Contributor Question: Best Strategic Defeat?

Critical Thinking

March 13, 2019
by Editors Also by this Author


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This month, we asked our contributors to consider the many changes of fortune that occurred over the tumultuous four decades that transformed thirteen British colonies into the nascent United States:

What was the best strategic defeat, whether political or military, of the American Revolution and the founding era (roughly 1765 thru 1805)? That is, what defeat actually put the loser at an advantage, whether by design or by accident?

The remarkably diverse responses showcase the complexity of the era.

Gabriel Neville
Sinclair’s Defeat in 1791 was the highest casualty American loss in any battle until Shiloh in 1862. It was the last of a long string of strategically indecisive forays against the Ohio Indians. Andrew Lewis, Edward Hand, William Crawford, and Josiah Harmar are among those who led previous expeditions into the Ohio Country. Some, like Lewis, won a battle. Others, like Crawford, met gruesome deaths. These were typically militia campaigns that made no effort to hold territory. Arthur St. Clair’s army included both of the new nation’s regiments of full-time soldiers, levies on six-month enlistments, and militia. Squabbling, desertion, and delays led to a grisly end. The shocking loss, however,  motivated Congress to empower Washington to send a large, well-trained army under Anthony Wayne that seized and held the Northwest Territory in 1794. This initiated the robust national expansion that eventually went on to California and beyond.

Tom Shachtman
Thomas Jefferson’s narrow defeat by John Adams in the presidential election of 1796 proved to be an unexpected strategic boon to Jefferson, on several counts. First, he avoided the inevitable difficulties attendant on having to follow in George Washington’s gigantic footsteps as president—difficulties that severely hampered Adams.  Second, because Jefferson was not the president in 1797-1800, and therefore was not pledged to carry out policies with which he disagreed, he was better able to form and lead a coherent opposition party to that of the Federalists. Third, by 1800, changes in the electorate, which Jefferson had predicted and counted on, provided large majorities in the House and Senate for his party, helping him to govern and to assure that his basic policies would remain in effect for the next quarter-century.

Norma Desmarais
The battle of Bunker Hill was probably the greatest Pyrrhic victory of the war. The British held the ground at the end of the day (the criterion for a victory) but they suffered tremendous casualties—almost half of the force engaged and two and a half times more than the rebels. Its strategic effect was practically nil since the two armies remained in virtually the same positions they held before. However, it had great consequences. It showed that a force of farmers and townsmen, fresh from the fields and shops, with hardly a semblance of orthodox military organization, could fight on equal terms with a professional British Army. This astonishing feat had a sobering effect on the British as it taught them that rebel resistance would not be overcome easily.

Steven M. Baule
One of the defeats with the greatest impact was the British loss of remote Vincennes to George Rogers Clarke. Had Henry Hamilton and the British retained control of the Wasbash River Valley as well as Detroit and Mackinaw, they would have had a much stronger claim to the Ohio Valley (or at least the northern portion) while negotiating a treaty and the Mississippi and Ohio River Valleys may have remained in British hands. Had that happened, two decades later, there would have been no reason to try to buy New Orleans and much of the western US may have remained in the possession of France, Spain, and Great Britain. What if Chicago and Detroit were Canadian cities? As it was, British troops didn’t leave those posts until 1796 when Detroit and Mackinaw were finally abandoned. The British retook both posts in the initial moves of the War of 1812, but that is another story.

Robert Scott Davis
The great disastrous victory of the American Revolution was Guilford Courthouse of which one British officer proclaimed that another such British victory and the King’s army will cease to exist. It was responsible for Cornwallis’s later surrender at Yorktown, which ties all of the American Revolution, militarily together.

Eric Sterner
The Battle of Guilford Courthouse leaps to mind in considering Pyrrhic victories that hurt the winner more than the loser. Although Lieutenant General Charles Cornwallis “beat” Major General Nathanael Greene in North Carolina, his losses were such that he had to quit chasing the Continental Army through the Carolinas and turned toward the sea, where he might find reinforcements and craft new strategic opportunities. The British Army’s move freed Greene and his modest army to liberate the Carolinas and Georgia while Cornwallis eventually marched toward his destiny at Yorktown.

Michael J. F. Sheehan
One strategic “defeat” I might say put the “loser” at an advantage would be Hamilton and the famous dinner with Jefferson and Madison. Hamilton “lost” the City of New York as the Federal Capitol, yet in reality won support for his financial plans, while in reality, the banking and financial engines that would eventually move to the new Federal District remained for the time being in New York.

