The Incredible American Generals that Defined their Eras

The Incredible American Generals that Defined their Eras

Khalid Elhassan - May 4, 2022

In the American Revolution, General George Washington served as commander in chief of the Continental Army, as well as the country’s chief spymaster. Desperate for intelligence about the enemy, Washington personally oversaw and monitored the development of spy networks, including one that became the most successful spy ring in America’s history. Below are thirty things about that and other lesser-known facts about American generals.

The Incredible American Generals that Defined their Eras
George Washington. Owlcation

30. The Country’s Chief General Was Chiefly Interested in the Enemy’s Activities in This City

In America’s War of Independence, George Washington served not only as the nascent country’s chief general, but also as its chief spymaster. Washington was well aware that the deck was stacked against the Patriots in their confrontation with the mighty British Empire. So he tried all he could to improve the odds, and the key to that was access to intelligence about the British. Good information about his enemy’s strengths, weaknesses, and intentions, was vital if Washington was to play his otherwise weak hand as well as possible. He was especially interested in British activities in New York City and its environs.

The Incredible American Generals that Defined their Eras
Washington’s troops evacuating New York City under the cover of darkness. Pinterest

Boston takes center stage in people’s minds when they think of the American Revolution. However, after the first few months of fighting, the British departed and Boston became a military backwater. The action then shifted to New York, which took center stage for the rest of the conflict. In the summer of 1776, ala The Empire Strikes Back, the British descended upon NYC and won the war’s biggest battle in Long Island on August 27th, 1776. Washington and the Continental Army had to hole up in Brooklyn, and it took a near-miracle for them to escape. New York became the main British base, and as seen below, Washington was desperate to find out as much as possible about what they were up to.

The Incredible American Generals that Defined their Eras
The execution of captured American spy Nathan Hale. History on This Day

29. America’s Chief General Also Doubled as its Chief Spymaster

After his defeat in New York, General George Washington directed that a “channel of information” be established in Long Island. The result was an amateurish affair without permanent agents on the ground. It came to grief when Nathan Hale, a young officer who volunteered to gather intelligence from behind British lines, was captured and executed as a spy. That convinced Washington that civilians would make better spies than soldiers. So in February, 1777, he directed a Nathaniel Sackett to spy on the British, and appointed a Major Benjamin Tallmadge, a New York native, as military liaison. The information gathered was often hit or miss, however, and a frustrated Washington eventually sacked Sackett.

The Incredible American Generals that Defined their Eras
Code used by the Culper Ring in correspondence with George Washington. Pinterest

Washington was frustrated with other intelligence efforts until August, 1778, when he accepted an offer by a Caleb Brewster of Connecticut to spy behind British lines. Within weeks, Brewster sent in accurate reports of British troops and ships. Washington ordered Tallmadge to build up on Brewster’s efforts, and personally oversaw the major’s efforts as he established the Americans’ first reliable intelligence pipeline in enemy territory. As seen here, Washington was hands-on throughout. He acted as his own spymaster, exchanged invisible ink letters with the spies, and gave them detailed instructions about the information he wanted them to gather. They delivered and handed Washington timely and vital information that contributed greatly to America’s ultimate victory.

The Incredible American Generals that Defined their Eras
For generations, General Abner Doubleday was credited with the invention of baseball. The Junkie

28. The General Who Was Credited With the Invention of Baseball

Abner Doubleday was a career US Army officer, who fired the first shot in defense of Fort Sumter at the start of the American Civil War. He rose to general rank in the Union Army, and played a pivotal role during the Battle of Gettysburg. On the civilian side of the ledger, he secured a patent on the San Francisco cable car railway that runs to this day. He is best known, however for his links to baseball, and he was credited for many years as having invented the game in the 1830s. As it turned out, the baseball story was a myth, but although he did not invent a national sport, Abner Doubleday still had a significant national impact.

The future general Doubleday was born in 1819 in New York, to a family of warriors. His father had fought in the War of 1812, his paternal grandfather fought in the Revolutionary War on the side of the Patriots, his maternal grandparent had been a messenger for George Washington, and at least one of his great grandparents had been a Minuteman. Doubleday was accepted into West Point in 1838, graduated four years later, and was commissioned as an artillery officer. Before the Civil War, he fought in the Mexican War, 1846 to 1848, and in the Seminole Wars, 1856 to 1858.

The Incredible American Generals that Defined their Eras
Abner Doubleday’s position on the first day of the Battle of Gettysburg. Wikimedia

27. The Man Who Fired the First Shot in Defense of the Union

In 1861, Abner Doubleday was second in command in the federal garrison at Fort Sumter when it was fired upon by Rebels to start off the Civil War. He personally aimed the first cannon that returned fire, and forever after credited himself with firing the war’s first shot in defense of the Union. After the Sumter garrison capitulated and vacated the fort, Doubleday served in the artillery of the Army of the Potomac. By the time of the Second Battle of Bull Run in 1862, he had risen to command of a brigade. Following the Union defeat in that battle, he took charge of his division after its commander was wounded, and led it as it covered the rest of the army’s retreat.

