7 Legendary American Generals, 7 Legendary Mistakes

7 Legendary American Generals, 7 Legendary Mistakes

Gregory Gann - August 9, 2017

War is an unforgiving line of work. A bad decision or an unlucky series of events can transform a formidable general’s reputation into synonym for tremendous failure. Europe, for example, trembled when Napoleon crushed the fearsome Prussian Army, but the petite empereur is best remembered for staging monumental snowball fights on the way back from Moscow. Because that’s what happens when a successful commander fails on the field of battle… usually.

Occasionally, a disastrous mistake, or three, does not ruin an officer’s glorious reputation, and this group of American military legends got a reprieve from history and a second chance they may not have deserved.

Douglas MacArthur – Battle of the Philippines (1941)

The General

Douglas MacArthur is a controversial figure in American military history, and his career includes some of the United States’ greatest triumphs and tragedies. He fought with distinction in World War I, modernized the U.S. Military Academy, and irreparably stained his honor during the Bonus Marches. Commander of sweeping World War II campaigns, overseer of Japan’s occupation, and crafter of the Korean War landing at Inchon, MacArthur was forcibly retired after testing the boundaries of civilian control over the military.

7 Legendary American Generals, 7 Legendary Mistakes
General of the Army Douglas MacArthur, 1945. Wikipedia

The Blunder

Beginning approximately ninety minutes after the bombing at Pearl Harbor, MacArthur was repeatedly warned to expect an attack. Despite these warnings, and official orders to launch an immediate offensive, MacArthur neither readied his defenses nor obeyed orders to assault Formosa. Thus, when Imperial Japan attacked, MacArthur’s ineptitude set the stage for the disastrous Battle of the Philippines, arguably the worst military defeat in United States history.

Battle of the Philippines

Shortly after the attack at Pearl Harbor, MacArthur was warned (informally) to anticipate an attack. MacArthur, however, chose not to alert his command. Brigadier General Sutherland, MacArthur’s chief of staff, passed the news onto General Brereton, commander of the Far East Air Force (FEAF) and MacArthur’s primary offensive weapon, but no other instructions. For unknown reasons, Sutherland would block Brereton from speaking to MacArthur for the next six and half hours.

General Brereton knew an immediate attack could catch Japanese aircraft on the ground, but only if his bombers reached Formosa before the enemy began their own assault. The general’s instincts were better than he realized. A thick fog bank had rolled over Formosa and delayed Japan’s offensive. An attack would have annihilated the larger Japanese air force on the ground. Unfortunately for the Philippines, MacArthur issued no orders of any kind.

Orders activating Rainbow 5, the offensive war plan, arrived an hour later. Rainbow 5 called for an immediate offensive using the FEAF exactly as Brereton envisioned. Despite receiving official orders, MacArthur did not issue instructions to Brereton or alert the base’s defenses. The hours dragged on. Brereton feared an imminent attack and ordered his aircraft aloft to prevent their destruction on the ground. Two hours later, MacArthur finally emerged from seclusion and reluctantly ordered attacking Formosa. Brereton ordered his aircraft to land and refuel. The fog bank that delayed Japan’s air assault, however, had dissipated while MacArthur dithered, and Japanese aircraft attacked while the FEAF refueled.

MacArthur’s complete and utter failure to ready his command for defense or to initiate an attack, as his orders dictated, crippled American airpower and laid the Philippines open to invasion. Excepting the escape of fourteen B-17s to Australia, the FEAF was completely destroyed. The reason for MacArthur’s lengthy indecisiveness and failure to follow orders is not known. Unlike the debacle at Pearl Harbor, there was no official inquiry into the devastating loss at the Battle of the Philippines. Years later, Sutherland and Brereton publicly blamed each other, and MacArthur issued a statement stating he recalled no recommendations to attack Formosa.

Insider Guide: Was General McArthur Really an American Hero or Overrated Narcissist?