Edna Gabler
By design, two founders gained advantage through a strategic loss. On June 20, 1790, Jefferson hosted a dinner attended by Federalist Secretary of the Treasury Alexander Hamilton and Virginia Republican Representative James Madison. The three met to discuss an issue Congress had been grappling with for months.  Hamilton wanted the Federal Government to assume the states’ Revolutionary War debt, which he believed was necessary to establish the credit of the United States. Most northern states supported assumption because their debts were largely unpaid, while the southern states, having already paid off a large amount of their debt, opposed it.  In addition, they felt that by doing this the Executive branch gained too much power.  At the same time, Congress had been debating a permanent site for the capital. Madison wanted the capital located in the South, while Hamilton did not. At the timely dinner, a compromise was struck.  Madison agreed not to block assumption of state debt and to encourage enough southern states to support it.  In exchange, it was agreed that the capital would be located on the Potomac, after a ten-year temporary move to Philadelphia.  Thus a strategic loss for both Madison and Hamilton gave each an advantage they sought.

John L. Smith
The most advantageous strategic defeat of the Revolutionary War was the ill-fated American invasion of Canada 1775-1776. Although a failure in so many ways, the entire campaign which included the disastrous winter storm attack on Quebec City and the battle of Valcour Island, ended up buying time for the new Continental Army to get its act together. The year’s pause served as a delaying tactic (quite unintentionally) allowing American soldiers, supplies, logistics and leadership to coalesce into the force which defeated Gen. Burgoyne in his reverse invasion in late 1776. This while Gen. Carleton’s delayed British-Canadian troops had to halt their counter-attack at the Canadian border because of the onset of winter. An additional side benefit of the American invasion was that of forcing Great Britain to siphon off a large portion of its manpower, both British and Hessian, and redirecting it toward Canada rather than to the American colonies.

James Kirby Martin
A key patriot strategic goal in 1775 was to bring Quebec Province into the rebellion while inhibiting any British force form invading the colonies from Canada.  The British responded to the rebel invasion by sending thousands of troops to Quebec in 1776.  They drove the patriots back to New York, which fed their strategy of ending the war by cutting New England off from the rest of the colonies.  In turn, ongoing American resistance in the northern theater finally resulted in the defeat and capture of John Burgoyne’s army in October 1777. This British disaster spurred the French on to recognize American independence and openly provide vital support in arms, troops, and naval forces.  As such, the invasion of Canada, at first an embarrassing loss for the patriots, precipitated a chain of events in the North that  cost the British dearly–and perhaps ended any chance they had of actually winning the war.  From a strategic and operational perspective, the initial losers thus became the big winners and the initial winners became much bigger losers–an ironic outcome indeed.

Gene Procknow
The most fortuitous strategic defeat was the Rebel’s New Year’s Eve 1775 failed assault on the Royal garrison in Quebec City. If the Rebels had captured the city, an overwhelming British army/navy counterattack the next spring could have surrounded and forced a complete surrender of the Continental Army in Canada. Throughout the war, the British conquered significant port cities, and even the fabled walls of Quebec could not have withstood their siege guns and naval forces. Coupled with the simultaneous loss of New York City, the humiliating surrender of an entire Continental Army in Quebec might have been a fatal blow to the nascent armed rebellion. However, with the New Year’s Eve defeat, Rebel forces in Canada escaped to the more defensible Champlain/Hudson valleys, albeit with significant losses. The strategic retreat led to playing “interior defense” and negating British naval superiority. In 1777, Rebel forces coaxed invading British General John Burgoyne into the vast wilderness of New York State and to his eventual encirclement and surrender at Saratoga, the turning point in the Revolutionary War.

Rand Mirante
My candidate for “best strategic defeat”—and I suspect I won’t be alone in suggesting this one—would be the Battle of Valcour Bay, in which Benedict Arnold famously sacrificed his makeshift, outgunned “squadron” (and suffered criticism in some quarters for so doing), with the result being the blunting of General Carleton’s move southwards in October 1776. Arnold lost most of his naval force—sunk, captured, grounded, or destroyed—on Lake Champlain, but he bought a precious year for the defense of the Hudson, and he accomplished it in the face of a much superior, very ably commanded enemy.

Art Cohn
Many historians view the American naval defeat on Lake Champlain at the Battle of Valcour Island, October 11-13, 1776 as pivotal to the American victory at Saratoga one year later. The fifteen-vessel fleet under the command of General Benedict Arnold, by its very presence, forced a powerful British invasion force to first halt to create a fleet powerful enough to gain control of the strategic waterway. The linkage between the failed American fleet action in 1776 and the stage it set for American victory at Battle of Saratoga were perhaps best characterized by naval historian Alfred Thayer Mahan who wrote, “The Little Navy on Lake Champlain was wiped out, but never had any force, large or small, lived to better purpose or died more gloriously. That the Americans were strong enough to impose a capitulation of the British Army at Saratoga was due to the invaluable year of delay secured by their little Navy on Lake Champlain.” The legacy of that fleet action still provides us with tangible connections to the events that helped shape the nation.