At the Battle of Antietam, the division commander was again wounded, and Doubleday again took charge, and led his men in fierce fighting in which he was wounded. By the time of the Battle of Gettysburg, Doubleday had been appointed to permanent command of his own division in the Army of the Potomac’s I Corps. It was the first Union corps to arrive at the field of battle. It reinforced a cavalry commander who had been fighting a delaying action west of Gettysburg, in order to buy Union forces enough time to reach and occupy a strong defensive position south of the town.

The Incredible American Generals that Defined their Eras
General Abner Doubleday. New York Times

26. The General Who Bought the Union Time for a Chance to Win the Battle of Gettysburg

On the first day of fighting at Gettysburg, I Corps’ commander, General John F. Reynolds, was killed, and General Abner Doubleday stepped into his shoes and took charge. Leading 9000 men, he fought off nearly twice as many Confederates for five hours. Doubleday’s command sustained horrific casualties before he was forced to retreat to defensive positions on the high ground south of Gettysburg. I Corps was effectively destroyed in that first day’s fighting, and shattered so badly that it would be decommissioned the following year, with its components sent off to reinforce other corps.

However, Doubleday had bought the rest of the Union army enough time to reach the field of battle, and secure the high ground for whose possession Doubleday had sacrificed his corps. The Battle of Gettysburg over the next few days boiled down to the Confederates vainly attacking the Union forces in an attempt to knock them off the heights that Doubleday had secured. The Rebels were beaten back each time, culminating in Picket’s Charge on the battle’s last day, before they admitted defeat and retreated back to Virginia.

The Incredible American Generals that Defined their Eras
Abner Doubleday’s tombstone in Arlington National Cemetery. US Army

25. No Good Deed Goes Unpunished

Without General Abner Doubleday’s ferocious stubbornness on the first day of Gettysburg, things could have gone differently in the Civil War’s greatest battle. The story could well have been one in which the Confederates were the ones to first secure and occupy the heights south of Gettysburg. The Army of the Potomac’s morale was none too high after humiliating defeats in the preceding months in the Battles of Fredericksburg and Chancellorsville. It was also under a newly appointed commander whom most did not know. It would have been forced to attack strong defensive positions situated on high ground, that were manned by an enemy brimming with confidence after a string of recent successes. Because no good deed goes unpunished, Doubleday was penalized rather than applauded.

General George Meade, the Army of the Potomac’s new commander, disliked Doubleday. He thus was inclined to believe false reports that I Corps under Doubleday, rather than saving the day, had broken and fled, causing the entire Union line to unravel. So Meade took I Corps from Doubleday, and sent him back to command his division. Doubleday fought well in charge of his division throughout the rest of the battle, and was wounded in the process. But he neither forgot nor forgave Meade’s injustice. After the war, Doubleday was stationed in San Francisco, where he secured a patent for the cable car railway that still runs there to this day. He retired from the US Army in 1873, became a New York lawyer, and wrote memoirs and histories of the Civil War. He died in 1893, and was buried in Arlington National Cemetery.

The Incredible American Generals that Defined their Eras
General Douglas MacArthur at the Inchon Landing. Smithsonian Magazine

24. A General Whose Brilliant Maneuver Turned the Tide of a Seemingly Lost War

When the Korean War broke out in 1950, the North Korean army got off to a good start. In seemingly no time, it routed the South Korean army and American forces in their path, en route to overrunning most of South Korea. Within a few months, all that was left in South Korean and American hands was a small sliver of territory around the port city of Pusan. Things seemed hopeless until American General Douglas MacArthur reversed the tide of the war with a brilliant maneuver.

He outflanked the North Koreans with an amphibious landing in September of 1950 at Inchon, near the South Korean capital city of Seoul. That placed American forces north of the North Korean army trying to take Pusan, and severed their main supply line. That sudden turning of the tables led to the collapse of the North Korean invasion, and a panicked retreat of the invaders that swiftly turned into a rout. MacArthur vigorously pursued the demoralized enemy northward up the Korean Peninsula.

The Incredible American Generals that Defined their Eras
Chinese forces cross the Yalu River into North Korea during the Korean War. Wikimedia

23. A Commander Who Snatched Defeat from the Jaws of Victory When he Ignored Warnings of a Looming Threat

As General Douglas MacArthur’s forces drew closer to the Chinese border, concerns grew about Beijing’s reaction if American forces reached China’s borders. Despite mounting evidence that China would directly intervene in the war if his forces approached the Sino-Korean border, MacArthur blithely dismissed all warnings, and insisted that the Chinese would do nothing. MacArthur turned out to be very, very, wrong. Soon after his forces reached the Yalu River, which marked the border with China, the Chinese began to pour across in the hundreds of thousands.

