The Confederate Secret Service: A little-known Civil War story
by Art Gould
Special to The Star
Jul 17, 2011 | 6388 views |  0 comments | 5 5 recommendations | email to a friend | print
It was Nov. 24, 1864 – just one day after the nation’s second annual official Thanksgiving Day. Operating from a base in Toronto, Canada, agents of the Confederate States of America’s Secret Service launched an attack on New York City. A month earlier, the Confederate spies had attacked the small town of St. Albans, Vt., as a warm-up for their grander plan of torching Manhattan.

It’s a little-known story that might well be overshadowed in the many events commemorating the 150th anniversary of the Civil War.

Although the Confederate spies failed to ignite any buildings at St. Albans, near Lake Champlain, they did rob three local banks of $210,000. Undeterred by their ineptitude as incendiaries and their lack of professional spy craft, but flush with the Vermont banks’ cash, the CSA Secret Service forged ahead with its wildly ambitious plan to set at least 20 fires in New York City, from Wall Street all the way north to 26th Street, including five hotel fires at the future site of the World Trade Center, “Ground Zero.”

A strategic goal of the agents’ mission was to ignite an armed rebellion against the Union by anti-war, anti-government Northerners known as Copperheads. But in the end, the Confederate fires failed to incinerate New York City, and a war against the Union by a Northwestern Confederacy of Copperheads never materialized.

Historian Clint Johnson raises the essential questions about the CSA Secret Service’s conspiracy in his extraordinary new book, “A Vast and Fiendish Plot:” The Confederate Attack on New York City (Citadel Press, $15.95). How was it possible for eight battle-hardened Confederate soldiers, including Alabama native Capt. Robert Cobb Kennedy, who had no spying or special sabotage experience, to mount such an attack? How did they manage, if only partially, to set fire to the largest city in America (population 800,000, circa 1864), the financial capital of the Union, a city with a vast harbor system responsible for most of the nation’s trade and protected by the threat of Union troops stationed nearby?

But what really surprises Johnson, the author of 11 books on the Civil War, is that the attack on New York City happened in the first place. The city was pro-South before and even during the Civil War.

The assault, Johnson writes, “is the story of how two best friends, the slave-holding South and slave-trading New York City, fell out of love with each other … and why the Confederacy targeted Manhattan because of the devastation the South had suffered at the hands of the Union between 1861 and 1864.”

Although Johnson relates the adventure of the Confederate conspiracy in a gripping manner, his most important historical insights are reserved for the symbiotic relationship between New York City and the South prior to 1861.

New York “became an economic powerhouse in the first half of the 19th century because Southern cotton literally and figuratively flowed through its port. … What was good for the South was good for New York. … New York City and the South had made each other prosperous.”

Any surprise at the Confederate attack on Manhattan reflects the longstanding sweetheart relationship between the city’s investment bankers, merchants, shippers and insurance brokers and the Southern cotton plantations. The planters needed the city to fund, insure, supply, sell and ship their cotton harvests. New York investment money was also funding the means to grow and reap the cotton: slave labor.

Despite the fact that slavery was outlawed in the state of New York in 1799 and the slave trade was abolished nationally in 1808, New York City investors continued to outfit ships that sailed from American ports to West Africa, where they freighted men, women and children destined for Caribbean slave markets.

“Between January 1859 and August 1860, at least 85 slaving voyages originated from New York’s harbor, transporting between 30,000 and 60,000 slaves from Africa to Cuba.” Johnson reports. Without New York money, there was no U.S. slave trade.

Most important: All the money flowed in a circle starting and ending in Manhattan, with stops along the way in Europe, Africa, Cuba and the southern United States. But it was the New York bankers and merchants who grew fabulously wealthy, keeping 40 cents of every dollar along the way. For the city’s investors, this was a neat, simple and profitable arrangement. It was why New York supported the South even during the war.

But by 1864, after three dreadful years of fighting, the Confederates were ready to take down what had once been the financial epicenter of their world in an act of revenge.

Why? Johnson has identified three primary motives:

• The Northern election of 1864.

• Revenge for the Union Army’s mass destruction of life and property by Gen. Grant at Vicksburg, Gen. Sheridan in Virginia’s Shenandoah Valley, and Gen. Sherman in Georgia.

• The farfetched belief that burning New York City would cause a rebellion in Illinois and Indiana against the Union.

By 1864, Confederate leaders believed that Lincoln was vulnerable in his bid for re-election, and they were right. In 1860, Lincoln had barely won office with only 39.8 percent of the popular vote in a four-way presidential contest. “Until Lincoln was actually nominated, the idea that an unpopular, one-term Congressman from Illinois might be elected President of the United States had not crossed the minds of New York City’s merchants, bankers, industrialists and millionaires,” Johnson writes.

Lincoln was not a president much revered in his own time. By the fall of 1864, he was wildly unpopular. After three years of bloody conflict, during which Lincoln had suspended the writ of habeas corpus, raised troops by executive decree and signed the Emancipation Proclamation, he was reviled in the North as well as the South.

The Confederates were counting on strong anti-Lincoln sentiment in the North to sweep a Democrat into office, one who would make peace with the South. Burning down New York City might be a way to make that happen.

However, riding on the coattails of the Union generals’ popular successes in the summer of 1864, Lincoln was re-elected in a landslide. Regardless of Lincoln’s victory and the failure of an army of Copperheads to materialize, the CSA Secret Service was determined to move ahead with its plans for revenge.

The incendiary weapon of choice the Confederate agents used against New York City was a chemical compound called Greek Fire. The liquid was a mixture of sulfur, pitch, dissolved niter, naphtha and petroleum. Greek Fire was able to spontaneously combust if the mixture was put together properly and exposed to a strong supply of oxygen.

While the Confederates’ efforts at sabotage were often sad imitations of sound spy craft, two of their errors were particularly negligent. The agents failed to select the most advantageous sites for setting fires, and, for some inexplicable reason, the demolition team showed no interest in learning how to properly handle Greek Fire.

The agents selected 21 hotels in New York City, hoping to set them ablaze and burn down all of Manhattan. They ignored or overlooked really dangerous targets like the harbor’s flammable wooden docks, the city’s gas works and a huge naphtha factory adjacent to vast lumberyards.

The eight Confederates had so little experience with Greek Fire that they set room fires at the hotels without opening any windows to provide a reliable source of oxygen. Without a steady stream of fresh air, most of the fires simply smoldered and extinguished themselves, or were quickly discovered and doused by hotel staff.

“Eight Confederates who were brave enough to walk into a city of 814,000 people were too excited about finally having the chance to act than they were about testing themselves and their weapons to see if both were actually ready to attack New York City,” Johnson writes.

Only three of the eight Confederate conspirators were ever captured after the failed sabotage. Only one was tried and found guilty of spying and arson at a secret military trial in New York. That Confederate officer was Alabama native Capt. Robert Cobb Kennedy.

He was hanged at Fort Lafayette, N.Y., on March 25, 1865.

Art Gould is a former newspaper reporter and book publisher. He lives in Anniston.
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