Roger Smith
I believe that Spain’s victory at Pensacola gave them a false sense of superiority at the 1783 Treaty of Paris. This victory made them cocky enough to ask for Gibraltar at the peace talks, which they had twice-failed to take during the war. The end result of their inflated confidence was to get back West Florida, which they already had, and East Florida, which Britain no longer wanted.

Will Monk
Alexander Hamilton literally lost everything in his duel with Aaron Burr, but he has been lauded ever since (towns and counties named after him, the ten dollar bill, a Broadway show, dozens of books) while people in Burr County are still waiting for their man to be put on money that you can use to buy tickets to “AARON! The Musical.”

Gina Dimuro
I would argue that despite the alarmingly high casualties, the defeat of the Continental Army at the Battle of Brooklyn in 1776 was vital to their final victory. The battle only proved to the British that victory would be as easy as they had hoped. Rather than give immediate chase, they pursued Washington at a leisurely pace. This delay turned out to be a fatal mistake. The Americans made a miraculous escape and lived to fight another day. They would eventually regroup and, at Valley Forge, achiever the training they so desperately needed to stand against, and ultimately defeat, the British. Although New York was of tremendous strategic importance, its location between two rivers would have made it impossible to defend against the might of the British Navy. Had Washington held the city early on instead of escaped, his whole army could easy have been wiped out with one blow.

Ennis Duling
The Retreat from Ticonderoga and Mount Independence. On the night of July 5-6, 1777, nearly surrounded by the army under John Burgoyne, the Americans on Lake Champlain made a hasty retreat. Washington wrote, “The evacuation of Ticonderoga and Mount Independence is an event of chagrin and surprise not apprehended nor within the compass of my reasoning.” General Arthur St. Clair was widely condemned, and Congress ordered him court martialed. Now overconfident, Burgoyne marched south away from his supplies and toward a growing American army. After the surrender at Saratoga, Jeduthan Baldwin, who had been the engineer at the forts, wrote to St. Clair, “The people in general have altered their sentiments with respect to the evacuation of Ticonderoga. The officers, and all who I now hear speak about it, say a better plan could not have been adopted, and nothing but leaving that place could have given us the success.”

Kevin Diestelow
Although there are several readily apparent answers that come to mind (such as Bunker Hill), one can make a strong argument that “losing” the Battle of Yorktown put Britain in a strong position for success in the nineteenth century. Despite the battle signaling British defeat in the mainland theater, it allowed the British Army and Navy to more fully concentrate on more consequential theaters including the Caribbean, Gibraltar, and India. Growing the empire in these locations is what fueled Britain’s dominance both during and after the Napoleonic War. Continuing the war in mainland North America would have only further drained Britain’s resources. At Yorktown, the Empire cut its losses and turned to more strategic locations, heralding future growth.

Jim Piecuch
General William Howe’s victory at Brandywine and subsequent occupation of Philadelphia was the best strategic defeat the Americans could have imagined. First, Howe’s “triumphs” came so late in the campaigning season that he had little time to press his advantage, had he chosen to do so. Second, the focus on Philadelphia distracted Howe from Burgoyne’s campaign, put Howe’s army out of supporting distance, and allowed Washington to reinforce the New York army. Finally, the British had to evacuate Philadelphia in June 1778, leaving them with nothing to show for their victory while Washington’s army emerged from Valley Forge, intact better trained.

Richard J. Werther
I’ll take some liberties with the word “defeat” and term the failure of the Articles of Confederation a political defeat. The Founders leveraged this failure to replace the Articles with the Constitution. The Constitution is a document that has endured for over 200 years and brought us a nation of great strength and prosperity. Surely it had its flaws for which we have paid a steep price, most egregiously its failure to resolve the issue of slavery. Likely many of the founders would be surprised that their handiwork remains largely intact today, despite the stresses that are showing. Anti-Federalists might be saying “I told you so,” complaining that despotism from across the Atlantic has been replaced by despotism from a massive federal government at home. But all things considered, it’s hard to think of where we’d be without the “Miracle at Philadelphia.”

Geoff Smock
In 1786, nationalists within the Confederation Congress sought to pass a series of amendments that would have empowered the beleaguered and bankrupt national government to independently raise revenue, primarily through imposts. These amendments had near unanimous support—unfortunately they needed complete unanimity under the requirements of the Articles of Confederation to pass (Rhode Island was known as “Rogue Island” for a reason). This crushing defeat sent nationalists such as Madison and Hamilton into despondency. But it also gave them the sharpest arrow in their quiver yet to argue that the Articles were completely unworkable, and that a new plan of government was needed.