The Chinese arrival in North Korea went undetected, and in November of 1950, they struck. Their sudden eruption surprised MacArthur and caught him completely off guard. Within weeks, the American general’s gains had been lost, and his forces had been forced out of North Korea. MacArthur’s judgment and estimate of Chinese reaction had been proven catastrophically wrong. His forces had been chased back down the Korean Peninsula by the Chinese even faster than they had raced up the Peninsula in pursuit of the North Koreans.

The Incredible American Generals that Defined their Eras
President Harry S. Truman and General Douglas MacArthur. Modern War Institute

22. The General Who Wanted to Start WWIII to Salve His Bruised Ego

Humiliated by having been forced to hastily retreat down the Korean Peninsula, General Douglas MacArthur reacted with histrionics, and insisted that atomic bombs be dropped on China. His plan was to drop up to 50 atomic bombs in Manchuria on Chinese cities, military concentrations, and communication centers. The result, as he envisioned it, would be to seal off the Korean Peninsula from China by creating a radioactive belt across Manchuria, stretching from the Sea of Japan to the Yellow Sea. President Truman, whom MacArthur had confidently assured only weeks earlier that China would do nothing if his forces marched up to the Chinese border, balked.

The president declined to put his faith in yet more confident assurances from MacArthur, who now asserted that the Soviets would do nothing if the US dropped dozens of atomic bombs on their Chinese ally. So MacArthur turned prima donna, and publicly contradicted Truman’s position. He was ordered to clear any further statements on the subject with the State Department first. When MacArthur violated those orders, and again challenged Truman publicly on the use of atomic weapons in the Korean War, Truman finally had enough and fired him.

The Incredible American Generals that Defined their Eras
General George S. Patton. Europe Remembers

21. The Bad Side of a Great General

George S. Patton is America’s most famous fighting general of WWII. He led the US Seventh Army in North Africa and Sicily, and commanded the Third Army as it stormed through France, across Germany, and into Czechoslovakia. A man of contradictions, Patton was a hard-charging, profane, and often obnoxious figure. He also had a softer side, and liked to write poetry – although not very well. And then there was the crazy side, in which this great general convinced himself that he was some kind of eternal soldier, having been reincarnated numerous times over the millennia as a warrior. In short, Patton was a man of extremes. He also elicited extreme reactions: people loved or hated him. He gave the latter plenty to hate, as his wartime exploits were often marred by controversies stemming from his propensity to abuse his authority and those under his command.

The Incredible American Generals that Defined their Eras
George S. Patton in WWII. YouTube

One incident from 1943, in which he slapped sick soldiers, almost cost him his career. It was nothing compared to another incident in 1945, hurriedly swept under the rug, in which Patton got hundreds of his men killed, wounded, or captured, because of nepotism. General Patton’s best-known controversy occurred during the 1943 Sicilian Campaign. On a hospital visit, he came across a PTSD-suffering soldier who was also burning up with malarial fever. Seeing no visible wounds on the GI, Patton flew into a rage, accused the unfortunate man of cowardice, slapped him around, and threatened to shoot him. The great general repeated the disgraceful performance a few days later in another hospital and physically assaulted another PTSD-suffering soldier. When the scandal broke, it nearly got Patton cashiered from the US Army. Fortunately, General Dwight D. Eisenhower protected Patton and gave him a chance to command another army in France.

The Incredible American Generals that Defined their Eras
General George S. Patton. Wikimedia

20. Patton Squandered Hundreds of GIs Because of Nepotism

General Patton did not learn the lesson about abuse of power. In 1945, he had a worse, but lesser-known scandal, in which he got hundreds of GIs killed, wounded, or captured, for personal reasons. It happened in March 1945, when Patton ordered Task Force Baum, comprised of 314 men, 16 tanks, and dozens of other vehicles, to penetrate 50 miles behind German lines. Their mission: to liberate Hammelburg POW camp, which housed Patton’s son-in-law, John K. Waters. Task Force Baum’s raid ended catastrophically. All tanks and vehicles were lost, and of 314 participants, 32 were killed, and most of the rest were wounded or captured. Only 35 men made it back. The worst part of it was that the mission was totally unnecessary. Patton’s beloved son-in-law, for whom the great general had gotten the beloved sons, brothers, and fathers of many Americans killed or injured, had never been in any danger.

The Incredible American Generals that Defined their Eras
Units of the 14th Armored Division liberate a POW camp a few weeks after the Task Force Baum Fiasco. US National Archives

Hammelburg was liberated two weeks after the Task Force Baum fiasco. When Eisenhower found out, he was furious at Patton’s misuse of military personnel and assets for personal reasons, and reprimanded him. In light of his valuable services, however, Eisenhower declined to punish Patton beyond the reprimand. Shortly thereafter, a reporter got wind of the scandal. When the story first broke in a major publication on April 12th, 1945, it would have wrecked Patton under normal circumstances. However, FDR died that same day, and his demise eclipsed all other news. The scandal got little traction, and when Patton died a few months later, the affair was reduced to a mere historic footnote.

