Gambling through Defeat and Victory

The Gambler

The Gambler

Apologies to Kenny Rogers, and no, His Excellency did not have a gambling problem. Although as a landed Virginia planter, he was no stranger to money won and lost at the horse race or whist table. Ever the champion of order and integrity, Washington knew that excessive gambling was problematic. He is quoted on the subject: "Gambling is the child of avarice, the brother of iniquity, and the father of mischief." But during the time of the Yankee Doodle Spies, it was sometimes a necessity, at least on the field of battle.

The North and Early Success

Even as he adopted a risk-averse Fabian strategy for the war, Washington understood that a successful commander must be willing to take calculated risks. Since his army was almost always outnumbered and outgunned, the need to take risks arose frequently. In Boston in 1775, Washington took three major chances: outfitting ships to challenge the British Navy, dispatching troops to Canada, and sending a small force to capture Fort Ticonderoga and its formidable artillery. 

The Canada campaign failed, and his navy's efforts highlighted the need for a Continental Navy, but Ticonderoga was taken by a surprise attack. This victory gave the Americans control of the largest fortress in the colonies and, more importantly, the heavy guns the Continental Army needed to make the siege of Boston a success.

Heavy guns from Ticonderoga were dragged
across snowy mountains to Boston

The Middle Brings Failure

After Boston fell, the British threatened the middle states (or colonies, as you prefer) with an attack on New York. Not yet the largest city in North America, New York was strategically important because of its location and its excellent harbor. Additionally, New York had a larger Loyalist base than New England. Washington hurried his forces south in anticipation of a sea invasion. When the British took Staten Island, Washington risked dividing his forces and deployed about a third of his army on Long Island to stop an expected phased approach to capturing Manhattan. 

The result was a severe defeat, as the vastly outnumbered forces on Long Island only escaped total destruction by taking the risk of a night move through a storm while the enemy was nearby. Two principles of war were abandoned out of desperation. Washington also gambled in the secret war — sending the unready Captain Nathan Hale behind British lines and launching the "wonder weapon" (not) - the submarine Turtle. 

The last gamble in New York was leaving a sizeable force of valuable troops at the fort named Washington on upper Manhattan. This was done to keep a foothold on the island, with the hope of retaking it later. However, the result was the loss of the fort and its troops, who could have been more useful in the upcoming campaign for the Jerseys. 

Americans faced overwhelming British forces at Long Island

The South Brings Triumph

That area would be south (some might say central) Jersey. Most Americans are familiar with Washington crossing the Delaware, and a few know it resulted in a victory at Trenton. But few understand that this unlikely win was one of Washington's biggest gambles. His forces were exhausted and demoralized after a chaotic retreat across the Jerseys. Washington's army abandoned Fort Lee to General Cornwallis and hurriedly moved from Hackensack through Newark, New Brunswick, and Princeton. 

In December, Washington managed to get his small force across the Delaware to safety in Pennsylvania. After a tough year of fighting, with barely fifteen hundred underfed and poorly equipped soldiers and a demoralized nation ready to give up the glorious cause, Washington's situation was dire. Enlistments were ending, supplies were scarce, and a panicked Congress had fled the capital, Philadelphia. To make things worse, the British captured Washington's second-in-command, General Charles Lee, in a daring cavalry raid. Those were the times that tried men's souls, and the whole world thought the end was near.

General Howe

 Nobody would have blamed Washington for taking his small forces into winter quarters and trying to come back in the spring. That's what the British commander was expecting and doing himself. To the alarm of many of his senior officers, General William Howe put his army into winter quarters just when he had Washington beaten. 

Brigade-sized units garrisoned Princeton, Trenton, and Bordentown, while the rest of Howe's army remained in or near the comforts of New York. Luckily, Lee's division made it to Pennsylvania without their commander, giving Washington the boost he needed to try a risky gamble to save the revolution from ending that winter. How he pulled off this gamble will be our next discussion.