Confederate Lt. John T. Wood was already considered a distinguished navy man early in the war, but with his midnight raids on Union ships he truly won distinction and earned a reputation as a swashbuckling coastal raider. His first strike, on the Union schooner Frances Elmore on October 7, 1862, marked the beginning of Wood's escapades. Most often, Wood used cutting-out expeditions, in which cutters were hauled overland by wagons and then launched in streams in the middle of the night. Fifteen to 20 men in each cutter would row up to an enemy boat, overpower her crew "with blazing revolvers and slashing cutlasses," then sail away in the vessel. Eventually even the mention of Wood's name was enough to strike terror into the hearts of Union boat commanders.

In July 1863, with Union gunboats in the Chesapeake Bay prohibiting blockade running, Wood ambitiously decided to capture two gunboats with his four cutters. On August 22, under a stormy night sky, Wood led his 80 men down the Rappahannock to the bay, where their prey lay waiting.

Wearing white armbands to help them distinguish friend from foe, Wood's men rowed to within 50 yards of the first ship before being sighted. At that point, one of Wood's men recalled, "Every man put his whole strength to the oars. Our boat nearly sprang out of the water at every stroke, and shot over the waves with the velocity of an arrow. In a few seconds the dark hull rose before us...and, as quick as thought, twenty of us were climbing over the nettings upon her decks." In less than 10 minutes, Wood and his men had secured the first ship; soon thereafter, they had the second gunboat. Wood's prowl continued, and in two days he netted three more vessels.

In February 1864, during a raid on New Bern, North Carolina, Wood captured the gunboat Underwriter. In August of that year, Wood was given command of the CSS Tallahassee, on which he terrorized the North, from New York to Maine, capturing or destroying 31 Union vessels before his raiding career was through.

In his Chesapeake bay raids, Wood shocked the North, embarrassed the Union flotilla, and seized valuable equipment for the ailing Confederate navy--all without losing a single Rebel.

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