An American Revolution Character Lesson 

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The Learners versus the Learned
Subject: American History
Trait: Continual Learning

The year was 1776. The setting was the North American British colonies. The big event was a rebellion against the mother country by some troublemakers who were discontent with British rule.  The outcome would reshape the modern world.

The question I’d like to answer is not whether the British or the Americans were right in their cause – many American colonists sided with their mother country and fought for the British. Similarly, many British argued in their Parliament against the war. The question I’d like to pose is:

“Why did the most powerful, well-trained army on the planet lose a war to an army that seemed inferior in every way?” 

Our answer to this question just might yield some insight into success and failure beyond warfare. And if you sometimes feel inadequate, like everyone else is more talented, better trained, and more educated than you, perhaps you can pick up some tips that can give underdogs an edge.

To set the stage, let’s first grasp just how superior the British forces were.  

So why did the American troops ultimately win? Many reasons could be discussed, but I’d like to suggest one that stood out to me in reading David McCullough’s respected book on the beginnings of the Revolutionary War, titled simply 1776. Here’s my key observation:

The Revolutionary War was a contest between the learned (the British) and the learners (the Americans). The British were overconfident because they were well-equipped, well-trained, and knew how to fight. They thought they knew much more than they’d ever need to know to defeat the pitiful American army, deriding them as “the country people,” “the rebels,” “a preposterous parade,” or a “rabble in arms.” (25) Being learned can be a great thing, but they had apparently stopped learning.

The American leaders, by contrast, were avid learners. They knew they didn’t know everything about warfare and were thus hotly pursuing whatever wisdom they could pick up from anyone and anywhere. 

Here’s how “the learners versus the learned” played out in two decisive battles.

The Battle for Boston, March 4, 1776

The British troops, under the command of General Howe, had taken control of Boston, fortifying it to the extent that many felt it could never be successfully attacked. Howe was one of the most respected, distinguished officers in the King’s service. (76) He was fully assured that he had nothing to fear from the ragtag American army. As General Howe wrote to his superiors, “We are not under the least apprehension of an attack on this place from the rebels by surprise or otherwise.” (72) The British officers lived comfortable lives in Boston, where the officers and their ladies were entertained by plays and balls and held feasts where they drank wine and ridiculed the pathetic American troops. (74)

The American army wasn’t faring as well. It was January, miserably cold, and most lived in makeshift tents without winter clothing. (81) They had little gunpowder, inadequate money to pay the troops, and there weren’t even enough guns for the new recruits. (24,79) Washington feared that if the British discovered their dire situation, they would attack immediately and end the war.

Fortunately for the Americans, the British failed to gather adequate intelligence. They failed to catch wind of a daring two month journey led by the twenty-five year old Colonel Knox to snatch over 120,000 pounds of weapons, including mortar and cannon, from Fort Ticonderoga in Upstate New York and transport them through blizzards, over mountains and freezing lakes, to arrive just in time for the attack. (82-85)

The British leaders were educated in military studies, both in formal classrooms and in live combat. But they saw no need to continue their education. That would prove to be their downfall. Howe took no interest at all in General George Washington. Typically, military leaders gather all available information on their enemies. They want to know how they think, what they fear, what they love, in order to predict their next moves. But their degrees and experience made them comfortable, overconfident, and smug. (78)

Washington and his forces by contrast were learners. Washington gathered wise people around him, as he put it, “to have people that can think for me.” (86, 87) They decided to occupy the strategic twin hills of Dorchester, from which they could threaten both the British soldiers in Boston and their ships in the harbor.  Cannons shot from the hills could reach both. Washington learned from spies that Howe had sworn that if the American army occupied Dorchester, he would retaliate by attack them, which is precisely what Washington wanted. He’d much rather attack Howe’s troops from the advantageous positions of Dorchester than to attack the fortified city of Boston. (86, 87)

But one problem remained – a big one.  If the British saw the Americans clamoring up Dorchester’s hills, they’d attack before the Americans had a chance to fortify the hill. And how do you fortify a hill quickly in the middle of winter? You can’t shovel frozen ground to make your fortifications. Once again, continuing education came to the rescue, in the form of Rufus Putnam, a farmer and surveyor by trade, who read of a useful scheme in an artillery text by a British professor. Putnam showed the plan to his superiors, who in turn took him to Washington.  The scheme involved building the fortifications and transporting them up the hills overnight  by oxen and massive manpower, so that the next morning the British would awake to find Dorchester’s hills occupied with 3,000 men, armed with guns and cannons, and fortified. (88,89)

