On October 19, 1864, twenty-one Confederate soldiers led by Lieutenant Bennett H. Young launched a surprise raid on the quiet town of St. Albans, Vermont.
Intending to plunder funds for the struggling Confederacy and force the Union to divert troops to its northern border, the covert raiders held three local banks at gunpoint. They made off with over $200,000 in U. S.
currency—a massive fortune at the time. Their escape strategy relied on fleeing across the nearby border into neutral British Canada, where Union forces could not legally pursue them. However, their victory turned into a financial disaster.
Upon arriving in Montreal, the raiders attempted to convert their looted haul into gold or British pounds to purchase military supplies for the South. They immediately ran into an insurmountable wall. Canadian financial institutions were deeply wary of the sudden influx of massive, unverified American bank notes.
Furthermore, Canadian authorities quickly arrested the raiders to maintain neutrality. In a surreal legal twist, a Montreal magistrate released $88,000 of the seized cash back to the raiders on a jurisdictional technicality, provoking international fury from Washington. Yet despite holding thousands in cash, the raiders found that wartime inflation, exchange rate crashes, and international legal impoundments rendered the stolen greenbacks effectively unconvertible and worthless for funding the Confederate war effort.