7 Legendary American Generals, 7 Legendary Mistakes
7 Legendary American Generals, 7 Legendary Mistakes

7 Legendary American Generals, 7 Legendary Mistakes

Gregory Gann - August 9, 2017

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.