7 Legendary American Generals, 7 Legendary Mistakes
General of the Army Omar Bradley, 1st Chairman of the Joint Chiefs of Staff. Wikipedia

Omar Nelson Bradley – Battle of the Falaise Pocket (1944)

The General

Although General Omar Bradley is not the most famous American general, few officers can match his achievements. Bradley’s early career was unremarkable, but he developed a reputation as a quiet, extraordinarily capable, officer. He climbed the ranks steadily, oversaw the development of the United States’ first airborne division, led the Second Corps in Tunisia and Sicily, commanded the US First Army in Operation Overlord, and finished World War II as the commander of the Twelfth United States Army Group, the largest American force ever fielded. Following a four-year stint as the first Chairman of the Joint Chiefs of Staff, Bradley retired as a five-star General of the Army in 1953.

The Blunder

On August 13, 1944, the German armies in Normandy were nearly surrounded. Bradley ordered the units completing the encirclement of the German armies to halt or retreat. This decision set in motion a chain of events that allowed many of the Reich’s soldiers and commanders to escape, regroup, and counter-attack during the Battle of the Bulge later that year.

Falaise Pocket

Two months after the Allies invaded France, Germany’s Army Group B faced a strategic nightmare. The fight against allied forces worsened daily, yet Hitler, rather unsurprisingly, refused to allow the army to retreat. A pincer was closing around the Reich’s Army Group, and the Allied plan was as subtle as a sledgehammer. The encircled German armies would cease to exist in a merciless hail of artillery and airstrikes followed by a ground attack from all sides.

It should have worked. It very nearly did work. Elements of Montgomery’s 21st Army Group closed around the north as Bradley’s armies and General Haislip’s XV corps hastened to meet them from the south, creating the “Falaise Pocket.” As the vise tightened around the German armies, however, Bradley grew concerned. General Patton had nearly connected with Montgomery’s Canadian troops, but Bradley believed Patton had moved too quickly, creating an overextended and dangerously thin defensive line. Adding to his worries, Bradley thought “friendly fire” would explode between the American and Canadian forces when they connected. He ordered Patton to stop advancing and fall back. Patton protested, to no avail, but followed orders. This created a gap allowing German troops, in complete defiance of their Fuhrer’s orders, to flood through and escape.

The gap was eventually shrunk, and Army Group B ceased to exist; a tremendous victory for the allies, but incomplete as a large chunk of Germany’s 7th Army slipped out of the noose. The exact number of German troops who escaped is unknown, and estimates range between twenty and fifty thousand. Near the end of 1944, these soldiers formed a large component of the Reich’s final western offensive, which delayed the Allied advance and contributed to dragging out the war. Characteristically, Bradley later admitted a mistake was made. Uncharacteristically, he laid the blame squarely on Montgomery’s shoulders, stating the British General had moved too slowly.

7 Legendary American Generals, 7 Legendary Mistakes
Lieutenant General Lewis Burwell “Chesty” Puller,

Lewis Burwell “Chesty” Puller – Battle of Peleliu (1944)

The General

Chesty Puller’s reputation in the United States Marine Corps is unrivaled. Ask any leatherneck who Chesty Puller was and you’ll be transfixed with a thousand-yard stare that promises an explanation only if you’re polite. No one influenced the US Marine Corps more than Puller, whether by conduct, leadership, combat prowess. Puller’s resume includes fighting Haitian guerillas in the 1920s, the Imperial Japanese Army throughout World War II, and the North Korean and Chinese armies during the Korean War. He developed a towering reputation through a depth of combat experience that few contemporary commanders could match, habitually destroyed his opponents, and led from the front.

The Blunder

Despite overwhelming evidence of the enemy’s numerical superiority, Puller uncharacteristically wasted the lives of Marines in a series of assaults against the exceptionally well-fortified Japanese Army during the Battle of Peleliu. Puller compounded his error by refusing to ask for reinforcement from the nearby Army 81st Infantry Division.

Battle of Peleliu

In September of 1944, the United States Marines invaded the isle of Peleliu, furthering America’s strategy in the Pacific theater by seizing control of an airbase that belonged to Imperial Japan. The Marines captured the airport on the second day of the battle, but securing the main objective is not the same thing as conquering an island. Particularly when American intelligence vastly underestimated the number of enemy soldiers defending Peleliu. Nearly 11,000 Japanese soldiers had heavily fortified the island’s interior coral promontories, and surrender was not on their minds.

