Gambling through Defeat and Victory - The Winter Gamble

Darkness Descends

The month of December 1776 was indeed a month that tried men's souls. The British had the Continental Army on the run since they invaded Long Island in the summer. The "victory" at Harlem was the closest the hapless Americans came to checking Lord Howe's onslaught.  The only thing between Washington and an early British victory to end the rebellion was, well, Lord Howe. Smart strategic move after move, well-executed naval landings, precision tactics, highly professional sieges were the hallmark of Howe's offensive. But he moved all too slowly and time after time Washington escaped the noose.

Cornwallis crossed with five thousand crack troops to begin
the route through the Jerseys

Winter Quarters

Lord Cornwallis

 By late December Washington's army was safe across the Delaware River and expecting to defend the nation's capital, Philadelphia. He had less than 2500 "effectives," and that number would soon drop with many enlistments ending in January and the desperately needed replacements not arriving until early the next year (if at all). The Continental Army lacked supplies of all kinds, especially
clothing.  Not just winter clothing - any clothing!  But Washington had help from Howe, who halted General Cornwallis 5,000 crack troops at the Delaware. Washington's men had confiscated every civilian boat for miles along the river and Cornwallis had to wait for the British pontoon trains before crossing.  Instead, Howe, thinking Washington beaten, ordered his army into "winter quarters" and himself scurried back to New York and his mistress. Cornwallis' wife meanwhile was reported ill and he headed to New York to catch a ship to England before the winter made crossing impossible. To guard his New Jersey holdings, Howe left brigade-sized garrisons at Princeton, Brunswick, Bordentown, and Trenton.

An Army at rest and an Army formed

General John Sullivan

As soon as he escaped Cornwallis' onslaught, Washington began to think about his next move.  Congress abandoned the capital and fled to Baltimore. Congress also offered him near-dictatorial powers, which he eschewed. Then, the help he had counted on, then dismissed, suddenly arrived.  General John Sullivan, returned from British captivity, led the division of General Charles Lee across the Delaware and joined Washington near Yardley, New Jersey. Washington then decided to act on his plan,  he would gamble on a surprise attack against the British garrisons closest to the Delaware:  Bordentown and Trenton.  Washington's bold gamble required meticulous planning, daring, and luck. His first bit of luck was Sullivan's arrival.  His second, his ability to convince the troops to extend their enlistments long enough to enable his plan. Washington personally met with the men and his sincerity and obvious dedication to them and the cause turned the hearts of just enough. The third would be the weather, and lastly, maintaining the element of surprise during a time when not just Loyalists but even despondent patriots might give him over to the British.  Spies were everywhere.



The Crossing

Washington hid his movements from Loyalist spies and got his army to McGonkey's Ferry on the evening of the 25th of December.  The weather was cold with snow flurries, but the ice had not yet formed on the river.  The crossing commenced after dark but delay after delay put Washington's timetable off.  He hoped to march some nine miles downriver and surprise the Hessian garrison under Colonel Johan Rall at dawn.  The key was the guns.  Henry Knox assured him he'd be able to get the 18 cannon across.  But the snow picked up in intensity and ice floes began to form.  With each wave of boats that crossed in the darkness, the danger grew. But Colonel John Glover's Marblehead sailors, the famed Gloucester Regiment, exceeded the heroics of Long Island.  A crossing delayed would not be a crossing denied... at least at McGonkey's.  Further downriver two other divisions of Pennsylvanians under Generals Ewing and Cadwallader were supposed to cross and seize Bordentown and assist at Trenton. But the ice floes had thickened to where neither could cross that night.  That part of Washington's gamble had failed.

The Miracle

Washington's forces did not fully cross until well into the wee hours.  Then began the night
march in two columns, one along the river road and another, which Washington joined, moved further inland. The men, cold, wet, and tired, struggled over rugged, rocky, and wooded land. Limbs frozen and half-blind by the elements, the soldiers wore patches of white paper to guide them in the dark.

All the time, Washington kept hoping the other columns could cross and that the Hessians were not alerted and waiting. His worst fears were realized in the former but his greatest expectations realized in the latter.  Arriving well into the early morning light, the Americans were amazed to find the little town still sleeping and the weather clearing. The sound of a cannon signaled the two-pronged attack. Surprised, the Hessian professionals formed up best they could to meet the invaders but within an hour the battle was over. Rall, the enemy commander, fell mortally wounded and his men soon grounded arms.  Not one American had died and only a few were wounded. Washington's gamble succeeded... but his winter gambling had only just begun.

Continentals rush a Hessian gun to open the battle

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.