At the beginning of the Civil War, Allan Pinkerton, founder of a detective agency, gathered intelligence for George B. McClellan, a Union General. In addition, Abraham Lincoln had Pinkerton take charge of intelligence for his Army of the Potomac. In 1861, Pinkerton set up the first union espionage operation. Pinkerton built a counterintelligence network in Washington, sending agents to Richmond, the competitive capital. However, in 1862, during the Peninsula Campaign Pinkerton’s intelligence reports were often wrong, resulting in unnecessary Union moves like calling for reinforcements or waiting to attack. At the time, Union espionage was decentralized, meaning there was no central network of spies. Rather, generals like George McClellan and even President Abraham Lincoln used spies to collect information that would help them predict enemy moves.
Generals Grenville M. Dodge and Ulysses S. Grant created a powerful secret service operation that they could rely on for military and political intelligence, aiding them throughout the war.
Pauline Cushman, who was an actress before the Civil War, became a spy for the Union. While on tour with her theater troupe, by praising the Confederacy in a staged toast, Cushman connected with Confederate officers and was able to steal battle plans and hide them in her shoes, delivering them to Union officers. Although she was caught and sentenced to hanging, she was later saved by a Union attack. In 1865, she gave lectures on her work as a Union spy.
Harriet Tubman, formerly enslaved, became a Union Spymaster during the Civil War. Tubman was recruited to build a spy network consisting of former slaves in South Carolina. Prior to becoming a spy, she had also volunteered as a cook and a nurse for the Union. In addition, she was a prominent conductor of the Underground Railroad, helping to lead over 300 people to freedom. Harriet Tubman also became the first woman in US history to lead a military expedition. She helped Colonel James Montgomery plan a night raid to set free enslaved people. On June 1st, 1863 Tubman and Montgomery traveled on the Combahee River, avoiding remote landmines, and eventually reached the shore of a Confederate rice plantation where they destroyed Confederate supplies and freed more than 750 enslaved people.
Mary Elizabeth Bowser, also known as Mary Jane Richards, was an enslaved woman who was freed after her enslaver Jon Van Lew passed. His wife and daughter were opposed to slavery and secretly freed Bowser. Elizabeth Van Lew helped imprisoned Union soldiers escape by conveying messages between prisoners and Union officials. To pass on these messages Van Lew relied on a network of people that were a part of Richmond’s Union community. One of the most important individuals that took part in his network was Mary Bowser. Bowser also once infiltrated the Confederate White House, putting her life on the line to gain valuable information that would help the Union win the war.