Security Leaks that made History

Security leaks can make history. Notably, mistakes led to security leaks that changed the course of World War I and the American Civil War.

Sometimes, history-changing security leaks are deliberate. Conversely, most history-altering security leaks are accidents or mistakes.

Predictably, the greatest history-changing security leaks occur during wartime. Ironically, the public and most of the soldiers and sailors fighting in the wars are never aware of those leaks until long after the conflicts end.

Some History Changing Leaks Include:

The Magdeburg Codebook

The greatest security leak of World War I occurred on 26 August 1914, less than a month after the Great War’s start.

The German cruiser SMS Magdeburg was part of a small force of ships ordered to attack Russian shipping and shore installations in the Gulf of Finland. The Magdeburg’s navigator became lost in fog at the Gulf’s entrance and got the ship stuck on a shoal.

The 4,570 ton cruiser could not move and an effort to pull her out with a torpedo boat failed. The captain Richard Habenicht decided to abandon and destroy the Magdeburg because she was in Russian waters.

Moreover, the stuck ship was visible from a Russian lighthouse. Somebody on shore alerted the Russian Navy, which dispatched cruisers and torpedo boats to investigate.

During the Magdeburg’s evacuation, Habenicht made a mistake that altered the course of World War I. Habenicht failed to destroy two of the ship’s codebooks.

The codebooks were critical intelligence because they contained the ciphers that kept all the Imperial German Navy’s radio communications secret. Anybody who got the codebooks could decrypt and read the orders German Admirals sent to their ships at sea.

The Magdeburg’s crew destroyed one codebook and threw another overboard. Unfortunately, Habenicht forgot that there was a third codebook onboard in a locker in his cabin.

As Russian cruisers approached, the Magdeburg’s crewtried to blow her up. However, the explosion only partially destroyed the ship. Much of the Magdeburg’s superstructure; including Habenicht’s cabin, was still intact.

As most of the Magdeburg’s crew fled on the German torpedo boat V-26, a Russian boarding party approached the cruiser. The boarding party’s commander, Lieutenant Galibin, found the codebook in Habenicht’s locker.

Furthermore, Russian divers found the codebook that the Magdeburg’s crew had thrown overboard. Hence, the Imperial Russian Navy had the Imperial German Navy’s most-guarded secret; the Singalbuch (codebook) used by radio operators.

Ironically, the codes did the Russians little good because their navy was in sorry shape. However, the codes were invaluable to Russia’s ally, the British Empire.

To get more British help and money, three Russian naval officers took the Signalbuch to the Admiralty, the headquarters of the Royal Navy, in London. There the First Lord of the Admiralty himself, Winston S. Churchill, took possession of the German codebook.

The Signalbuch became the basis of Britain’s legendary World War I code-breaking effort. British code breakers in the Admiralty’s Room 40 read most of the German Admirals’ radio commands to their ships at sea.

Consequently, the British Admirals could counter most of the Germans’ moves. Kaiser Wilhelm II’s magnificent surface fleet was useless because the Royal Navy could block its moves. Every time the Kaiser’s fleet left port, British ships were there to fight it.

The German surface fleet could not attack Britain, or to send naval forces to help their ally, the Turks, in Mediterranean. With their surface fleet useless, the desperate Germans turned to U-Boats or submarines.

The German strategy was to starve the British into submission by having U-Boats sink the freighters hauling food and supplies to the United Kingdom and the armies fighting in France. The strategy backfired, because it gave American President Woodrow Wilson (D-New Jersey) a pretext for entering World War I on the British side.

Conversely, German arrogance led to the catastrophe. German naval commanders refused to believe that their enemies could crack the German codes and refused to change them until late in the war, author David Kahn writes.

The presence of American troops in France gave the British and French generals the forces they needed to beat back the final German offensive and win the war. Ironically, by that time, the Russians had lost and their empire had collapsed in revolution. Notably, Lieutenant Galibin; the man who had captured the code books, was in a German prisoner of war camp.

Germany surrendered in 1918. The victorious powers interned the Kaiser’s powerful fleet at the British Naval base in Scapa Flow, Scotland. German sailors later scuttled most of their warships to keep them out of British hands.

