An 1841 graduate of the US Military Academy at West Point, NY, he was born in Greenwich, Massachusetts. His first assignments took him across the country among them was determining the route of the transcontinental railroad. His mapping skills and talent were key in the US Civil War when he served as chief topographical engineer with the Army of the Potomac under General George B. McClellan. Later he would command the defenses of Washington using the Custis-Lee mansion - Arlington House - as his headquarters. During that time he befriended President Abraham Lincoln who would drive over from Washington DC to meet with General Whipple, often having lunch and getting a briefing from the General while Lincoln wrapped his arms around Whipple's two sons. General Whipple wanted a combat role and commanded a division at the battles of Fredericksburg and later Chancellorsville. It would be there that a sharpshooter would shoot him while he was mounted on his horse. He would be taken back to Washington DC where on May 7, 1863 would succumb from his wound. Later Abraham Lincoln would attend his funeral, not as the President but a friend. In the book "Images of America - Fort Myer"the closeness of these two men is shown in an unpublished note from President Lincoln to General Totten which nominated General Whipple's son to West Point. General Whipple would later be honored when a fort was placed where he ordered an observation balloon sent up to observe combat activity to the west. Fort Whipple would ultimately evolve and grow in use and importance after the Civil War and become Fort Myer.