Commanding the 3,000 men of the 1st United States Marine Regiment, Puller unexpectedly attacked the entrenched enemy forces in the face of their overwhelming numerical superiority for six days straight. American casualties skyrocketed, for little or no gain, yet Puller sent wave after wave of Marines into this fiasco. He ignored his battalion commander’s descriptions of the enemy’s well-developed defenses, their reports of the terrain’s ruggedness, and rejected their pleas for reinforcements. The Army’s 81st Infantry Division was literally sitting in a nearby ship waiting to deploy, but Puller refused to ask for assistance.

On the sixth day of the battle, General Roy Geiger decided enough was enough. Geiger pulled Puller and his regiment out of combat and decided the better part of valor involved leaving the Japanese in their bunkers forever. That sort of thing happens when you use bulldozers as weapon of war, and end the threat of soldiers by sealing them in their defenses alive.

Chesty Puller’s Marines suffered 70% casualties. He ignored the advice of subordinates, underestimated the enemy, and refused to ask for help from the Army, cause, you know, Semper Fi.

7 Legendary American Generals, 7 Legendary Mistakes
Official U.S. Navy Portrait of Fleet Admiral William F. Halsey, Jr. Wikipedia

William Frederick “Bull” Halsey Jr. – Typhoon Cobra (1944)

The General

The word “fear” was scared to work its way into Admiral Halsey’s vocabulary. He captained incredibly unsafe torpedo boats throughout WWI, earned his aviator wings before accepting command of an aircraft carrier, commanded the task force that launched the Doolittle Raid, and fought the Imperial Japanese Navy throughout the Pacific Ocean. Halsey embodied the bravery and aggressiveness that officers and enlisted strive to achieve, and no one can argue that he set an example for anyone who followed him. The sailors who drowned because Halsey’s fearlessness included ignoring the danger of mother nature at its angriest, however, probably hoped he’d get a reprimand at least.

The Blunder

Despite advance receiving warning, Admiral Halsey allowed a typhoon to ravage his command. The storm killed numerous Sailors, damaged or sunk ships and aircraft, yet Halsey managed to escape punishment. The typhoon, dubbed “Typhoon Cobra” or “Halsey’s Typhoon,” swept over Halsey’s command, the United States Navy’s Third Fleet, on December 17th, 1944, and the fearless Admiral’s stubbornness was the primary culprit.

Typhoon Cobra

In December 1944, Third Fleet was busy refueling off the coast of the Philippines in preparation for a renewed offensive against the Japanese. Weathermen in Hawaii reported the formation of a storm to the west and predicted it would follow a northerly path, missing the fleet. Halsey’s meteorological staff concurred, and Third Fleet remained on station. Evidence, however, soon proved the weathermen wrong. The sea turned choppy and rough. Winds increased. Halsey’s aerologist, Commander George F. Kosco, re-evaluated, predicted a new path for the typhoon, and concluded the storm was stronger than previously believed, increasing in intensity, and closing in on the fleet.

Following Third Fleet’s refueling, Halsey’s command was scheduled to participate in the assault on Luzon. The Admiral was eager to depart, and the storm threatened to delay his command. If Halsey moved the fleet out of the storm’s new projected path, Third Fleet’s schedule would be ruined. Halsey decided to gamble that his aerologist was wrong, and ordered Third Fleet to hold their positions. He believed the storm would taper off, and refueling operations could renew with only a slight delay. The Admiral was not correct.

Over the next several days, Third Fleet’s losses included 778 dead Sailors, 146 destroyed aircraft, and three sunken destroyers. A Navy court of inquiry later found that Admiral Halsey “committed an error in judgment,” but did not recommend sanctions. Interestingly enough, Admiral Halsey’s superior and close friend, Fleet Admiral Nimitz attended the inquiry.

