Thomas Leslie Outerbridge (died 5 September 1927) was a notable Bermudian, who participated in the American Civil War as a sailor aboard blockade runner ships from Bermuda.

Involvement in the American Civil War

During the War, the Union imposed a blockade on the Confederacy, which was then an important trade partner with European countries, particularly England. Harbours such as Bermuda's St. George harbour and Nassau in the Bahamas became important bases for blockade running missions. Such missions became exceedingly dangerous; blockade runners were paid far greater sums than ordinary sailors. Outerbridge and his brother both took this opportunity.

Thomas Leslie Outerbridge

On one occasion, Outerbridge was serving aboard the steamboat Robert E. Lee. Departing from Wilmington at about 9 p.m. (at high tide, which is when the large ship could get over Wilmington's sandbar), the Robert E. Lee joined a small fleet of blockade runners which was soon attacked by two Man-of-War ships, flanking the fleet on either side. The Man-of-Wars immediately attacked with heavy cannons, destroying a winch and severely wounding a number of foreign sailors. One of them approached the Robert E. Lee close enough for small arms fire, though there were no casualties.

Thomas Leslie Outerbridge

While the captain, Wilkinson, studiously ignored the attack, Outerbridge, the mate and a number of crewmen had gone to the forecastle to watch for other craft. A round shot hit close to Outerbridge, causing him to fall unconscious while the other crewmen fled. The following day, Outerbridge was commended by the ship's officers for his bravery, and the crew picked small bullets from the woodwork.

Thomas Leslie Outerbridge

At the time, the Robert E. Lee was en route to Halifax with a number of Confederate officers on board. The Confederates were bound for England to collect two Man-of-Wars for the Confederate government (the Viper and the Vixen). The British government seized the officers and sent them to Bermuda. The Robert E. Lee also set course for the island.

Not all of Outerbridge's adventures in the Civil War would be as pleasant, as he would be twice captured by the North. On one of these occasions, he was serving on the steamer Sirene. Originally owned by the British government and used as the Dockyard duty boat, the ship was mothballed and sold to Mr. Fininsey, the popular Confederate Consul in Bermuda. Fininsey deployed the Sirene to Wilmington with a crew to bring back another steamship, the Cape of Good Hope, to act as a cotton freighter. At the time, the Cape of Good Hope was a passenger boat between Wilmington and Smithfield, a role that the Sirene would then fulfill. Captain Jeremiah Peniston was selected as the ship's Master, with Outerbridge's brother Eldon Outerbridge as first officer and Outerbridge himself as second officer. A Virginian man by the name of Mr. Tab was the ship's purser.

A week out of Bermuda, the rather slow Sirene reached the American coastline off Bowford, North Carolina. They headed southward towards Cape Fear under sail, hoping that it would deceive the blockade fleet. Only an hour later, the Man-of-War Key Stone State (which was later purchased by a Mr. Webb of New York, renamed the San Francisco and used as a mail ship to Bermuda) intercepted the Sirene and towed it into Bowford, with the crew laughing at the blockade runners' pitiful craft.

The following day, the crew were transferred onto a receiving ship in Bowford's harbour, where they found a welcoming presence in the ship's captain. Having visited Bermuda several times in a whaler, the ship's captain was kind towards his prisoners. However, they spent the next ten days treated like fighting cocks. Four days into this, the Sirene crew witnessed another blockade running steamer, the Pavince, being chased on shore by the Man-of-War. The steamer was fast enough that the crew had the leeway to abandon the ship and row ashore on small craft, but they were immediately captured by Union soldiers. The Pavince was at that time on fire, and exploded. With the crew of the Pavince – also familiar with the Captain from his time in Bermuda – aboard, the blockade runners "had a good time as long as [they] were there".

After the ten days, the blockade runners disembarked into Camp Hamilton, which was under military authority. Treatment was severe. Four days into the stay, the Union wardens sent all imprisoned masons – including the both blockade runner captains and some fifteen thousand Confederate soldiers.