With the Highlands secured, the countryside became relatively calm, yet not immune to British raids and interest. Bottled up in New York City, they still understood the vital strategic importance of the Hudson, but were unwilling to commit forces in an attempt to seize it again. Instead, they turned to subterfuge and treachery.

In Benedict Arnold they found a willing, if initially reluctant, conspirator.

Arnold's story is complex at it simplest. One of Washington's favorite and most trusted generals he enjoyed a closeness and intimacy of friendship few were privileged with. As a hero of the Battle of Saratoga, had he retired from the scene he would even now be remembered as one of the greatest commanders of the war. Because of the trust Washington placed in him, and because of the vital importance of the Hudson Highlands, Washington appointed him as the Commander of West Point and the fortifications and defense of the Hudson Highlands.

Exactly why he changed sides and became traitorous to the cause is not completely known. It is speculated that because he was passed over for promotion, he became bitter and despondent, allowing his mind to focus on the problems and imbalance of forces rather than the strategic superiority and long term advantages. For whatever the reason, he decided to place his and the colony's fate in the hands of the British, less than a days ride down the river.

To accomplish this, he determined to hand West Point and the defenses of the Hudson Highlands over to the British, for a bounty and certain considerations. Had he succeeded, we would be drinking tea now rather than coffee, that is how important the Hudson River was. Through a series of clandestine meetings, beginning early in 1779 and lasting over a year, he arranged to hand over the plans for West Point to the British, allowing them to send forces up the river and take control of the Hudson Highlands.

His negotiations broke down as the British looked to the south to combat a small French flotilla in Savannah. In May of 1780, Arnold reinitiated his contact informing the British that a French force under the command of General Rochambeau was on its way to Newport, Rhode Island. In response, British Admiral Clinton broke off his Southern campaign, left Cornwallis in charge and returned to New York to prepare for the French assault.

On the night of September 21, 1780 Andre met with Arnold and was given the plans to West Point.

It almost worked, except for two small things.

First, General Washington arrived unexpectedly on totally unrelated matters causing Arnold to panic thinking he had been discovered. In his panic, he fled reaching the British frigate Vulture surrendering himself to the commander. At the time Washington arrived, he had no knowledge of the treason

The second, and more important reason the plan ultimately failed, was that the British agent, Major John Andre, was noticed by a couple of country militiamen in Tarrytown. While he was meeting with Arnold the ship that had brought him up river, the Vulture, had been attacked by colonial forces in a totally unrelated engagement and withdrew up the river. Finding his means of escape gone, Andre had to adopt a disguise and was forced to travel cross-country behind enemy lines to reach British forces to the south. The letters and plans were discovered and he was taken prisoner and removed, via West Point, to Tappan. Andre's fate was to be tried and hanged as a spy.

Benedict Arnold

Born Norwich, Connecticut January 14, 1741. Arnold was an American Revolutionary general and America's most infamous traitor. At the age of 14, Arnold was a druggist's apprentice, but he ran away twice to serve in the colonial militia during the French and Indian War (1754-63). When the American Revolution broke out, Arnold marched his Connecticut militia company to Massachusetts, where he was made a colonel. His force, along with Ethan Allen's Green Mountain Boys, captured Ticonderoga on May 10, 1775.

He then led a force of 1,100 men through Maine in the dead of winter in a campaign to invade Canada, a march that a military classic. Linking up with another American force under Richard Montgomery, he led an unsuccessful attack on Quebec in December and was wounded. For his courage, he was promoted to brigadier general in January 1776.

Before his defection, Arnold had a brilliant career in the Continental Army. In October 1776 he fought a series of naval battles on Lake Champlain helping to delay a British invasion south from Canada. In April 1777 when the British raided Danbury, Connecticut he drove them off. Arnold particularly distinguished himself in the Saratoga campaign as second in command to Horatio Gates. During the second battle of Saratoga on Oct. 7, 1777, Arnold led a headlong charge, captured a key redoubt, was again wounded, and made the British surrender inevitable. Disobeying the orders of General Horatio Gates and without any regard for his own safety, he almost single-handedly rallied the Americans to victory at Saratoga. One of his soldiers called Arnold "as brave a man as ever lived."

