Allan Pinkerton was not the first American detective, but was perhaps, the most famous. Scottish-born Pinkerton worked as detective for the Chicago police department before starting the Pinkerton detective agency in the 1850s. The Pinkerton Agency’s unblinking eye logo and motto “We never sleep” gave birth to the instantly recognisable nickname “private eye” for detectives. Pinkerton was the model for the hardboiled detective fiction of Dashiell Hammett and Raymond Chandler. Pinkerton’s biggest moment came just before the civil war when he exposed a plot in Baltimore to kill president-elect Abraham Lincoln, as Daniel Stashower’s The Hour of Peril explores.
Pinkerton was born in 1819 in the poverty-ridden Gorbals area of Glasgow. His weaver father died young and Allan learned the craft of barrel-making from Glasgow cooper William McAuley. He travelled around as a tramp cooper, joined the cooper’s union and became Glasgow’s “most ardent Chartist”. In 1838 the Chartist movement presented its people’s charter demanding universal suffrage, equal pay and other democratic reforms. After Parliament imprisoned leaders and rejected a petition signed by a million people, the movement fractured with many demanding violent action.
Pinkerton attended a protest rally in Newport, Wales where Chartists ran into a military contingent who killed 22 and arrested many others. Pinkerton said he escaped, “more like thieves than honest men” though the experience helped him “reach a nobler and happier condition of life.” He became a Chartist leader and in 1842 authorities issued a warrant for his arrest. Friends hid him for months before he followed Chartist escapees to America.
Allan married his 15-year-old girlfriend Joan Carfrae and they moved to Chicago where he got a job making barrels at a brewery. Wanting to start his own business, they moved west to the auspiciously named Dundee, Illinois, founded by Scottish farmers. The hard-working Pinkerton set up shop as Dundee’s “ONLY AND ORIGINAL COOPER”. By 1846 he employed eight men. An avid reader, he was enthralled by escaped slave Frederick Douglass’s autobiography and he became an ardent abolitionist. The American Anti-Slavery Society put him to work on the Underground Railroad, a secret network of meeting points, back channel routes and safe houses which ferried runaway slaves to the north. The name came from a disgruntled slaveholder whose slaves had disappeared, reportedly saying, “the damned abolitionists must have a railroad under the ground.” Though harbouring fugitive slaves was illegal, Pinkerton’s log cabin became an important stop on the line north to Wisconsin and Canada.
One day Pinkerton became curious about an island on a local river which he believed was used by criminals. After sneaking onto the island and watching men at a campfire, he told the sheriff. A posse discovered a counterfeiting ring and Pinkerton was the hero of the hour. When another suspicious stranger arrived in Dundee, shopkeepers asked Pinkerton to investigate. Pinkerton was hesitant but when they said he could catch the intruders red-handed, he was convinced, believing he could become “a great detective”. He posed as a “country gawker” and gradually got into the stranger’s confidence. The man’s name was John Craig and he wanted a local accomplice in a lucrative scheme.
Pinkerton agreed to pass on Craig’s counterfeit bills and alerted the sheriff to the coming transaction, who provided genuine cash for the handover. But Pinkerton bungled the transfer and could not prove Craig accepted the money. Pinkerton doubled the bluff and asked Craig for more counterfeit money. They arranged to meet in a Chicago hotel and he tipped off constables. Pinkerton demanded Craig show him the money in advance, claiming he’d involved a lawyer. Craig feigned ignorance and Pinkerton signalled for a constable to make the arrest. Craig protested his innocence and had the support of onlookers. Pinkerton’s flimsy evidence was never tested in court as Craig mysteriously escaped prison. It seemed to confirm his guilt and Pinkerton was a hero again. Before long, he became Dundee’s deputy sheriff. His cooperage days were over. All the success that followed, he said, was “owed to John Craig.”
