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
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.