In October 1864, a group of Confederate agents based in Canada orchestrated a daring bank robbery in Saint Albans, Vermont, targeting three banks. Led by Captain Bennett H. Young, the agents strategically planned the heist to coincide with a critical period of the Civil War, one where the Confederacy was struggling with dwindling resources. On that fateful day, the group, equipped and motivated, stormed into the banks, demanding cash and valuables from the stunned employees and patrons. Their meticulous planning allowed them to steal an estimated $200,000, a considerable sum at the time, equivalent to millions today.

The robbery not only aimed to secure funds for the Confederate cause but also sought to instill fear and demonstrate that the war was affecting even remote locations in the Union. Following the heist, the agents made their getaway, but they were pursued by law enforcement led by U.S. Marshal Allan Pinkerton. Despite the manhunt, Young and his men managed to evade capture, crossing back into Canada where they would remain elusive from Union forces.

The incident exemplified the desperation of the Confederate agents as they looked for any means to fund their struggle against the Union. It highlighted the porous border between Canada and the U.S., allowing Confederate sympathizers to launch operations from Canadian soil. The Saint Albans raid became one of the most audacious acts of the war, garnering substantial media attention and serving as a reminder that the conflict had many facets, including financial warfare.