Arnold suffered many disappointments that plagued his mind and embittered him. When he was promoted to major general in February 1777, others he thought less deserving preceded him in rank. Gates received the credit for the victory at Saratoga. Named commander in Philadelphia, Arnold was accused of overstepping his authority. His second marriage to Margaret Shippen, the daughter of a Loyalist, also aroused suspicions.

His bitterness, along with a need for money to pay heavy debts are probably the personal reasons that led him to negotiate with the British. He conceived a plan to betray West Point, a post that he commanded.

When Benedict Arnold wrote this letter to John André, he was still in Philadelphia. General George Washington had agreed to let Arnold have command of West Point on June 29, 1780. Arnold’s command included not only West Point but also the area from Fishskill to King’s Ferry, the infantry and cavalry on the east side of the river down to British lines, and the forts at Stoney Point and Verplanck’s Point. Arnold probably did not leave Philadelphia for West Point until after July 21. Nevertheless, in this letter Arnold offered to surrender West Point for 20,000 pounds. Because of delays in communication, Arnold did not know that his offer to surrender West Point had been accepted until August 24, 1780.

Throughout this time, Arnold’s post at West Point was not yet guaranteed. Arnold met Washington on July 31 as Washington was crossing the Hudson at King’s Ferry, and Washington suggested that Arnold take command of light troops in a campaign against the British in New York. Remember that over a month earlier, Arnold had betrayed Washington’s movements and his plans with the French. Perhaps in response to Arnold’s intelligence, Sir Henry Clinton decided to stay in New York to defend that area from a French advance as well as to prevent General Washington’s troops from crossing the Hudson River to meet up with the French troops. The French Comte de Rochambeau’s troops landed on July 12, 1780, and Washington crossed the Hudson at King’s Ferry on July 31, 1780 to meet them. A few days after Washington suggested that Arnold help him in his advance towards Clinton’s troops, Arnold pleaded that his wounded leg prevented him from taking the field. So Washington allowed him to take command of West Point on August 3 instead.

West Point was valuable because of its strategic position. West Point was poised at a sharp curve in the Hudson River. At West Point, it was possible to lay defenses in the Hudson River that would prevent any ships from navigating it. Possession of West Point would have enabled Clinton to gain control of the Hudson River and divide the colonies. Furthermore, at this point in time, if Arnold would have surrendered West Point, Washington would have had to retreat from his current position in New York, break off his plans to unite with the French to attack Clinton in New York, and leave French troops vulnerable in Long Island. Clinton then could have defeated the French.

Although Arnold had repeatedly sent Clinton letters through his intermediaries throughout July, apparently Clinton did not receive any of them. In a letter that Arnold received on July 13, 1780, Clinton had responded to Arnold, through André, but did not acknowledge any of the information that Arnold had sent previously. Clinton even asked Arnold to continue to send Clinton more regular information. In response, Arnold fired of this letter about his terms of service. In this letter, he made reference to the previous letter, to which he mistakenly referred as written on July 13 instead of on July 12, and told Clinton that he had already supplied intelligence. Arnold had previously thought that his messengers (Jonathan Odell and Joseph Stansbury) were untrustworthy and later began to use Samuel Wallis instead of Stansbury as his agent, but Clinton may not have seen his letters because he was preoccupied with capturing Charleston, South Carolina and preparing for the French to arrive in Newport, Rhode Island.

After Arnold assumed command of West Point, he continued to correspond with André. To prepare for the surrender of West Point, Arnold scattered his troops to weaken West Point’s defenses. On September 19, Clinton readied his men and ships to capture West Point as soon as André had finished the final negotiations with Arnold. But on September 23, 1780, the Americans captured André while he was carrying papers relating to West Point’s garrisons and defenses and a pass from Arnold. Thus, the plan failed and Arnold’s treachery was revealed.

His attempted treachery was revealed when John Andre, a British major, was captured carrying Arnold's message. Arnold escaped to the enemy lines and was commissioned a brigadier general in the British army. For his property losses, he claimed and was paid about $10,000. He led two British expeditions, one that burned Richmond, Va., and the other against New London, Connecticut.

Arnold went to England in 1781 and turned to trade. Worn by depression and suffering from a nervous disease, he died in London on June 14, 1801.