The Incredible American Generals that Defined their Eras
A copy of Special Orders No. 191, displayed at Crampton’s Gap, Maryland. Wikimedia

19. The Union’s Lowest Point

During the American Civil War, the autumn of 1862 might have been the lowest point for the federal government and for the Union’s cause. The year had started promisingly enough with a campaign that sought to capture Richmond. Things went well at first in what came to be known as the Peninsula Campaign, but a series of mistakes turned it into a fiasco. Then the Confederates under General Robert E. Lee dealt the federals a humiliating defeat at the Battle of Second Bull Run, and early in September, Lee’s Army of Northern Virginia invaded Maryland.

Things were looking bleak, with Britain and France about to recognize the Confederates’ independence, when the Union caught an unexpected break. On September 13th, as the Army of the Potomac hurried to catch up with Lee, Union Army Corporal Barton Mitchell arrived at a campsite recently vacated by the enemy. There, he found an envelope with three cigars wrapped in some paper. The papers turned out to be Special Orders No. 191, in which Lee had spelled out his army’s movements.

The Incredible American Generals that Defined their Eras
The Battle of Antietam. Pinterest

18. A Lucky Find for One General, an Unfortunate Loss for Another

Special Orders No. 191 were rocketed up the Army of the Potomac’s chain of command until they reached its chief, General George B. McClellan. He was pleasantly surprised to discover that Robert E. Lee’s army was spread out, and that fate had gifted him a golden opportunity to defeat his enemy’s scattered units one by one, before they could unite. Unfortunately, McClellan was not good at seizing golden opportunities, and Lee managed to concentrate his army in the nick of time.

The result was a major battle fought in the vicinity of Antietam Creek on September 17th, 1862. It was the bloodiest day in American history, with a combined tally of over 22,000 dead, wounded, and missing. McClellan had a chance to finish off Lee’s army but failed to do so. Nonetheless, the horrific casualties ended Lee’s Maryland Campaign, and forced him to withdraw to Virginia. The Confederates never came as close again to winning the war as they did that September of 1862.

The Incredible American Generals that Defined their Eras
General Curtis LeMay and President John F. Kennedy. Politico

17. The Cold War’s Most Dangerous Moment

During the Cuban Missile Crisis in 1962, the Pentagon urged President Kennedy to invade Cuba in order to remove Soviet nuclear missiles from the island. The Joint Chiefs of Staff unanimously agreed that a full-scale invasion was the only solution. They presented the president with two plans: Oplan 316 for a full invasion, and Oplan 312 for aerial strikes to take out the missiles, followed by an invasion if necessary. The hawks, led by Air Force General Curtis LeMay, had a clear preference for Oplan 316. They argued that there was no guarantee that airstrikes alone would take out all the missiles, or that one or more of the missiles would not be fired at the US.

The Incredible American Generals that Defined their Eras
Nikita Khrushchev and Fidel Castro. Defense Media Network

Planners expected 18,500 US casualties in the first ten days of the invasion, assuming no nuclear explosions. However, unbeknownst to planners, the Soviet forces in Cuba had tactical nuclear weapons. Worse, Soviet leader Nikita Khrushchev had preauthorized the Soviet commander in the island to use tactical nukes at his discretion if he deemed it necessary. As the crisis intensified, Khrushchev withdrew release authority and forbade their use without his express permission. However, whether the modified orders would have been followed, is debatable.

The Incredible American Generals that Defined their Eras
President John F. Kennedy, with General Curtis LeMay to his immediate right. Medium

16. The Combative General Who Wanted to Risk WWIII

In practice, tactical nukes were dispersed throughout Cuba to various Soviet units, under the physical control of officers as low down the chain of command as captains. Soviet forces had drilled in the use of those weapons as part of their defensive plan. In the heat of battle, the custodians of those weapons would have been under intense pressure as they were subjected to overwhelming US aerial strikes, naval bombardment, and ground attacks. It is not difficult to envision a desperate local commander in such a scenario, perhaps cut off from communications with higher authority, resorting to the tactical nukes at hand to save his command, or at least ensure that its demise did not come cheap.

The Incredible American Generals that Defined their Eras
Editorial cartoon from the days of the Cuban Missile Crisis. Encyclopedia Historia

The Red Army at the time, with victory in WWII only 17 years in its past, did not lack military pride or an ethos of defiance unto death. If the Soviets used nukes in Cuba, the US intended an overwhelming nuclear response. Things could easily have escalated from there to a full-blown nuclear exchange that would have devastated both countries and Europe, irradiated the Northern Hemisphere, and set humanity back centuries. Luckily, President Kennedy resisted the pressure from his generals and admirals, especially General Curtis LeMay. Instead, JFK relied on diplomacy, back channels, and blockade, to successfully defuse the crisis without triggering WWIII.

