Spying in America: Espionage from the Revolutionary War to the Dawn of the Cold War

6. Allan Pinkerton and Union Counterintelligence

  71 6 Allan Pinkerton and Union Counterintelligence What a strange time it was! Who knew his neighbor? Who was a traitor and who a patriot? The hero of to-day was the suspected of tomorrow. . . . There were traitors in the most secret council-chambers. Generals, senators, and secretaries looked at each other with suspicious eyes. . . . It is a great wonder that the city of Washington was not betrayed, burned, and destroyed a half-dozen times. Mary Elizabeth Wilson Sherwood, Epistle to Posterity, “On Spying.” Allan Pinkerton was born in Scotland into the family of a Glasgow corrections officer. After he and his wife emigrated to America, he entered the Chicago Police Department and became its first detective at thirty years of age. He then established his own private detective agency, which was hired by railroad companies to thwart increasing incidents of train robberies . While on assignment for a railroad in 1861, he was tipped off to a secessionist plot to assassinate newly elected President Lincoln while he traveled by train to his inauguration in Washington. Pinkerton’s detectives infiltrated the cabal and safely arranged Lincoln’s clandestine travel to the inauguration. 72 The Civil War PinkertonhadworkedfortheIllinoisCentralRailroad and had befriended its president, George McClellan, a former military officer. After war broke out, McClellan returned to service to command the Army of the Ohio and hired Pinkerton to gather intelligence for him. After the Union’s crushing defeat at Bull Run in July 1861, Lincoln appointed McClellan commander in chief of the Union Army, and Pinkerton joined him in Washington as his intelligence chief. Pinkerton was given dual responsibility by McClellan for combating espionage in pro-rebel Washington and obtaining intelligence on the Confederate army. Although Pinkerton only worked for the army and had no government-wide authority, he simply assumed responsibility for both missions throughout the Union. In his memoirs, which he wrote after the war, he dubbed himself “the chief of the United States Secret Service.” His office was buried in the army provost marshal’s office and its reports were submitted under the letterhead of the Headquarters City Guard, an innocuous cover title to mask its clandestine activities. A year later, Secretary of War Edwin Stanton would launch a rival service under Lafayette Baker to combat espionage in Washington. Pinkerton and Baker shared one common trait, their mutual proclivity toward romantic fiction. Both spy hunters wrote memoirs after the war to justify their wartime intelligence activities, but the accounts were seriously marred by lack of facts and self-promoting yarns of derring-do. Pinkerton’s memory of events could not be challenged by any records because all his files were destroyed in the Chicago fire of 1871. Pinkerton undoubtedly felt the need to defend his record because he was severely criticized for his failure in intelligence collection. His staff of about eighteen men and women was made up of police officers like Pinkerton who were steeped in criminal investigations but inexperienced in intelligence gathering.1 Most just fanned out behind enemy lines to scout Confederate troops and elicit information from unsuspecting rebels . By the end of 1861, the first year of the war, only five of Pinkerton’s men were actually in enemy territory; the rest of his intelligence collectors were focusing on interrogations of prisoners, whose information was woefully outdated.2 Pinkerton’s unit failed to recruit a single spy in the Confederate government with direct access to information on Southern plans and intentions. 73 Allan Pinkerton and Union Counterintelligence Pinkerton’s primary flaw as an intelligence collector was pandering to McClellan by shaping the low-level intelligence he received to conform to the general’s preconceived views. McClellan was a notoriously cautious commander, prone to act only when he believed he had overwhelming forces to engage the enemy. At one point, an exasperated President Lincoln sarcastically noted, “If McClellan is not using the army, I would like to borrow it.”3 McClellan’s decisions to avoid combat were reinforced by Pinkerton’s grossly inflated reports of enemy troop strengths. In one instance Pinkerton “analyzed” his agent’s reports to advise McClellan that Robert E. Lee had almost 100,000 troops in his Army of Northern Virginia, more than double the actual number.4 In another case McClellan received an unexpected treasure trove of intelligence not from Pinkerton’s agents but from a mistakenly discarded Confederate document. In September 1862 Union soldiers discovered three cigars in...