On Tuesday, February 9, 1864, 109 federal officers held in Libby Prison in Richmond, Virginia escaped after 17 days of laboriously tunneling their way out of prison.
Included among the escapees was Union General A.D. Streight, who led a successful cavalry raid from Alabama into Tennessee in April and May of 1863 but had been captured. So effective was the escape, the Confederate guards did not realize there was a problem until after the morning roll call of prisoners.
By then, twelve hours had lapsed, giving the escapees valuable time to get away. In this, the most sensational and largest prison break of the American Civil War, eventually 59—including Streight—reached Federal lines. Forty-eight escapees were eventually recaptured, while two unfortunately drown in the James River.this