Read More: 19 Things About the Cuban Missile Crisis of 1962.

The Incredible American Generals that Defined their Eras
General Isaac Brock. Legislative Assembly of Ontario

15. The British Attack on Fort Detroit in the War of 1812

In the early days of the War of 1812, British General Isaac Brock marched on Fort Detroit. Under his command was a force of 1330 men, comprised of 330 Redcoats, 400 Canadian militia, and 600 Native Americans, supported by 3 light guns, 5 heavy guns, 2 mortars, and 2 warships. Brock’s target was garrisoned by an American force nearly twice the size of his own, comprised of 600 US Army regulars and nearly 2000 militia, sheltered within the protective walls of a fortress that had at least 36 cannons.

The garrison was commanded by an American Revolutionary War veteran and hero, General William Hull. Brock learned from captured messages that American morale was low, that the garrison was short of supplies, and that his enemies were terrified of his Native American allies. Emboldened by that information, Brock decided to immediately attack Detroit, and exploited the Americans’ fear of Indians. Brock arranged for a misleading letter to fall into American hands, that greatly exaggerated the number of his native allies from an actual 600 to a fanciful 5000.

The Incredible American Generals that Defined their Eras
General William Hull in Fort Detroit. Imgur

14. A General Who Fell for a Bluff

General Brock also tricked the Americans into believing that he had more regulars under his command than was the case, by dressing his Canadian militia in castoff British regimental uniforms. Outside Detroit, he had the same troops march in a loop over the same stretch within eyesight of the garrison. They would then duck out of sight, and return to march anew as if they were fresh reinforcements. Brock also ordered his troops to light five times as many fires at night than was the norm, in order to further convey an illusion of greater strength.

General Hull’s already low confidence collapsed at the prospect of facing a strong British army accompanied by 5,000 Natives. Brock sent a message demanding surrender, and informed Hull that he did not want to massacre the defenders, but that he would have little control over his Indian allies once fighting commenced. Hull, unwilling to sacrifice his men against hopeless odds, and fearing for the women in children inside the Fort, including his own daughter and grandchild, decided that resistance was futile. So he raised a white flag and asked Brock for three days to negotiate the terms of surrender.

Read too: Greatest Military Bluffs in History.

The Incredible American Generals that Defined their Eras
General William Hull, surrendering Fort Detroit. ThoughtCo

13. A Shameful Surrender

General Brock kept up the psychological pressure on General Hull, and gave the American garrison commander only three hours instead of the requested three days before he would attack. Hull caved in and surrendered his entire command of nearly 2500 men, three dozen cannons, 300 rifles, 2500 muskets, and the only American warship in the Upper Lakes. The British suffered only two men wounded. The surrender of Fort Detroit was a military disaster for the US, and derailed plans to invade and seize Canada early in the war, before the British had time to rush in reinforcements.

It also reinvigorated the Canadians, who had been pessimistic about the prospects of defending Canada from forcible annexation by the US. Additionally, it fired up Native Americans in the Northwest Territory to war against US outposts and settlers. An American invasion of Canada was attempted later on, but by then the British and loyal Canadians were better prepared and more confident and forced the invaders back across the border. As to General Hull, after his release from British captivity, he was tried, convicted, and sentenced to be shot. However, his life was spared out of consideration for his heroism decades earlier during the American War of Independence.

The Incredible American Generals that Defined their Eras
General George B. McClellan. Wikimedia

12. The Union General Who Came Close to Capturing Richmond in 1862

In March, 1862, Union General George B. McClellan outflanked the Confederate main army in Northern Virginia by landing 121,000 men on the Virginia Peninsula to the south, between the James and York rivers. The goal was to march up the Peninsula and capture Richmond before the Confederates had time to rush in reinforcements to protect their capital. Things went smoothly at first, as McClellan successfully disembarked with no difficulty, and began his march to Richmond. The only opposition between McClellan and Richmond were 12,000 Confederates at Yorktown, commanded by General John B. Magruder and outnumbered 10 to 1 by Union forces.

Magruder, aware that his small force stood no chance in a fight, and desperately needing to buy time until reinforcements arrived, set out to bamboozle McClellan into slowing down. Fortunately for the Confederates and unfortunately for the Union, Magruder was the right man in the right place at the right time. He was known before the war for his florid manner and proneness to theatrics and ostentatious displays. Now, he resorted to theatrics and display to put on a show and trick McClellan into believing that he faced far stronger opposition than was the case. He pulled it off.

The Incredible American Generals that Defined their Eras
General John B. Magruder. Calisphere

11. Elaborate Trickery to Halt a Much Stronger Enemy

General Magruder took advantage of the small Warwick River which separated him from the advancing federal forces. The Confederate commander set out to convince his Union opposite, General McClellan, that the river’s fourteen-mile length on the opposite bank was heavily fortified and strongly garrisoned. While the fortifications were real, Magruder lacked the men to occupy them in any strength that could have stopped McClellan had he attacked. Magruder directed his forces to create a din, with drumrolls and men cheering in the woods behind the lines, to fool their foes into believing there were far more Confederates in the vicinity than was the case.

