4. Southern Maryland was a hotbed of Confederate sympathizers and agents
Maryland had been a slave state before the war, and though it did not secede and join the Confederate States, its population was divided over support of the Union. Southern Maryland, through which Booth and Herold fled, was an area which both knew well, and which contained a large number of anti-Union activists. Throughout the war Confederate agents and spies operated in the area, infiltrating Washington and sending reports of Union activity to handlers in Richmond, and to the headquarters of the Army of Northern Virginia. Herold hoped to connect with sympathizers to help whisk them south to Virginia and safety.
As yet unknown to Booth and Herold was that the Secretary of War had authorized the largest reward in the nation’s history up to that time for the capture of John Wilkes Booth – $100,000 (equivalent to $1.6 million today). Booth’s conspiracy unraveled rapidly. By the morning of April 15, the day Lincoln died, Stanton was aware Booth had fled into Maryland, and the region was flooded with Federal troops. Booth, had expected a hero’s welcome after killing Lincoln, instead, he was forced to hide in a swamp, in a dense pine woods, literally gone to ground, while Herold attempted to solicit help crossing the Potomac into Virginia.