Originally broadcast on August 18, 1995 - In part 51 of our Civil War series, Virginia Tech history professor James Robertson discusses espionage during the Civil War and profiles some of its most colorful characters, including Alan Pinkerton, Crazy Bet and Belle Boyd, the siren of the Shenandoah.
#51 – Espionage
Every now and then, the subject of spies comes up in Civil War history. What we know of espionage activities in the 1860s is both flimsy and exaggerated. It is also a mixture of comedy and courage.
For both sides, spying in the Civil War was an amateurish enterprise. America in the mid-19th Century had no enemies in the New World. Hence, covert operations and so-called “spy schools” did not exist. Not one group of professional agents stood prepared to go into enemy country. Civil War espionage consisted of ordinary citizens and soldiers who loved their cause enough to risk their lives on its behalf. Neither side maintained sufficient records to enable us today to know exactly what each accomplished.
The best-known of the Northern agents was Allan Pinkerton, a Scotch immigrant who at the age of thirty had become Chicago’s first police detective. In February, 1861, Pinkerton foiled a plot in Maryland to assassinate Abraham Lincoln as the President-elect made his way to Washington. Pinkerton also obtained useful information for young General George McClellan, campaigning in the mountains of western Virginia. As a result, Pinkerton became head of the newly established U. S. Secret Service.
He and his men were not so much secret agents as they were private detectives working for the Union government. Pinkerton had a two-fold mission: to ferret out Southern sympathizers in Washington, and to collect military data about the enemy in the field. Pinkerton succeeded well in the first endeavor; he failed miserably as a military spy. He was forever overestimating the size of enemy numbers. In April, 1862, he and McClellan together put Confederate strength on the Virginia peninsula at 120,000 soldiers. At the time, the actual figure was closer to 17,000 men.
The first Confederate spy to gain widespread attention was Mrs. Rose O’Neal Greenhow. Attractive, in her mid-forties when the Civil War began, she was the widow of a former State Department official. Mrs. Greenhow was also a popular Washington hostess who had known every president from Andrew Jackson through James Buchanan. In 1861, wine flowed freely at her gala banquets; tongues wagged loosely; and Mrs. Greenhow sent cipher messages on a regular basis to Confederate officials.
Jailed for a time, she then went to England to solicit funds for the Confederacy. Mrs. Greenhow was returning to the South in October, 1864, when her ship sank in a storm near Wilmington, North Carolina.
Belle Boyd, the so-called “Siren of the Shenandoah”, was a daring young agent in the Valley of Virginia. She possessed more desire than knowledge about espionage. Her exploits are difficult to pinpoint because she habitually embellished them in the years after the war. Both Miss Boyd and Mrs. Greenhow had flamboyant personalities and outspoken devotion to the Southern cause. These things blocked the low profile that would have made them more successful as spies.
Elizabeth Van Lew, a doughty Richmond spinster, was a successful Union agent because she dressed and behaved in such an odd fashion that no one took her seriously. Richmonders called her “Crazy Bet”. Yet General U. S. Grant later stated that Miss Van Lew gave him “the most valuable information received from Richmond during the war”.
Espionage in the Civil War was only partially successful. The lack of trained agents was not the problem as much as it was how to process and utilize the information obtained. Every army had a spy or two, and they kept headquarters informed of anything they uncovered. Analyzing the information to maximum advantage did not occur often.
Individual spy stories are full of inventiveness, suspense, and courage. Each agent did the best he or she could. In the end, however, one suspects that for every James Bond there might have been, also in evidence were at least two Maxwell Smarts.