He also employed the same column of men over and over. They would march within sight of the federals to take up positions on the defensive line, then slip away outside the Union observers’ line of sight, reassemble in column, and march back to the defense line to take up defensive positions once more. With such theatrics, Magruder convinced McClellan that the Confederate positions were too strong for a frontal attack. It was a task made easier by McClellan’s predisposition to take counsel of his fears and believe himself outnumbered.

The Incredible American Generals that Defined their Eras
The Warwick River line and the 1862 Siege of Yorktown. Wikimedia

10. Timidity Kept This General From Seizing Richmond and Winning the Civil War in 1862

On April 5th, 1862, General George B. McClellan ordered a halt on his side of the Warwick River, had his men dig in, and set out to conduct a siege. Unbeknownst to him, he could have simply bulled through, swatted Magruder aside, and seized Richmond as it was his for the taking. For a month, McClellan methodically prepared for a huge attack to break through Magruder’s “strong defenses”. He concentrated men, guns, and munitions for a massive bombardment scheduled for May 5th, 1862, followed by an overwhelming attack.

Having already bought his side a month to prepare for the defense of Richmond, Magruder slipped away on the night of May 3rd, and left behind empty trenches for the enemy to occupy. McClellan resumed his advance on Richmond, but by then the Confederates had concentrated sufficient forces to thwart him. McClellan was halted at the gates of Richmond, then pushed back to his starting point with furious attacks during the Seven Days Battles. The Peninsula Campaign thus came to an ignominious end.

The Incredible American Generals that Defined their Eras
Benedict Arnold. History Network

9. America’s Most Infamous Traitor Was Once a Brilliant General in America’s Cause

American Revolutionary War General Benedict Arnold (1741 – 1801) is the United States’ most infamous traitor. His name has become an epithet, synonymous with treason and betrayal. At one point, though, he had been a leading patriot in the fight against the British, and was perhaps the most capable combat leader on the rebels’ side. Then a combination of resentments over slights, coupled with financial distress, led him to sell out to the enemy. Before he turned traitor, Arnold had provided valuable service to the American side, and played a key role early in the war in the capture of Fort Ticonderoga. He then led an expedition through extremely rough terrain in an attempt to capture Quebec.

The Quebec Expedition failed in its ultimate aim, but General Arnold exhibited remarkable leadership in getting his men to the outskirts of Quebec. In 1776, an enterprising Arnold constructed a fleet from scratch at Lake Champlain, which he used to defeat a vastly superior British fleet. While lionized as a hero by the public, his successes, rash courage, and driving style aroused the jealousy and resentment of other officers, who backbit and schemed against Arnold. When Congress created five new major generals in 1777, Arnold was stung when he was bypassed in favor of some of his juniors. It took George Washington’s personal entreaties to prevent Arnold’s resignation.

The Incredible American Generals that Defined their Eras
Benedict Arnold’s wife, Peggy Shippen Arnold. History of American Women

8. A Turn to Treason

Benedict Arnold stuck around long enough to repel a British attack in Connecticut, and was finally promoted to major general. However, his seniority was not restored – another slight that would gnaw at him. He again sought to resign, but was again prevailed upon to remain. He performed brilliantly in halting the British advance into upstate New York in 1777, which culminated in the British surrender at Saratoga, where Arnold fought courageously and was severely injured. Crippled by his wounds, he was put in charge of Philadelphia, where he began to socialize with British loyalist families. He also took to extravagant living, which he financed with questionable dealings that led to a scandal. While in Philadelphia, he met and married a much younger woman of loyalist sympathies and spendthrift habits that soon put Arnold deep in debt.

The Incredible American Generals that Defined their Eras
A French map of West Point in 1780. Wikimedia

Between resentments and financial difficulties, Arnold secretly approached the British to offer his services. He was placed in charge of fortifications at West Point on the Hudson River, upstream from British-occupied New York City and barring them from sailing upriver. Arnold plotted to sell plans of the fortifications to the enemy and contrived to deliver them into British hands for £20,000. However, his British contact was captured, along with documents incriminating Arnold. He fled just in time to evade arrest. He was made a brigadier general in the British Army, and led soldiers against the American side. The British never fully warmed to him, however, and after the war, he was unable to secure a regular commission. He pursued a variety of ventures, including privateering and land speculation in Canada, before he finally settled in London, where he died in 1801.