7 Legendary American Generals, 7 Legendary Mistakes
General Jackson photographed at Winchester, Virginia 1862. Wikipedia

Thomas Jonathan “Stonewall” Jackson – Seven Days Battles (1862)

The General

When it comes to Confederate generals, only one name competes with Robert E. Lee’s: Stonewall Jackson. Stonewall repeatedly outsmarted or outfought the Union at the Battles of Bull Run, Harper’s Ferry, and Fredericksburg. His rapid movements and skillful maneuvering throughout 1862’s Valley Campaign remain a staple of tactical classes at military institutions worldwide. Unlike other commanders on this list, Jackson was not single-handedly responsible for an unmitigated disaster. Several Confederate generals erred throughout the Seven Days Battles, but Jackson’s performance was so ridiculously sub-par, and insanely out of character, that it played a major role in the Union Army’s escape.

The Blunder

From June 25 to July 1, 1862, Confederate General Robert E. Lee pushed Union General George B. McClellan and the Army of the Potomac away from Richmond, VA, but did not inflict crippling losses due to Jackson’s repeated, and often inexplicable, failures. Throughout four of the six battles, Jackson either did not arrive on time or attack as ordered.

Beaver Dam Creek, June 26

Lee’s plan hinged on Jackson attacking the Union’s vulnerable north flank early in the morning. This attack was the signal for Generals Longstreet and A.P. Hill to launch their respective assaults, but Jackson did not arrive until late afternoon. Although Jackson notified Lee of his delay, fighting exploded when A.P. Hill attacked early. When Jackson arrived, he made the mystifying decision to bivouac his army rather than attack as ordered. Granted, Jackson was concerned about his men’s fatigue, but the battle was raging within earshot.

Gaines’s Mill, June 27

There are mitigating circumstances for his late arrival at Beaver Dam Creek, but there’s no excuse for Stonewall’s performance at Gaines’s Mill. Lee launched the largest Confederate attack of the war, roughly 57,000 men, and Jackson was ordered to flank the enemy and attack from the north. A maneuver he and his experienced corps accomplished repeatedly in the Valley Campaign. Jackson, however, got lost, dithered on arrival, and did not attack until 4:30 p.m., severely reducing Union losses.

Savage’s Station, June 29

Savage’s Station was one of those rare opportunities where a crafty commander could destroy the bulk of his enemy’s army. Union General George “There’s No Battle I Can’t Run Away From” McClellan was retreating, and Lee intended to crush the Army of Potomac between General Magruder and Stonewall Jackson’s forces. Jackson, however, crept forward at a snail’s pace and did not arrive until 2:30 a.m. the following day, which allowed the Union Army to escape.

Battle of Glendale, June 30

This was Lee’s last chance to destroy his enemy. The Union Army’s command structure was wrecked, morale was non-existent, and its defensive line was ragged. War, however, is unpredictable, and half of Lee’s commanders utterly failed. General Huger was delayed and never showed. Magruder wandered around confusedly until mid-afternoon. Jackson, arguably Lee’s best and most aggressive commander, spent the day skirmishing with the Union in meaningless artillery duels, attempting to rebuild an irrelevant bridge, and generally not attacking the enemy.

7 Legendary American Generals, 7 Legendary Mistakes
General of the Army Dwight David Eisenhower, 1945. Wikipedia

Dwight D. “Ike” Eisenhower – Operation Husky (1943)

The General

General Dwight “Ike” Eisenhower commanded campaigns larger than most nation’s entire wars, and many of his decisions shaped the contemporary world. Five-star general in the U.S. Army, Supreme Commander of the Allied Expeditionary Forces in Europe, Eisenhower planned and/or commanded every major allied campaign throughout World War II in Africa, Italy, and Western Europe.

The Blunder

Generally speaking, destroying an opponent’s army is a primary objective. If you take a chunk of their territory, but allow their army to escape, it tends to come back to haunt you. Apparently, Eisenhower needed reminding of this maxim while planning the invasion of Sicily in 1943. Ike deliberately chose not to establish a beachhead in Southern Italy to prevent the Axis forces from escaping Sicily, claiming he saw no advantage to the plan. This decision allowed Axis armies to slip through Eisenhower’s fingers in one of the smoothest, well-planned, evacuations throughout World War II.