One consequence of the Magdeburg codes was that His Majesty’s Government established the world’s first signals intelligence agency; the Government Code & Cypher School (GC&SS), in 1919. The GC&SS still exists as the Government Communications Headquarters (GCHQ). They modeled the American National Security Agency (NSA) on the GCHQ.

The Magdeburg code books had a powerful effect upon World War II. The success of Room 40 inspired even greater British and American code breaking efforts in the Second World War. Notably, British sailors in World War II were on the lookout for German codes and encryption devices, which they passed onto the GC&SS.

Thus two German mistakes in a minor naval battle altered the course of history. By getting their ship stuck and forgetting to destroy a codebook, the Magdeburg’s crew made history.

For a detailed account of the Magdeburg codebooks and their effect on history see Seizing the Enigma: The Race to Break the German U-Boats Codes, 1939-1943 by David Kahn.

The Affair of the Confederate Cigars

Another history-changing security breach involved three cigars. Those cigars probably changed the course of the American Civil War and freed millions of African-Americans from slavery.

On 13 September 1863, two Union soldiers; Sergeant John Bloss and Corporal Barton W. Mitchell were taking a break from a march near Frederick, Maryland. In a field, Bloss and Mitchell found three cigars wrapped in a piece of paper.

Incredibly, the cigar wrapper was Special Order No. 191, Headquarters, Army of Northern Virginia. Special Order No. 191 was Confederate commander Robert E. Lee’s plan for an invasion of Maryland and Pennsylvania. Special Order No. 191 detailed the route the Army of Northern Virginia would take.

Bloss and Mitchell passed Special Order No. 191 up the chain of command. Somewhere along the chain, a Union General Samuel Pittman saw the handwritten order. On the paper, Pittman recognized the handwriting of an old army buddy, Robert Chilton, who was serving as Lee’s adjutant general (chief of staff).

As a result, Pittman took the order to General George B. McClellan, the commander of the Union Army of the Potomac. Once he saw the order, McClellan knew where Lee was going.

Unfortunately, the Army of the Potomac was slow to move and unable to attack the Army of Northern Virginia on the march where it was most vulnerable. However, the Army of the Potomac could stop Lee’s invasion.

Defeat at Antietam forced Lee to abandon his offensive and retreat to Virginia. The North was safe from invasion and Lee’s efforts to cut Washington DC off from the rest of the Union failed.

The victory at Antietam gave Union President Abraham Lincoln (R-Illinois) political cover to issue the Emancipation Proclamation. The Emancipation Proclamation freed slaves in the Confederate States.

Since the vast majority of slaves were in the Confederacy, the Proclamation freed most of America’s slaves. However, the Emancipation Proclamation did not abolish slavery. Hence, slaves in states loyal to the Union had to wait until the 13th Amendment in 1865 for their freedom.

The Proclamation transformed the Civil War from a conflict over states’ rights to a crusade against slavery. One result of the Proclamation was to make a British intervention on the Confederate side impossible.

To explain, most British people were against slavery. As long as both sides in the Civil War embraced slavery, British support for the Confederacy was a political possibility.

British intervention could have led to Confederate victory because the Royal Navy was powerful enough to break the Union blockade of Southern ports. A broken blockade could have allowed the Confederates to import the weapons and munitions they needed the win the war.

Thus, two Union soldiers changed American history and freed millions of enslaved people by picking up a bundle of cigars. There is an intriguing mystery about the cigars.

Nobody knows who left the cigars and Special Order No. 191 for Bloss and Mitchell to find. Was the order left by a Union spy, a Confederate traitor, a British agent, or a slave who knew how to read? Some Confederate officers brought slave servants to war with them. Did somebody deliberately wrap Special Order No. 191 around the cigars, hoping a Union soldier would pick them up?

Moreover, were Bloss and Mitchell just resting, or were they were under orders to “find” the cigars? Notably, the cigar find sounds like a dead drop. A dead drop is a classic piece of espionage tradecraft in which a spy leaves hidden intelligence for another agent to pickup.

So yes, information leaks can change history. Hence, history justifies the paranoia leaders such as US Presidents Donald J. Trump (R-Florida) and Joe Biden (D-Delaware) have about leaks.