Pinkerton moved to Chicago to become deputy sheriff of Cook County in 1847. He moved quickly through the ranks, first to sheriff and then becoming Chicago’s first detective, known for his strength, daring and incorruptibility. In 1853 Pinkerton survived a shooting from behind, fortunate his arm took the blow. His survival added to his mythical reputation. He became a special agent for the Postal Service and went undercover to investigate money that routinely went missing in the mails. He befriended a corrupt employee and got him charged only to find out he was the city’s postmaster’s nephew. Desperate to find evidence and with his own career on the line, Pinkerton found a picture-frame at the man’s boarding house with thousands of dollars of incriminating bank drafts. The Chicago Press hailed Pinkerton as a detective without equal. Buoyed by praise, Pinkerton decided to go out on his own.
He later claimed he started the Pinkerton National Detective Agency in 1850 though the post office exploit did not happen until 1853. Either way, he was in the right job in the right place at the right time. As America expanded westward, Chicago boomed as a railway and shipping hub, spurring a new crime: train robbery. Pinkerton was ideally placed to track offenders across state boundaries as frontier justice was transforming into national authority. With no secret service until 1865, Pinkerton made up the rules as he went along. His principles were based on his Chartist roots and the example of great French detective Eugene-Francois Vidocq (the inspiration for Jean Valjean in Hugo’s Les Miserables). Pinkerton followed Vidocq enthusiastically in his use of disguises and cover identities. He worked with Illinois Central Railroad and while he did not meet company lawyer Abraham Lincoln, he became friends with senior executive George McClellan, a relationship that would tarnish his reputation after McClellan led the Union Army in the civil war.
The Pinkerton logo with its stern unblinking eye began to appear in correspondence, advertisements and legal documents. Pinkerton’s first employee was talented businessman George Bangs. Bangs ran the growing operation allowing Pinkerton to concentrate on managing his team of detectives. His most resourceful subordinates were 32-year-old Englishman Timothy Webster, a shrewd and courageous detective, and 22-year-old widow Kate Warne. Warne desperately wanted to be a detective and convinced a doubtful Pinkerton that a woman could “worm out secrets that are impossible for male detectives”. She quickly became an integral part of the operation, and managed her own team of female operatives. Warne proved her mettle in a 1858 case when she persuaded the wife of a corrupt employee of a mail express company to reveal where he had hidden packages of stolen money. The employee was still confident he could beat the charges in court only to realise with horror that a cellmate he had blabbed to was another Pinkerton employee. He pleaded guilty.
Despite the stiffer penalties of the 1850 Fugitive Slave Act, Pinkerton remained a supporter of the Underground Railroad. John Brown was a “bosom friend” and regular visitor to his house in Chicago. Pinkerton supported Brown’s incursions into “Bleeding Kansas” and in 1859 Brown tried to incite a slave rebellion with his notorious raid on Harpers Ferry federal armoury. Brown was overwhelmed by marines under Colonel Robert E. Lee and hanged, despite the efforts of Pinkerton and others to win a reprieve. Brown’s Raid heightened hatred between north and south. By the time Lincoln won the presidency 12 months later, secession fever was acute. In four months, seven deep south states left to form the Confederacy. Border slave states like Maryland remained in the Union, but were vulnerable. Pinkerton regularly visited the south and knew that many southerners wanted Lincoln killed. So did Lincoln. He received death threats in the mail and heard of plans to kill him as he journeyed from his Springfield, Illinois home to Washington for the inauguration.
Lincoln had other concerns including the Confederate threat to seize Fort Sumter in Charleston Harbour. Republican Senator William Seward, whom Lincoln had defeated for the presidential nomination and would become secretary of state, urged Lincoln to come to the capital early. This was difficult. Lincoln planned a grand tour of the northern cities that elected him, involving a long and difficult railroad journey across many different lines. The owner of the Baltimore and Ohio Railroad’s 500 miles of track was believed to be sympathetic to the rebels. Friends urged Lincoln to travel with a strong armed force, but he wanted to avoid the appearance of war.
In early 1861 the Philadelphia, Wilmington and Baltimore Railroad boss, Samuel Felton, heard rumours of a plot to disrupt the inauguration. Felton informed top army general Winfield Scott who was aware of the threat. However the ineffectual outgoing Buchanan presidential administration took no action. Though Congress held an inquiry, it too foresaw no interruption of government functions. Felton believed that only one man could prevent Lincoln’s likely assassination. On January 19 he made an urgent plea to “celebrated detective” Allan Pinkerton.
