By: Sebastian Kim

President Lincoln with Spymaster Allan Pinkerton (to his right)
President Lincoln with Spymaster Allan Pinkerton (to his right)
President Lincoln with Spymaster Allan Pinkerton (to his right)


During the Civil War, spies and spy activity was everywhere. However, it is not the James Bond-esque spying that we know and love today. Spying during the time of the Civil war was more of a, "political chess game" than anything else. Each side was fully aware of the presence of spies, but lack of technology and a few other variables rendered them virtually defenseless against even the most basic of spying techniques. Both sides effectively used spy tactics to aid there cause and revolutionized the world of espionage. The international spying community today owes a great bit of gratitude to the spies of so many years ago.

Confederate Spies

At the start of the Civil War (in 1861) neither the north or south had any intelligence bureau. However, the south was the first to achieve this. The south, however, was running a spy ring out of Washington D.C. that was established sometime between 1860 and 1861 by Thomas Jordan. At this time in history, the D.C. area was teaming with confederate spies plotting against the union (see video). Thomas Jordan was a former US army officer who became a Confederate Colonel. Jordan recognized early during the war thatinserting intelligence agents into northern military and political hubs would be of great value. During the Summer of 1861, Jordan turned over the command of this spy ring to Rose
O'Neal Greenhow.

Rose Greenhow
Rose Greenhow

Rose Greenhow

Greenhow's stationing in D.C. allowed her to quite easily obtain and wire intelligence back to the south. The vast of majority of this information reportedly was obtained through an, "infatuated suitor," Henry Wilson of Massachusetts, the chairman of the senate Military Affairs Committee. Greenhow's intelligence was smuggled to the Confederacy through an intricate series of couriers. Two other confederate intelligenceagencies in the D.C. area were under the command of cavalry men turned spies: Captain Thomas N. Conrad and Private J. Franklin Stringfellow. These highly lucrative operations were connected to the Confederacy's first major Secret Service Bureau formed in 1862.

The leader of this bureau was Major William Norris who in time would oversee the development of dozens of intelligence and counterintelligence agents who worked along the "secret line (and "underground" path between Richmond and the DC area)." Norris and his partner Captain Charles Cawood extended operations as far north as Canada, making it possibly the most successful ring of intelligence the war ever saw. A second agency was established under the command of Brigadier General Gabriel J. Rains, however it was poorly managed and, as a result, was not nearly as successful as Norris' agency.

In addition to these government sanctioned intelligence operations, the Confederacy was also aided (and aided very successfully) by an abundance of civilian intelligence operations. The most acclaimed and heralded of these was Belle Boyd, who risked her life to bring information to "Stonewall" Jackson during his Shendoah Valley Campaign of 1862. Less heralded was James Harrison, a traveling Richmond actor who late in 1863 rode to General Robert E. Lee's Pennsylvania headquarters with word that the Army of the Potomac was about to enter the Keystone State in pursuit. The news urged Lee bring together his massive army prior to Gettysburg.
Although the Confederacy experienced great success with individual civilian spies, their larger scale intelligence agencies were largely unsuccessful.

Union Spies

The Union waited for the war to go hot to establish any form of government sanctioned espionage. In mid-1861, Allan Pinkerton established the first bureau of intelligence in the Union. He was also the founder of the famous Chicago Detective Agency. Pinkerton served in Mclellan's army and while doing so, he infiltrated the confederacy all the way to Stonewall Jackson before returning north with information regarding southern war plans. While he was travelling back north (to D.C. where Mclellan was) he practically singe handedly broke up Greenhow's confederate spy ring. Although Pinkerton's career in espionage was primarily successful, in 1862 he gave Mclellan wild estimates of the enemy's strength and numbers which hindered Mclellan's army significantly.

Allan Pinkerton
Allan Pinkerton
Allan Pinkerton

One spy that servedunder Pinkerton was a fellow names Timothy Webster. Webster is known today as the single most famous spy that Pinkerton ever had. He served as a double agent and made frequent trips across enemy lines. He travelled to places such as Baltimore, Lousville, Memphis and even infiltrated the militant Baltimore society of Confederate sympathizers known as the, "Knights of Liberty." Webster ended his career in 1862 but a series of events led to his arrest and execution that same year.

The North, like the south, was aided by a number of civilian spies both men and women. Female spies, in the event of their arrest, were usually spared the more harsh sentences for their actions. It was easy for anyone who wished to, to travel across state borders into enemy territory because of the two nations close proximity and origin. Some civilian spy operations were very elaborate and in some cases, successful. Probably the most noted and most publicized of these civilian spy operations was when John J. Andrews attempted sabotage Confederate Rail Lines. Although Andrews' plan failed, it still received a not so insignificant amount of media coverage. It was extremely easy for any Union man or woman cross into an enemy state/town and blend in almost perfectly. However, there were many more Union spies in uniform than there were confederate spies in uniform.

In general, Union espionage proved more successful collectively than the Confederacy ever was. A good example of the Unions superb abilities in espionage is when Major Henry Young of Rhode Island and his band of just under sixty men intercepted confederate telegraph messages and rerouted supply trains that Lee's army was in dire need of.
Collectively, Union espionage proved itself to be far more efficient and beneficial than confederate espionage.