Four days prior to the attack, a spy warned the British of an impending attack from Dorchester, but nobody took the warnings seriously. They would be warned again, but to no avail, just more evidence they were more learned than learners. (90,91-93)

So Saturday evening, March 2, the American army bombarded Boston with cannons. The British responded with cannon fire. On Sunday, the firing resumed, but it was all just a distraction, so that when the cannons roared once again on Monday night, they covered the sound of 800 oxen, hundreds of carts and wagons, heavy cannons, and fortifications moving quickly and orderly up the hills. Fortunately or providentially, they were aided by the light of a full moon, unseasonably mild weather , and a foggy haze that covered the thousands of soldiers in the low lands before they ascended. (88,89)

The British awoke the next morning to behold what appeared to be a miracle, or from their perspective, a nightmare. They were completely and utterly astonished. General Howe exclaimed, “My God, these fellows have done more work in one night than I could make my army do in three months.” One British officer wrote that “This is, I believe, likely to prove as important a day to the British Empire as any in our annals.” Referring to the fortifications, he marveled, “They were all raised during the night, with an expedition equal to that of the genie belonging to Aladdin’s wonderful lamp.” (95)

The British tried to attack, but were turned back by a furious storm of snow and sleet. The storm gave them time to rationally assess their dire situation. Attacking the well-fortified Americans would likely be suicidal. But remaining in Boston would make them sitting ducks. Their cannonballs couldn’t reach the top of the hill. And their ships couldn’t risk staying in the harbor. The weather eventually calmed, but the Redcoats’ calm complacency was replaced by panic.  Their only choice was to tuck tail and sail, giving the American army extremely needed confidence that they could eventually defeat the British. (99-105)

The Attack on Trenton, December 26th, 1776

The British didn’t take this humiliating defeat lightly. Washington and his 9,000 troops next tried to fortify New York City, but the British showed up in force – massive force. In August, a breathtaking British armada of 400 ships appeared in the harbor, delivering 32,000 troops to Staten Island. (148, 158,161,191,197) It was “the largest expeditionary force of the eighteenth century, the largest, most powerful force ever sent forth from Britain or any nation.” (148)

Outmanned and outgunned, Washington decided that wisdom was the better part of valor. As the British advanced, he and his 9,000 troops cleverly snuck out of town under the cover of night, so that the British woke up to find, to their dismay, that their enemy had vanished. The British pursued the retreating army, which was growing weaker and weaker.  Thirty to forty soldiers at a time were defecting to the British.  Many of the remaining soldiers had no shoes. (225,254,269) Even some of Washington’s leaders began to question his leadership. General Charles Lee, Washington’s second in command, led the largest portion of Washington’s troops and was considered by the British to be the only respectable military leader in the entire American army. Many considered him America’s only hope. Their hopes were dashed when Lee was captured in a British raid. (51, 236, 264-266)

To many, it looked like all was lost. As the American army retreated further north, even the American Congress fled Philadelphia. Two former members of Congress defected to the enemy. (270) On December 1, with the British army two hours from them, two thousand American soldiers deserted the army and returned home – their enlistment was up. (256) 

With less than 3,000 men left, Washington retreated across the Delaware River. “The hour had never looked darker.” (257) Thousands of New Jersey residents traveled to the British camps to declare their loyalty to the King, so that their property and businesses would remain intact after British rule was reinstated. (258) “By all reasonable signs, the war was over and the Americans had lost.” (270)

Considering the state of the American army, the British once again swelled with overconfidence. As Lord Rawdon wrote, “their army is broken all to pieces, and the spirit of their leaders and their abettors is all broken…. I think one may venture to pronounce that it is well nigh over with them.” (251) A Loyalist newspaper in New York described the American army as “the most pitiable collection of ragged, dispirited mortals that ever pretended to the name of an army….” (260, 261)

But instead of attacking and ending the war then and there, General Howe decided to return to New York until spring, since cold weather had set in and he saw no reason to subject his troops to a harsh winter campaign. Considering the rebel army to be pitifully defenseless, he saw no harm in waiting until spring to crush them. That one act of underestimating the American army may have ultimately lost the war for the British. (276)

While General Howe vacationed in New York, leaving forces in Trenton and other outposts in New Jersey to hold the ground they’d taken, Washington kept learning. He wrote,

“Use every possible means without regard to expense to come with certainty at the enemy’s strength, situation, and movements – without which we wander in a wilderness of uncertainties.” (268)

Once Washington learned that many of the Redcoats were wintering in New York, he planned a daring raid on the holding army across the river in Trenton. Christmas night, during a blinding, vicious snowstorm (two of his men froze to death on the march) Washington and his troops crossed the river to mount a surprise attack.