Pinkerton was quickly on the case. Felton told him it was part of a plot for Washington to fall into rebel hands. With six more states now joining the Confederacy, war was looming and Maryland’s legislature was debating whether to join it. Lincoln would have to pass through Baltimore on his way to Washington but was unlikely to receive a cordial welcome and there was no reception committee. Three lines converged on Baltimore and Pinkerton knew Felton’s railroad had to remain open to connect the capital to the north. With the inauguration just five weeks away, Pinkerton dispatched a large team to Baltimore, urging Felton to keep the operation secret.
Baltimore was then America’s fourth largest city. A centre of German and Irish immigration, its neighbourhoods were ruled by gangs like the Plug Uglies, Rip Raps and Blood Tubs who needed little provocation to turn violent. Pinkerton posed as a Southern stockbroker and distributed operatives including Warne and Webster across the city. They heard angry talk against the new president from pro-southern fire-eaters. Lincoln released his travel schedule to Washington, a complicated criss-crossing journey over 2000 miles on 18 railroads. Lincoln would travel in “open and public fashion” and arrive in Baltimore on February 23. He would only be in the city for two and a half hours to change trains to Washington at a different station, but that was time enough to carry out any plot. Lincoln’s small entourage included two army officers and self-appointed bodyguard, burly lawyer Ward Lamon.
In Baltimore, Cypriano Ferrandini’s barber shop was a centre of secessionist gossip. Ferrandini told Pinkerton that he wanted Lincoln dead to save the Union and he would be prepared to die to carry out the assassination. Pinkerton sent an urgent telegram to his old Chicago acquaintance and Illinois Senator Norman Judd, who was with the Lincoln delegation in Cincinnati. Judd believed the threat but wanted more information. These were jittery times. The electoral college was in session in Washington and though the New York Times worried about “the blowing up of the Capitol,” it concluded peacefully and ratified Lincoln’s win.
While Lincoln continued eastwards, Pinkerton met Baltimore’s police marshall George Kane. Appointed in 1860, Kane had stared down the mobs but advised against a procession in Lincoln’s honour. Though he guaranteed the president-elect’s safety through Baltimore, Pinkerton doubted his loyalty to the north. Then Pinkerton heard of a plot to blow up the railway bridge at Havre de Grace north of Baltimore. His operative Harry Davies was accepted into Ferrandini’s secret society, and heard Ferrandini say Lincoln would never become president. The society drew lots to see who would commit the murder. Pinkerton ordered Kate Warne to meet Lincoln’s party in New York and give Judd the latest information. Warne sent a cryptic telegram that read “today they offer ten for one.” This meant betting dens had ten to one odds against Lincoln surviving Baltimore.
In Washington, politicians gathered for a Peace Convention led by former president John Tyler. The convention failed but it heard more rumours of a Baltimore plot against Lincoln. Army chief Scott sent word to New York and police superintendent John Kennedy was posted to the case, unknown to Pinkerton. Kennedy also doubted Kane’s loyalty and dispatched three undercover detectives to Baltimore. Like Pinkerton’s team, they infiltrated Baltimore secret societies and believed a plot was in place. With Lincoln due in Baltimore in two days time, Scott asked Senator Seward to convince Lincoln to change his plans. Seward sent his son Fred to find Lincoln in Philadelphia, while Pinkerton was on the same mission.
Pinkerton met railroad boss Felton in Philadelphia and told him about the weight of evidence. They agreed that Lincoln needed to pass through Baltimore secretly a day earlier than planned. That day, Lincoln arrived in Philadelphia to enthusiastic crowds. Pinkerton met Judd to appeal for Lincoln to leave on the 11pm train that night. But Judd and Pinkerton could not see Lincoln until almost 10:30pm. Lincoln refused to go. The following day he was due to celebrate George Washington’s birthday at Independence Hall before visiting the state legislature at Harrisburg. If Pinkerton found new information, he might be persuaded to go to Washington directly from Harrisburg. When Lincoln went back to his room, he found a similar request from Fred Seward. Lincoln told Seward about the Pinkerton meeting, and asked if he got his information from a different source. Lincoln said he would make a decision the following morning. Pinkerton worked through the night to revise the timetable with station changes in Philadelphia and Baltimore and the added complication of the four-hour detour to Harrisburg.