Major John Andre

In April 1779 John André was placed in charge of the British Secret Intelligence. In this role he lead the negotiations with Benedict Arnold, which had been in progress since 1778. As Arnold was promoted to commander of West Point in August 1780, the British began to take his offerings seriously.

All that remained were the final details. Not easy to arrange, Arnold demanded a personal meeting with André. He asked André to go to Sheldon's Headquarters at Lower Salem, disguised as "John Anderson," an American agent. This would expose André to all of the hazards of ordinary secret agents. If André was disguised to look like a spy, he would be captured as a spy. Clinton and André did not want this to happen. André wanted the final meeting to be in public, so that he would not have to take any unnecessary risk. However, as time wore on and they were unable to make these plans, Clinton and André agreed to follow Arnold's lead.

On September 20th, André went on board the Vulture, a British sloop in the Hudson off Teller's Point, to await for an American ship to pick him up and take him to Sheldon's Headquarters. It was not until the night of the 21st, that André was picked up by Joshua Smith and taken to meet with Arnold. André wore his uniform so that he would not be taken for a spy.

Arnold met André on the shore near Haverstraw, NY and they went back to Smith's house, behind American lines, to talk. There, Arnold gave André papers of West Point, which revealed the placement of troops and other compromising information. By morning the meeting was over, but the Vulture had moved up river, having been fired upon by the Americans. This stranded André.

As a result of the Vultures move, André was forced to go back to the British by land, something he was loath to do, knowing of the dangers. To help out, Arnold wrote some passes, using the disguised name of "John Anderson," for André to get back to safety. André was not happy with these circumstances, and when it was decided that Smith would help lead André toward the British, André began to see himself as a prisoner and decided it was best for him to change out of his uniform and be disguised for the trip. André wanted to move fast and go all night, but on the 22nd , they ran into some New York militia men who convinced them to stay the night with them and move on in the morning.

André could not give up his disguise, because all of his negotiations had been in secret. If anyone in the countryside had realized he was British they would have reported him. Therefore, he had to relent for the evening. On September 23rd, Smith finally left André's side near Pine's bridge, over the Croton River. They both believed that André would not see any more Americans past this point and that he would safely make it to the British lines. Around 9 am that morning though, he was stopped in neutral territory, near Tarrytown, by some militia men. We do not know exactly what happened in this encounter because of conflicting stories, but André is recorded as having said, "I was taken by three volunteers who, not satisfied with my pass, rifled me and, finding papers, made me a prisoner". He may have thought the men to be loyalists at first and then realized his mistake too late.

The men, finding the papers from Arnold on him, took André to North Castle, where Lt. Col. Jameson was in command. Jameson, not sure what to do, first sent a letter onto Arnold, his commander, concerning the situation. At this point Benjamin Tallmadge returned to North Castle from scouting and, being very suspicious of these goings-on, sent a letter with the found papers to Washington . André was held prisoner. Meanwhile, Arnold received the letter, and just missing having breakfast with Washington, who had not gotten his letter yet, fled for the Vulture and British safety.

Arnold escaped, but André was to be tried as a spy. Something he had wanted to avoid from the very beginning. When Washington read the letter, he asked for the Court of Inquiry to study the incident and decide whether André was acting as a spy. The British believed that the Americans would not dare to execute a British Adjunct General. There was a trust between sides that generals would be taken as prisoners and not executed.

André was moved from Headquarters, to West Point, and finally to Tappan, where he was housed in a tavern. There, as the verdict was decided that André was acting as a spy by going behind enemy lines and disguising his uniform, he wrote a courageous letter, dated September 29, 1780, to his Commander, General Henry Clinton. All the men on both sides were amazed at the turn of events. The American men admired André for his gallantry as much as the British did for his leadership. No one wanted him to die, but Washington had to be firm and did not back down. André was hanged as a spy at Tappan, New York, on Oct. 2, 1780. He was mourned even by his enemies.

André was an important general to the British and the loss of him was felt strongly. Everyone believed that Arnold should have been the one to die because of his treason and that André just happened to be in the wrong place at the wrong time. The Americans wanted to trade, but the British would not do it, knowing what would happen to Arnold.

"Last Moments of Major Andre"