Confederates Lost at Sea

The visual landscape of the Civil War is drawn from Mathew Brady’s photographs of mangled corpses, sepia portraits of a troubled Lincoln, and images of the spindly ruins of Atlanta and Charleston. The war hardly conjures the listing masts of burning whaling ships in the Arctic night, or the silhouette of a stealthy steamer nosing between icebergs. But long after the surrender at Appomattox, a Confederate raider was dogging ships from the Union, believing her cause was still alive.

With the North’s naval blockade strangling its ports, the Confederacy sent a dozen or so men-of-war into the world’s oceans to harass unarmed Yankee vessels and upset the Northern economy. These raiders skated a thin line between privateering and piracy. The CSS Shenandoah, commanded by Captain James Waddell, sank 32 Union merchant and whaling ships, making her the third most successful Confederate raider, and she was the only one to circumnavigate the globe.

“Just as war will have its heroes and its tragedies, so, inevitably, will it have its ironies. That the task of firing the final shot associated with that entire four-year ordeal of death and destruction fell to Waddell and the men of his Shenandoah was surely one of them,” writes Tom Chaffin in his meticulously researched new book on the warship’s amazing journey, Sea of Gray: The Around-the-World Odyssey of the Confederate Raider Shenandoah (Hill and Wang, $25). Chaffin, the author of Pathfinder: John Charles Frémont and the Course of American Empire, has drawn from a rich array of primary sources, including shipboard journals, crew memoirs, and newspaper accounts, to tell the story of the raider’s 58,000-mile journey. Though the book occasionally bogs down in the details of petty squabbles among the crew, it is a brisk and engaging read.

The Shenandoah was purchased by a Southern agent in Liverpool in the fall of 1864. Originally named the Sea King, she was a 220-foot auxiliary steamer, a ship powered by both sails and steam. To get around British neutrality, she embarked from Liverpool under a cover story that she was traveling to Bombay to buy coal. The crew then transformed her from merchant vessel to raider on the rolling ocean, with a skeleton crew.

Waddell had only the vaguest orders, to harass Northern trade and ditch the ship if trouble arose. At first, the Shenandoah needed to capture other ships just to survive—to gather necessary supplies and a full crew. After the captures were stripped of their valuables and their passengers were transferred, they would be set on fire or sunk. Twenty-four-year-old First Lieutenant William Whittle described watching one such ship succumb to flames: “The sight was grand and awful.” But he and the rest of the crew quickly developed a taste for the job and sometimes captured five ships in a day. A couple of months after his initial queasiness, Whittle noted in his journal, “I have rarely seen any thing which is more beautifully grand than a ship burning at sea.”

Men from the captured ships were either left at the next port or persuaded to join the crew, succumbing sometimes to Waddell’s stirring oratory and sometimes to nights in leg irons or “triced” up by their thumbs. Waddell was particularly cruel to black sailors. Because of his very rough recruitment methods, the crew was motley and occasionally unruly.

On January 25, 1865, with the Southern army in a shambles and Sherman marching to the sea, the Shenandoah docked in Melbourne. The ship was swamped by curiosity-seekers, and the U.S. Consul was sent into hysterics. It did take some diplomatic wangling to get her back out to sea, but after 23 days in Melbourne she set sail, with 42 stowaways, eager for adventure and notoriety.

While the men were enjoying shore leave at Ascension Island a few months later, Richmond fell and Robert E. Lee surrendered. But the crew sailed on in blissful ignorance, occasionally getting months-old news of the faltering Rebel cause but resolutely refusing to believe it. Chaffin writes, “From the moment that [Waddell] first set foot on the steamer’s quarterdeck, he knew that . . . he sailed in legally murky waters. But what he didn’t know, couldn’t know, was that because of that document signed at Appomattox Courthouse, those waters had suddenly become infinitely murkier, much more a sea of gray than he could have imagined.”

Braving fearful gales and inching through grinding ice floes in subfreezing temperatures, the crew battled their way to the Artic. Toward the end of June they captured the Milo, a New England whaler. The captain insisted that the war was over, but Waddell ignored him. On June 28 they found nine ships clustered around a whaleboat with a punctured hull. They captured all ten, rounding up the mystified crews, who thought the hostilities had ended. One lieutenant noted with relish, “This day we gave the hardest blow that Yankee commerce has yet received.”

Then on August 2 the Shenandoah tried to take another ship, but its captain handed over a newspaper announcing the South’s demise. Now the men had to contend with not only the sting of defeat but also the fact that for the past four months they had been common pirates. With their hull full of plundered goods, they had to race to a safe port were they could surrender. It was “running a very gauntlet of life to hope to escape all these dangers unscathed,” one officer wrote in his journal.

With a dwindling food supply and a captain wracked with indecision worthy of Hamlet, the men eventually made it to safety, but their illegal raids were not totally unappreciated. Jefferson Davis wrote in his memoir about his one glimmer of pride during his confinement in a Northern prison: “The Confederate flag no longer floated on land, but one gallant sailor still unfurled it on the Pacific.”

—Elizabeth D. Hoover is a former editor at American Heritage magazine.