Elizabeth Van Lew

Possibly the most famous of all the spies, both male and female, was Elizabeth Van Lew. Elizabeth was a well educated, "southern belle" of Richmond. Her parents were Northerners, but had moved to Richmond when they married. Elizabeth was sent to Philadelphia as a young woman for school and became highly influenced by the strong abolitionist sentiments that were present in the city. Elizabeth remained un-married for her entire life (commonly attributed to a serious relationship mishap early in her life). Her family was well respected in Richmond, lived in a three and a half story mansion, and frequently hosted elaborate balls and garden parties. Elizabeth's career in espionage began when she learned of the horrible living conditions Union soldiers were forced to endure after being captured.

Before long, Elizabeth was sheltering escaped Union soldiers and helping guide them towards freedom. She was very cautious not to let on that she was a Union sympathizer, let alone the fact that she was harboring enemies of the state. Union supporters in the Confederacy could have their property taken away and be imprisoned as punishment.
Through various connection with Union and Confederate soldiers alike, Elizabeth learned of Confederate numbers and positions throughout the army. She, through her younger brother who had fled Richmond and gone North after the Confederacy had attempted to draft him,developed a connection with Union General Ulysses Grant. Elizabeth, and her long list of Union supporters and troops, was able to put together a sort of Spy Network.

Included in this network were the Van Lew's own servants who made trips the family farm (about a quarter mile away from their mansion) carrying baskets that rarely attracted any attention, but were in-fact carrying detailed pieces of information about the Confederacy. The baskets would be passed on to Union, "scouts," or spies in uniform, to be delivered to people such as General Grant. In some cases, the baskets were sometimes filled with hollowed out eggs filled with information. In other cases, servants hid secret messages in the soles of their shoes. Before long, Elizabeth's spy network had become a quick and lucrative operation, sending information to Union commanders up to three times a week. She ended up using up, almost entirely, her entire family fortune in efforts to support the Union cause. Running her spy network proved to be extremely costly (and dangerous. Who knows how the war would have been without Elizabeth Van Lew: A truly important woman to the Union

Elizabeth Van Lew
Elizabeth Van Lew

Elizabeth Van Lew

Intelligence Courier Systems

For Civil War spies, getting the information was relatively easy in comparison to the difficult task of getting the intelligence back to either side in time for it to be of use. Sadly, some spies had no appreciation for the time sensitivity of their information, but those who did developed unique ways of transporting their information to the people it concerned. In some cases, spies even sprinted through enemy lines to present pieces of intelligence in person. Staying in one place and finding other ways than delivering information personally was the safest way to conduct operations because making frequent trips back and forth from one side to another only increased a spy's chances of being discovered and executed.
Later on in the war, courier systems came into play making it easier for spy's to get there information back to their side. It was around this times that an explosion of Union courier systems came about: Organizations such as the Legal League were used particularly by negro spies like John Scobell. Union sympathizer organizations such as the Order of the Heroes, the Peace Society, and the Peace and Constitution Society had couriers that were used in emergency situations. When the Union organized its own intelligence organizations, they instated specific officers with the one and only task of transporting information thereby making other courier organizations seem less reliable and in general obsolete.
Not so surprisingly, the Union had a much more efficient courier system than the Union in part because it had had an intelligence network in D.C. months before the war even began. The earliest courier path was known as, "the Doctors line," because it consisted of both real and fake doctors that were operating in the D.C. area. Doctors were suitable couriers because they were often called out at night and carries black leather bags that were perfect for carrying secret information places. The most famous couriers of the Confederacy, however, were the couriers that were used by Rose O'Neal Greenhow who were never caught
and were highly effective.
An example of what a fake doctor's bag may have looked like

Intelligence Gathering by Cryptology

Cryptology (coded forms of writing) had been alive in the States since the Revolutionary War, but cryptology was forever changed by a single invention. This invention was, the telegraph. The telegraph allowed the military to communicate quickly with each other without having to fret about couriers being captured by an enemy or having to deliver information by hand. However, early on it was discovered that telegraph lines could be tapped and the enemy could receive a feast of information that was never intended for their eyes. This interception of messages ended up playing a highly significant role in the initiation of battles. In order to avoid this, an encoded system called,"Route Ciphers," (created by Anson Stager) was devised for use by the Union (see example). Not a single one of these encoded messages was ever deciphered by the Confederacy during the war. Towards the end, the Confederacy was beginning to become desperate and even went so far as to publish intercepted messages in the paper asking for public aid, but to no avail.

An example of "Route Ciphers"
An example of "Route Ciphers"


"Espionage In The Civil War." The American Civil War Home Page. Web. 19 May 2011. <>.

Markle, Donald E. Spies and Spymasters of the Civil War. New York: Hippocrene, 1994. Print.

Winkler, H. Donald. Stealing Secrets: How a Few Daring Women Deceived Generals, Impacted Battles, and Altered the Course of the Civil War. Naperville, IL: Cumberland House, 2010. Print. (primary source)

Wagner, Heather Lehr. Spies in the Civil War. New York: Chelsea House, 2009. Print.

external image empty.png Notes for Spies.doc