Jeff Dacus
The Race to the Dan in January of 1781 was a strategic defeat for Nathanael Greene. Pursued by Lord Cornwallis, Greene was forced to leave the Carolinas completely clear of Continental forces. In pursuing the Continental forces, Cornwallis was forced to burn his baggage and put his troops through an exhausting campaign. When Greene returned to the offensive in May, he suffered another tactical defeat at Guilford Court House but Cornwallis’ army was worn down again. Ultimately Cornwallis was forced to leave the Carolinas and move into Virginia where he was surrounded at Yorktown.

Ray Raphael
In the late summer and early fall of 1774, people in every shire town (county seat) of Massachusetts cast off British rule. Many then pushed for “independency” and wanted to attack the British garrison in Boston, the Crown’s last outpost in the province. This frightened Samuel Adams, who was attending the Continental Congress in Philadelphia. To his allies back home, he pleaded for caution: “I beseech you to implore every Friend in Boston by every thing dear and sacred to Men of Sense and Virtue to avoid Blood and Tumult. They will have time enough to dye. Let them give the other Provinces opportunity to think and resolve. Rash Spirits that would by their Impetuosity involve us in unsurmountable Difficulties will be left to perish by themselves. Nothing can ruin us but our Violence.” At the Massachusetts Provincial Congress, moderates prevailed and radicals retreated. Massachusetts would prepare for war but not start one, and that worked out well. When Britain did attack at Lexington and Concord the following spring, militia were better prepared and other colonies willingly joined the fray. We think of Samuel Adams as a radical, but here he preached retrenchment, the optimum strategy for that moment.

J. L. Bell
Gen. George Washington’s repeated defeats in councils of war he called during the siege of 1775-76. He kept proposing plans to attack the British in Boston. Washington offered plans on September 8, October 18, and February 16. His most spectacular idea was a charge across the ice of the frozen Charles River. Every time, his generals voted him down. Finally Washington asked what the council suggested instead, and they convinced him to try Gen. Artemas Ward’s plan to fortify Dorchester Heights and thus threaten ships in Boston harbor, which finally drove the British away. Washington believed that the Continental Congress had sent him to Boston to defeat the British army, not just to wait for it to leave. He believed that by bringing on a battle he could inflict Bunker Hill-level casualties on the enemy, making the ministry in London rethink the war. And he believed that military glory came in battle. When the British troops finally sailed away in March 1776 without a fight, Washington expressed “disappointment” in a private letter. In fact, Washington’s defeats in council were the best thing that could have happened to him. His subordinates saved him from making a reckless attack on fortified positions that would have cost the Continental Army dearly and stalled the move toward independence. As frustrated as he was during the long siege, Washington had those months to learn how to administer his large army and coordinate with civil governments.


  • I think out of all this diversity of opinion comes a kind of unity. If any one of them had turned out differently, perhaps none of the others would have happened, or maybe would have somehow changed the outcome of the war.

  • On reading the responses to the “Contributor Question,” the inclusion of St. Claire’s Defeat mildly surprised me—I hadn’t thought that far ahead in time. I would like to add a bit to Mr. Neville’s comments: in addition to the units he mentioned, the force included artillery, teamsters, and, sadly, about 200 women and children. Most of those people never got away from the bloody slaughter.

    For anyone interested in an excellent account of the battle, read Colin Calloway’s “The Victory With No Name” published in 2015 by Oxford Univ. Press. The site of the battle is also an interesting visit with a combination local and state historic site and a friendly, pretty town, Fort Recovery, OH, that is proud of all of its heritage, not just St. Claire’s Defeat.

    1. This bit prompted me to re-read Colin Calloway’s book on St. Clair’s Defeat and, on page 5 is a paragraph that deals with the posed question:

      “The defeat added to the growing divisions that eventually led to the creation of the first political parties. It produced the first congressional investigation in American history and in the process saw the birth of the principle of executive privilege, as the Washington administration considered whether of not to withhold documents that implicated Secretary of War Knox and Secretary of the Treasury Alexander Hamilton in the contractor fraud that had left St. Clair’s troops ill fed and ill equipped. It increased the federal governments’ role in shaping western development and expanding the American republic. It changed how Americans viewed, raised, organized, and paid for their armies and how they fought their Wars. It increased the president’s power to raise troops. It provided the impetus for creating a new army and for establishing that army as ‘the federal government’s most visible agent of empire.'”

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