Element of Surprise
The tunnelers organized into three relief teams with five members each. After 17 days of digging, they succeeded in breaking through to a 50-foot vacant lot on the eastern side of the prison, resurfacing beneath a tobacco shed inside the grounds of the nearby Kerr's Warehouse. When Col. Rose finally broke through to the other side, he told his men that the “Underground Railroad to God’s Country was open!” The officers escaped the prison in groups of two and three on the night of February 9, 1864. Once within the tobacco shed, the men collected inside the walled warehouse yard and simply strolled out the front gate.
Union officers meandering through the streets of Richmond late at night might appear to be a leg of the plan doomed to failure, however, the guards simply did not expect that escape from Libby prison was possible. The fact that the Libby guards were not looking for signs of escape meant that they were in a position to be more easily deceived. Union Army Lieutenant Moran described how the sentries were not interested in stopping people outside the bounds of their jurisdiction, "provided, of course, that the retreating form...were not recognized as Yankees." The tunnel provided enough distance from the prison to stealthily subvert those jurisdictional lines and allow prisoners to slip into the dark streets unchallenged.
So effective was this buffer that 109 men escaped the prison without ever being stopped. At one point, Colonel Rose walked straight into the path of an oncoming sentinel. Unflinching, he "strode boldly past the guard unchallenged." Even more amazing, once news of the escape way broke out among the prisoners a panicked rush resulted, creating a thunderous stampede for the tunnel. Wholly unsuspecting of the reality of the situation, one Confederate guard yelled out to a fellow sentry, "Halloa, Bill—there’s somebody’s coffeepot upset, sure!"
Read more about this topic: Libby Prison Escape
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