But there WAS some, about 300 miles away at the recently captured Fort Ticonderoga. It was now November. Knox proposed to go get those cannons, in the dead of winter, and bring them back to their camp at Cambridge. Washington’s inner circle thought the scheme was madness, but Washington overruled them.

But he did it. He dragged 78 heavy guns, some of them 12- and 18-pounders weighing 5,000 pounds apiece, from upstate New York, across frozen ponds and rivers, over the Berkshire mountains, mostly by skidder sleds pulled by oxen. He finally arrived in Cambridge on January 24, 1775, with the artillery a couple of days behind him.

Some of those guns bore the insignia Ultima Ratio Regis: “ultimate argument of kings.” Ironic that they would soon be employed to return the “argument” against the king. In early March of 1776, the Continental Army, employing the “Yankee ingenuity” of Knox and others, muffled the wheels of wagons and lined the causeway with screwed hay to hide the sight and sound of the guns being slipped up to Dorchester Heights overlooking the town and the harbor, protected by portable fascines placed upon the frozen ground overnight. The British were forced to evacuate Boston.

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From that point on, Knox seldom left Washington’s side and was at every major battle. He engineered the crossing of the Delaware in the surprise attack on Trenton and the placement of the guns there. In the end, he commanded the artillery that slowly closed in on Cornwallis at Yorktown. Upon the ratification of the Constitution and the election of Washington as president, he became this nation’s first Secretary of War.

For a glimpse of some of his teen years and an epilogue on Dorchester Heights, including Knox’s eye-witness testimony in the Boston Massacre trials, there is our And Justice For All, Even Redcoats. Henry Knox is a main character.

Henry Knox’s story is uniquely American. He shares with later Americans such as Lincoln and Grant, and I daresay JD Vance today, a background where prospects seemed dim, but were overcome by talent, perseverance, and an attitude of “just get it done.” 

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