The Incredible American Generals that Defined their Eras
General John Sedgwick. Civil War Talk

7. A General More Remembered for His Unfortunate Last Words Instead of His Stellar Record

John Sedgwick (1813 – 1864) was born into a family of Revolutionary War veterans, including one grandfather who had served as a general alongside George Washington. Sedgwick became a respected and competent Union general and corps commander in the Civil War. His kindliness and paternal affection, combined with concern for his soldiers’ well-being, won him the love of his men and the nickname “Uncle John”. Unfortunately, he is more widely remembered for his death and ironic last words, than for any of his life accomplishments or the good service he gave his country in a long military career.

Sedgwick graduated from West Point in 1837, and was commissioned as an artillery officer. In the following decades, he served ably in the US Army, and was still in uniform when the Civil War broke out in April, 1861. He was given a cavalry regiment, and by August, 1861, was promoted to command his own brigade in the Army of the Potomac. The following February, he was put in charge of his own division. He fought bravely in the Peninsula Campaign, and was twice wounded during the Seven Days Battles.

The Incredible American Generals that Defined their Eras
The death of General Sedgwick. Wikimedia

6. Unfortunate Last Words

At the Battle of Antietam, General Sedgwick was sent on a poorly planned charge. His division was shot to pieces, lost 2200 men, and he was hit by three bullets. When he recovered and returned to duty, he was promoted to command his own corps. He won early success with his VI Corps during the Battle of Chancellorsville in 1863, but the battle ended in defeat. In the Overland Campaign in 1864, Sedgwick led his corps in the Battle of the Wilderness. On May 9th, 1864, at the start of the Battle of Spotsylvania Courthouse, he was positioning his artillery, when his troops came under sniper fire and began to get jittery.

The avuncular Sedgwick chided his men for their timidity under single bullets, and wondered how they would react when they confronted massed Confederates on the firing line, and faced full volleys. The men were chagrined, but continued to flinch. So Uncle John Sedgwick continued: “Why are you dodging like this? They couldn’t hit an elephant at this dista…“, at which point his pep speech was interrupted by a sniper bullet that hit him in the face. It struck beneath his left eye, killed him instantly and turned him into the highest-ranking Union battlefield death of the Civil War.

The Incredible American Generals that Defined their Eras
‘Washington Crossing the Delaware’, by Emanuel Leutze. Metropolitan Museum of Art

5. The Patriots’ Low Point in the American Revolution

Washington Crossing the Delaware, painted by German -American artist Emanuel Gottlieb Leutze in 1851, is one of the most iconic images of the American Revolution. It depicts General George Washington and a flotilla of Patriots in boats crossing the Delaware River on the night of December 25 – 26, 1776, for a surprise attack against enemy forces. The portrayal of Washington standing at the boat’s prow, staring determinedly at the enemy shore, while flanked by other Patriot-laden boats, captured imaginations then and since The event was dramatic and worthy of commemoration.

As 1776 drew to a close, the war and the Americans’ armed bid for independence had not been going well for Washington and his Revolutionary forces. The Patriots had been outgeneralled, outfought, and soundly drubbed. Most notably in New York City, where they had only avoided annihilation via a near-miraculous escape. Morale was low, so Washington planned a daring raid to score a quick victory and restore some confidence to the Revolutionary cause. From his base in Pennsylvania, he would cross the nearly frozen Delaware River, to suddenly descend upon and destroy Hessian forces on the opposite bank, in Trenton, New Jersey.

The Incredible American Generals that Defined their Eras
George Washington. Pinterest

4. George Washington’s Unexpected Turn to Humor

The portrayal of George Washington in Washington Crossing the Delaware is true to the essence of what is known of the man. His style was heavy on projecting an aura of detached dignity and a wall of formality that separated him from subordinates. It was not true, however, to Washington’s actual conduct during the crossing: it was one of the rare occasions when the general let down the formality, and cracked jokes. Washington’s cold, hungry, and demoralized trooped clambered into boats on a frigid winter night, made even more miserable by driving sleet. When it was Washington’s turn to get into a boat, he looked at Henry Knox, his overweight artillery chief, and said: “Shift your fat ass, Harry! But don’t swamp the damn boat!

The Incredible American Generals that Defined their Eras
‘The Capture of the Hessians at Trenton, Decemeber 26, 1776’, by John Trumbull. Yale Art Gallery

All things considered, it was not a comedy gem. But any levity from George Washington in public, especially on such a serious occasion, was highly unusual. At first, the men were stunned, and stood around looking at each other in shocked disbelief. Then somebody chuckled, and before long, contagious laughter rippled throughout the entire force, as Washington’s comment was spread and repeated. With their spirits lifted, the Revolutionaries crossed the river, and fell upon the enemy in Trenton, where they killed, wounded, and captured about a thousand men, for the loss of only two dead and five wounded Americans.

The Incredible American Generals that Defined their Eras
George Washington with some of his dogs. History Network

3. A General Who Stopped a War for a Dog

Just about all American presidents have been dog people. Even the ones who might not have been that fond of dogs have often found it convenient to keep a mutt or two in the White House for appearances’ sake, and to project a wholesome image. However, few American presidents were as fond of Man’s Best Friends as was George Washington. America’s first president was a big-time dog lover. During his lifetime, he had dogs from just about every group recognized by the American Kennel Club today.