The learned British leaders were put in jeapordy because of their smug overconfidence. General James Grant, the commander of the British holding forces in New Jersey, was confident that the troops in Trenton were as safe as if they were wintering in London. (284) Johann Rall, the senior officer who defended Trenton, completely underestimated the American army, holding them in contempt. (279) Thus, although Rall received two Christmas day warnings that the rebels were planning an attack on Trenton, he failed to take them seriously. (279)

By the time the Americans arrived, at just before 8:00 AM, their gunpowder was so wet that it was fairly useless. Largely with bayonets and hand-to-hand combat, they swarmed on the unsuspecting town. Washington took Trenton in a mere 45 minutes, taking 900 prisoners and six pieces of artillery.  (280,281,283)

The news of the American victory spread rapidly and had a remarkable effect. (283, 290-293) Hope replaced despair, confidence replaced fear and dread – the rebels had boldly confronted the enemy and won a stunning victory. Although it would be another six and a half years before the war ended, the battle of Trenton was a decisive turning point. As one classic study of the American Revolution concluded,

“It may be doubted whether so small a number of men ever employed so short a space of time with greater and more lasting effects upon the history of the world.”

So never grow overconfident – the Achilles Heel of the British military – because of what you’ve already learned.  There’s always more to learn, and the person or business or army that embraces this will always have an advantage over the merely learned. Never stop learning. As someone wisely said,

“In times of profound change, the learners inherit the earth, while the learned find themselves beautifully equipped to deal with a world that no longer exists.”

Takeaways from the Battles at Boston and Trenton

1. Listen to ideas from everywhere. The British ignored advice and failed to seek new knowledge of their enemy. Washington listened to and acted upon Rufus’ idea of transportable fortifications, although he wasn’t a senior officer. He also listened to Knox’s wild plan to haul the guns and cannons from Upstate New York. As McCullough summarizes the latter:

“That such a scheme hatched by a junior officer in his twenties who had had no experience was transmitted so directly to the supreme commander, seriously considered, and acted upon, also marked an important difference between the civilian army of the Americans and that of the British. In an army where nearly everyone was new to the tasks of soldiering and fighting a war, almost anyone’s ideas deserved a hearing.” (60)

2. Don’t get overconfident, no matter how much experience and education you’ve had. There’s always more to learn.

3. Listen to wise counsel. Washington was eager to attack Boston, knowing that if they made no decisive move, their dropping morale just might end the war. But his superiors in Congress advised against this because of Boston being so well-fortified. Instead, they recommended occupying Dorchester Heights. Fortunately, Washington was humble enough to listen.   

4. Don’t underestimate your enemy or your competition. They may be smart in ways that you lack.


1. Why do you think the British were overconfident?

2. In what specific ways did their overconfidence lead to defeat?

3. In what ways did Washington and his army keep learning?

4. What does this statement mean? “In times of profound change, the learners inherit the earth, while the learned find themselves beautifully equipped to deal with a world that no longer exists.”

5. How can developing a habit of daily learning result in a more successful life?

6. If you’re running a business, how can continual learning help you outperform businesses that rest in their present knowledge?

7. How can we make learning more fun and attractive?

Ideas for Presentation

1. Video Clip: Consider showing the scene from Pirates of the Caribbean where the British fleet had arrived to fight the pirate ships. When I first saw the scene, I recall thinking, “The British never had that many ships. Welcome to Hollywood!” Then, when I read that over 400 British ships arrived to take over New York City, I wanted to go back and count the ships in the “Pirates” segment. Showing this might help students imagine the enormity of the British fleet that Washington saw as he and his soldiers gazed awestruck into the harbor.  

2. Use maps and pictures. Showing the hills of Dorchester and their proximity to Boston and the harbor can help students understand the strategic nature of Dorchester’s hills. Showing New York harbor, where the British troops landed on Staten Island, where they landed in New York City, where the Americans escaped from NYC, how close Trenton was to the command center (Congress) in Philadelphia, etc., adds to students’ understanding of these battles and why intelligence was so necessary.

Copyright December, 2011, by J. Steve Miller. See more character and life skills resources at . Feel free to use this with your students. Not for resale. Facts from David McCullough, 1776 (New York: Simon & Schuster, 2005).


The American Revolution: A Life Skills Lesson