Operation Husky

Popularized in the movie “Patton,” the invasion of Sicily is best known as a competition between the incredibly aggressive American General George S. Patton and the calculating British General Bernard Montgomery. Unfortunately, this narrative detracts from the operation’s mammoth size and accomplishments. Spread out over 105 miles, Operation Husky landed seven divisions at twenty-six beaches in an immense amphibious assault that foreshadowed Operation Overlord the following year. No one had ever attempted an amphibious invasion at such a scale, and the lessons learned by the Allies played a massive role in their future success at Normandy.

Eisenhower, as the overall commander, was responsible for planning the operation with the assistance of his senior commanders. British General Sir Harold Alexander, Eisenhower’s second in command, argued for diverting forces midway through the campaign to create a beachhead on Italy, thereby sealing the Axis’ armies fate on Sicily. Eisenhower hated the idea, preferring to keep the troops close at hand. Alexander dragged Churchill into the argument, who supported the creation of a bridgehead enthusiastically. Eisenhower, in turn, appealed to the Army’s Chief of Staff, George C. Marshall, who backed Ike up in refusing the plan.

The conquest of Sicily took a little over a month, and the Allies were unquestionably victorious. Eisenhower’s refusal to establish the Italian beachhead, however, came with a cost. Roughly 110,000 German and Italian troops, 135 pieces of artillery, 14,332 vehicles, 47 tanks, and over 1,000 tons of ammunition had escaped to Italy. This force of soldiers and equipment strengthened Italian defenses on the eve of the Allies mainland invasion and helped drag the campaign on for months, when it should have never left the island it was defending.

7 Legendary American Generals, 7 Legendary Mistakes
Emanuel Leutze’s painted depiction of General Washington crossing the Delaware River in 1776. Mount Vernon.org

George Washington – Battles of Long Island and Brandywine (1776 and 1777)

The General

General George Washington is the O.G. of American military legends. He fought the most elite military in the world, and, despite the incredible forces working against him, Washington won. The disastrous first two years of the American War of Independence make Washington’s achievement all that much more impressive. Few commanders can rebound from repeated losses and overcome obstacles such as poor, often non-existent, supply lines, an undisciplined and unreliable army, and their own tactical incompetence. Sure, George annihilated a bunch of drunken Hessians in an amazing surprise attack on Christmas morning in 1776, but in his first two major engagements against the British regular army the Continental Army didn’t fail their commander as badly as Washington failed his army.

The Blunder

General William Howe defeated Washington with the exact same tactical maneuver at two different battles. Worse, the battles took place a year apart. Washington had plenty of time to understand the tactics Howe used to defeat him, but apparently, learning wasn’t high on George’s priority list yet.

The Battle of Long Island

Washington knew New York City was a priority for the British, and the British did not disappoint him. General Howe landed across from Manhattan and spent most of July and August assembling his army. Inexperienced at managing a large army and unsure where the British would attack, Washington split his forces, sending half his army to defend Long Island while holding the rest in Manhattan. When the British invaded Long Island in late August, Washington believed the attack was a feint and neither attacked nor reunited his army. This gave the British time to ferry most of their army across the harbor, and concentrate their attack on one part of the divided American forces. Eventually, Howe launched a frontal assault. This attack actually was a diversion. Under the cover of darkness, Howe had moved most of his army around Washington’s flank the night before, and his attack routed the surprised and vastly outnumbered, Americans.

The Battle of Brandywine

Washington and Howe met again a year later in southeastern Pennsylvania. Howe intended to capture Philadelphia, seat of the rebel Congress. Aware of Howe’s location and goal, Washington interposed the Continental Army at Brandywine Creek. Howe responded by, and raise your hand if this sounds familiar, feinting a frontal assault while moving his troops around Washington’s right flank. Not only was this the same tactic that defeated Washington at Long Island, the maneuver was arguably more successful the second time. British troops reached the right flank’s rear before attacking. Not to be outdone by Howe, George repeated his Long Island tactics too, and hastily retreated.

The British captured Philadelphia two weeks later. Washington unsuccessfully fought to relieve the city, and retreated to Valley Forge for the winter. Unfortunately for Howe, Washington and the Colonial Army transformed over the months that followed. They emerged from Valley Forge a renewed, professionalized, army guided by a startlingly capable general, and the rest, as they say, is history.