What if Jeremiah Greenman’s leader had behaved differently?

Benedict Arnold was the leader of the Quebec march. He was Greenman’s leader. Surprised? Get ready for more surprises. Before we go to the “what-if”, permit me to provide some background.

Benedict Arnold is the most infamous traitor in American history. His name has become a synonym for betrayal and has remained thus for more than 200 years. That’s a legacy.

Arnold was 34 years old at the time he was Greenman’s leader. Born in Norwich, Connecticut, Arnold had grown up in a commercial seafaring family. The family business had collapsed because of Arnold’s alcoholic father. Young Arnold was forced to withdraw from school at age 14. He became an apprentice to a druggist and trader.

Arnold started his own trading business at a young age before the start of the Revolutionary War. He became successful. Under his guidance, ships carried various goods between New England and the West Indies. He spent a lot of time on business issues. Dark-eyed, a tanned hue to his skin tone, and with a powerful, compact build, Arnold was energetic, ambitious, and hard-working.

He joined the American cause immediately after the war started in April 1775, six months before the Quebec assignment. He became a military officer and within weeks displayed a combination of raw courage, risk-taking, and passion that he didn’t try to conceal. Soldiers like Greenman were drawn to him.

Arnold was one of the leaders of a military expedition that captured and secured Fort Ticonderoga in northern New York during spring 1775. His skills as a leader were evident during the mission. His flaws were similarly visible—hot-tempered, rash, unforgiving. Somewhere in between skill and flaw were other leadership qualities of Arnold. They included a strong self-belief in his own vision and analysis and a willingness to tackle challenges (including rivals) head-on. The mix of white, black, and gray is common to all of us.

Arnold was General George Washington’s choice to lead the Quebec expedition. The purpose was to make Canada (a British colony recently acquired from France) into the 14th rebellious American colony (later, state). Arnold’s expedition was part of a two-pronged effort, the other led by Richard Montgomery and driving toward Quebec from the southwest, through Montreal.

The expedition to Quebec failed miserably. Arnold was wounded in the leg. He and Montgomery had over 900 men with them but lost almost two-thirds in the assault on Quebec and its aftermath.

Arnold went on to become the most talented field combat leader in the American army. He was the key leader in several military operations, including on Lake Champlain in 1776 and at Saratoga, New York in 1777, where he received his second severe battle wound. This wound ultimately resulted in his left leg being two inches shorter than his right. By this time he had risen to the rank of general, albeit with considerable friction between himself and fellow officers.

The alliance between the United States and France, announced in 1778, was bitterly opposed by Arnold. Arnold despised French culture, French people, and French institutions. The Franco-American alliance (later credited by historians as a vital reason why the US won the Revolutionary War) began Arnold’s slide into treason. Subsequently, he wrote public documents which attributed his treason to the French alliance.

Another reason was family. Arnold married 18-year-old Peggy Shippen in 1779. Shippen’s family was staunchly pro-British, opposed to the formation of a new United States. Moreover, the Shippens were wealthy and young Peggy expected such wealth to continue to define her life. Benedict Arnold plunged deeply into debt, plunged deeply into the personal networks and relationships of the British-sympathizing Shippens, and plunged deeply into a desire to right the wrongs he thought had been done to him in recent months.

Those perceived wrongs were rank, titles, and in a word, power. Arnold believed other officers had been promoted at his expense. He believed that the American Congress didn’t appreciate his efforts and sacrifices. He demanded satisfaction.

Through it all, Arnold had emerged as one of George Washington’s most trusted generals. Washington understood Arnold’s flaws but he valued his strengths, especially as a leader on the battlefield.

By 1780 Arnold began a secret correspondence with British officers, primarily commanding British General Henry Clinton. Arnold became the American commander of West Point, a fort on the Hudson River. West Point was seen as vital to American strategy—hold the fort and the US controls the river, lose the fort and the young nation would be split in half and lie prone to British military domination.

It was this fort that Arnold offered to hand over to the British in exchange for money and higher military rank in the British Army. His plans collapsed when a British secret agent was captured on September 23, 1780. Arnold escaped to a nearby British ship, aptly named the Vulture.

Washington had scheduled a meeting with Arnold on that day. Washington and three of his aides were left waiting for Arnold, unaware that Arnold had escaped to the Vulture. Peggy Arnold was still in her husband’s quarters at West Point. She pretended to lapse into a fit of lunacy to distract Washington while her husband made his get-away.

Arnold joined the British Army. He led two military expeditions against his former country, one in Virginia and another in his home state of Connecticut. He killed, raided, burned. Within months, Arnold fell into disputes with fellow British officers. Arnold left the US for England in 1781 and became a military advisor to King George III. He died in 1801 in London. Today, Arnold’s former house in London has a plaque which reads: “American Patriot.”

Arnold presents us with two “what-ifs.”

The first is what if Arnold hadn’t betrayed his country? Clearly, he was skilled as a battlefield commander. It’s almost certain that Arnold would have been remembered and revered as one of the founding spirits of the American military—bold, resourceful, courageous—and hallowed by subsequent generations of US soldiers. He would have secured as exalted a place as George Washington in the hearts and minds of American military culture.

Furthermore, Arnold would likely have found a way to re-enter combat leadership. Despite two severe wounds, despite one leg two inches shorter than the other, Arnold would have succeeded in staggering back onto the battlefield. It’s likely that he would have won combat victories.

From that point, anything would have been possible for Arnold. As the 1780s unfolded, based on his military exploits, Arnold would have secured some sort of involvement in either the Constitutional Convention of 1787 or the state ratification convention in Connecticut in 1787-1788. A state political office would probably have resulted. All of this would have been in conjunction with his substantial business activities. There would have been problems, to be sure—his personality and that of his wife would have seen to that—but Arnold’s post-war life undoubtedly would have been vastly different if he had not betrayed his country.

The second what-if is this: what if Arnold had succeeded in his betrayal and given West Point to the British?

No place was crucial to American victory. Not Boston, not Philadelphia, not New York or Charleston or any other physical location—except for one. The American cause would have survived the loss of West Point. The war might have been prolonged. Arnold’s reputation within the British Army might have been boosted, if only for a short time. But that’s it.

Now, let’s go back to my phrase above: “…except for one.” There was one place in the thirteen US states at that time where the American cause could not afford a loss. One place. That place was this—wherever George Washington was. If Washington had been captured, the war was lost, not immediately, but certainly lost at some point soon arriving.

This is the intriguing element of this second what-if. What if Arnold’s treason had succeeded on September 23, 1780, the day Washington had set for a meeting? What if the British effort to grab a key American fort had also resulted in grabbing the central American leader of the rebellion? The effect would have been devastating to the American cause.

To my knowledge, Arnold had not planned to hand Washington over to the British. He only planned to give up the fort. Indeed, his decision to flee to the Vulture was based on the collapse of his scheme. It was pure chance that his commanding general had scheduled a meeting at West Point on the same day.

And now a third what-if occurs to me. What if Washington succeeded in capturing Arnold after his betrayal? The effect of Arnold’s treason on American morale was substantial. Public opinion reflected a dive in support for the American cause. Washington referred to it as one of the darkest times of the war. To stanch the bleeding, Washington pledged to capture Arnold. He made it one of the top military priorities in 1780-1781, including organizing covert operations to pull it off.

If Washington had captured Arnold, I believe there would have been a swift trial in the form of a special court martial. I believe further that the verdict would have been rendered in a matter of hours. Arnold would have been hanged. It would have become one of the most searing images of the entire war, of the entire American Revolution. Quite likely, the legacy of the American Revolution would have a bloodier stain.