Gambling through Defeat and Victory

The Gambler

The Gambler

Apologies to Kenny Rogers and no, His Excellency did not have a betting problem.  Although as a landed Virginia planter he was no stranger money won and lost at the horse race or whist table. Ever the champion
of order and probity, 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 settled in on a risk-averse Fabian strategy for the war, Washington understood that a successful commander must be ready to take calculated risks. Since his Army was almost always out-manned and outgunned, this need to take risk came all too often. At Boston in 1775, Washington rolled the dice three times:  outfitting ships to take on the British Navy, dispatching troops to Canada, and sending a small band to capture Fort Ticonderoga and its powerful battery of guns. The Canada campaign failed, and his navy's efforts only pointed out the need for a Continental Navy, but Ticonderoga fell to a surprise attack.  The latter 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 the success it was.

Heavy guns from Ticonderoga 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 a thrust at New York. Not yet the largest city in North America, New York was strategically important because of its location and its excellent harbor. In addition, New York had a larger Loyalist base than in New England. Washington rushed his forces south in anticipation of an invasion by sea. When the British seized Staten Island, Washington risked dividing his forces and deployed about a third of his army on Long island to stop an anticipated phased approach to taking the Island of New York (Manhattan). The result was a sound walloping as the vastly outnumbered forces on Long Island only escaped complete destruction by the further gamble of a night move during a storm in the face of the enemy. Two principles of war thrown out in desperation. Washington gambled in the secret war as well - sending the unprepared Captain Nathan hale behind British lines and launching the "wonder weapon" (not) - the submarine Turtle. The last New York gamble was leaving a considerable body of valuable troops at the Fort named Washington on upper Manhattan. This was done to maintain a foothold on the island in the hope of using it to retake the island. The result was the loss of the fort and its men, who could have done better work in the upcoming campaign for the Jerseys. 

Americans faced overwhelming British forces at Long Island

The South Brings Triumph

That would be south (some might say central) Jersey. Most Americans know about Washington crossing the Delaware and a few know it led to a victory at Trenton. But few realize that this unlikely victory was one of Washington's greatest gambles.  His forces were spent and demoralized after a chaotic retreat across the Jerseys. Washington's army abandoned Fort Lee to General Cornwallis and skedaddled from Hackensack, through Newark,  New Brunswick, and Princeton. In December, Washington managed to get his meager force across the Delaware to the safety of Pennsylvania. After a long year of fighting, with barely fifteen hundred underfed and equipped "effectives" and a demoralized nation ready to give up the glorious cause, Washington's situation was bleak. Enlistments were running out, supplies nowhere to be had, and a panicky Congress had fled the capital, Philadelphia. To cap it off, 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 entire world knew the end was near.

General Howe

 Nobody would have blamed Washington for taking his meager forces into winter quarters and try to come back in the spring. That's what the British commander was expecting and doing himself.  To the consternation of many of his senior officers, General William Howe placed his army into winter quarters just when he had Washington beaten. Brigade sized elements garrisoned Princeton, Trenton, and Bordentown, while the rest of Howe's army remained in or near the comforts of New York. Fortunately, Lee's division made it to Pennsylvania without their commander, providing Washington just the boost he needed to try a desperate gamble to save the revolution from ending that winter. How he succeeded in this gamble will be our next discussion.