Andre started his military career at the age of 20 as a lieutenant and within a few short years he reached the rank of Major. In April 1779, he was placed in charge of the British Secret Intelligence. By the next year he had begun a correspondence with American General Benedict Arnold through his loyalist wife, Peggy Shippen. It is said that Andre courted Shippen in Philadelphia prior to her marriage to Arnold. On September 20, 1780 Andre went to visit Arnold at West Point in New York to discuss its surrender to the British for £20,000. In addition, Arnold would receive the rank and recognition he felt he deserved, but this time as a British Officer. Morning came before they had finished talking, and Andre could not make it back to the ship the Vulture. André was then given civilian clothes, a passport signed by Arnold and papers showing the British details of the fort. André hid these items in his boot. Since Andre was not in uniform and claiming to be a John Anderson when he was captured the Americans treated him as a spy. André testified at his trial that the men searched his boots for the purpose of robbing him. General George Washington was on the board of senior officers to investigate the matter. On September 29, 1780, the board found André guilty of being behind American lines "under a feigned name and in a disguised habit", and that "Major André, Adjutant-General to the British army, ought to be considered as a Spy from the enemy, and that agreeable to the law and usage of nations, it is their opinion, he ought to suffer death." Sir Henry Clinton, the British commander in New York, did all he could to save his favorite aide, but Andre was to be hanged as a spy at Tappan on October 2, 1780.

                                                               Alexander Hamilton