Greyhounds, French hounds, spaniels, terriers, Newfoundlands, and Briards were just some of the breeds kept by Washington at one time or another. He maintained a pack of fox hunting hounds in a well-kept kennel that had a spring running through it to supply the dogs with fresh water. He personally inspected it twice a day, every morning and evening, when he dropped by to check on his hounds. As seen below, Washington’s love of dogs even led him to call an unexpected truce during the Revolutionary War, in order to return a lost dog to its owner: an enemy general.

The Incredible American Generals that Defined their Eras
The Battle of Germantown. Wikimedia

2. A Great Leader, but a So-So General

George Washington was a great man and a great leader, but only a so-so general who lost more battles than he won. Fortunately for him, the Patriots did not need to outright win the War of Independence on the battlefield, but simply continue the fight until the British finally grew tired and gave up. Even more fortunately for General Washington, the battles he won included the American Revolution’s final and most important battle: the Siege of Yorktown, which ended with the surrender of a British army.

The Incredible American Generals that Defined their Eras
General William Howe. Brown University

The fights he lost included the Battle of Germantown, near Philadelphia, in which a British army led by Sir William Howe defeated Washington and his forces on October 4th, 1777. After the loss, the retreating Americans discovered that their ranks included an unexpected addition: an unknown but clearly well-kept terrier. When they inspected the dog’s collar, the Americans discovered that it belonged to Sir William Howe. The British commander’s dog had wandered into the battlefield, and in the chaos and confusion attached itself to the Americans. The Patriots wanted to keep it in order to taunt the British, but Washington was too classy to keep another man’s dog.

The Incredible American Generals that Defined their Eras
George Washington riding after his hounds at a hunt. Journal of the American Revolution

1. A Touching and Honorable Moment In the Midst of War

George Washington bucked his men and resisted their calls to keep Sir William Howe’s prized terrier. Instead, he sent a messenger under a white flag of truce, across the lines to the British commander. The messenger delivered the dog to Sir William, along with a note that read in relevant part: “General Washington’s compliments to General Howe. He does himself the pleasure to return to him a dog, which accidentally fell into his hands, and by the inscription on the Collar appears to belong to General Howe“.

Howe was impressed by the unexpected gesture from his enemy. The British commander expressed his gratitude to Washington, and described the incident as “the honorable act of a fine gentleman“. The touching episode did not end the war, which continued unabated for years. Nor did it end Howe’s participation in the conflict. However, although he continued to fight and win battles against the Americans, Sir William Howe did so with less enthusiasm than he had exhibited before Washington interrupted the war to return an enemy’s dog.


Where Did We Find This Stuff? Some Sources and Further Reading

American Battlefield Trust – The Death of John Sedgwick

Antietam on the Web – Special Order 191: Perhaps the Greatest ‘What If’ of American Military History

Arnold, Isaac Newton – The Life of Benedict Arnold: His Patriotism and His Treason (1880)

Atkinson, Rick – The Day of Battle: The War in Sicily and Italy, 1943-1944 (2007)

Barthel, Thomas – Abner Doubleday: A Civil War Biography (2010)

Burns, Patrick – American Working Terriers (2006)

Catton, Bruce – The Civil War, Three Volumes in One (1984)

Chernow, Ron – Washington: A Life (2011)

Coffey, Thomas M. – Iron Eagle: The Turbulent Life of General Curtis LeMay (1986)

Council on Foreign Relations – TWE Remembers: Secret Soviet Tactical Nuclear Weapons in Cuba (Cuban Missile Crisis, a Coda)

Doubleday, Abner – My Life in the Old Army (1998 Edition)

Elting, John Robert – Amateurs, to Arms! A Military History of the War of 1812 (1995)

Encyclopedia Britannica – Benedict Arnold

Encyclopedia of Greater Philadelphia – Trenton and Princeton Campaign (Washington’s Crossing)

History Collection – 10 Significant Things About the Culper Ring, George Washington’s Most Important Spy Network

History Daily – When George Washington Ordered a Ceasefire to Return a Dog

James, Dorris Clayton – The Years of MacArthur: Triumph & Disaster, 1945-1964 (1985)

Kilmeade, Brian, and Yaeger, Don – George Washington’s Secret Six: The Spy Ring that Saved the American Revolution (2013)

Manchester, William – American Caesar: Douglas MacArthur, 1880-1964 (1978)

Politico, December 24th, 2015 – George Washington Crosses the Delaware, Dec. 25, 1776

Psychology Today – George Washington: President, General, and Dog Breeder

Sears, Stephen W. – To the Gates of Richmond: The Peninsula Campaign (1992)

Task Force Baum – The Hammelburg Raid

Zaslow, Morris – The Defended Border: Upper Canada and the War of 1812 (1964)