The following morning, Lincoln kept his appointment at Independence Hall and paid tribute to the Founding Fathers. “I would rather be assassinated on this spot than surrender it,” he said, few realising how ominous the words were. Afterwards Lincoln told Judd he would follow their plan once finished in Harrisburg. He left for Pennsylvania’s state capital at 9:30am.
In Harrisburg Lincoln spoke at Pennsylvania’s general assembly. He met governor Andrew Curtin, and told him of the plot. Afterwards the full travelling party met in secret to discuss the plan. Senior military officer Colonel Edwin Sumner called it a “damned piece of cowardice” and wanted to bring in cavalry. But that would cause further delays. Lincoln said that unless there were other reasons besides fear of ridicule, he would carry out Pinkerton’s plan. However there was only room for one person to accompany Lincoln in the revised plan. Sumner and Lamon both believed they should be the one.
After dinner Lincoln sneaked out the Governor’s back door draped in a shawl. Lamon followed him into a carriage and as Sumner prepared to board, Lamon gave the signal to go, leaving the hoodwinked colonel behind. Incognito, Lamon and Lincoln boarded the 11pm train to Philadelphia and sat in the dark alongside a fake package Pinkerton put on board with the instructions it must go through to Washington. This would help ensure the connection would wait for the Harrisburg train. Pinkerton anxiously awaited their arrival in Philadelphia in the dead of night. He gave himself the codeword of “Plums” while Lincoln’s undignified name was “Nuts”. The plan called for Lincoln’s sleeper car to be unhitched and pulled to the other station for the second leg to Baltimore but the train arrived early in Philadelphia. Rather than wait around, “Plums” commandeered a carriage, while “Nuts”, masked by his shawl, was guarded by the armed Lamon. The carriage meandered around Philadelphia’s outskirts until it was time to board the train to Baltimore. Washington was still four hours away. Kate Warne was aboard and had secured the rear half of the final car, encouraging Lincoln to remain out of sight in a berth behind drapes. Pinkerton gave the conductor the tickets, claiming the “sick man” had retired for the evening. They anxiously crossed the Havre de Grace bridge, which was lined by Pinkerton’s signalling watchmen. They arrived in Baltimore at 3:30am.
Warne left them at Baltimore, no longer needed as “the sister of the invalid”. Railroadmen hitched the carriage to a team of horses which took it to the station for Washington, a mile away. The unaware city, thought a relieved Pinkerton, “was in profound repose”. Then they were delayed by a late arriving train. They remained stuck in Baltimore as dawn broke. Pinkerton worried the disguise would fail in daylight. Finally they got under way for the last 38 miles to the capital.
Waiting at Washington’s station was Lincoln’s old friend Illinois Congressman Elihu Washbourne. The apprehensive Washbourne thought Lincoln missed the train until he saw three stragglers in the last carriage and recognised Lincoln’s “long, lank form”. He reached forward saying, “Abe, you can’t play that on me” but an alarmed Pinkerton pushed him back. As he was about to lash out again, Lincoln cried “Don’t strike him, Allan! It is Washbourne.” Pinkerton backed off and sent a telegram to Felton that “Plums arrived here with Nuts”.
Fruity nicknames aside, it was Pinkerton’s finest hour. But Stashhower writes that the Washbourne incident was a portent of things to come. Pinkerton and Lamon, both haughty men, had fallen out over how best to protect Lincoln. Now Pinkerton had assaulted an important congressman. He also argued with the even more influential Senator Seward over Scott’s plan to send troops to Baltimore had Lincoln not agreed to the early departure. Pinkerton’s cover was blown in reports of activities in Baltimore headed by “a gentleman of Vidocquean repute”. And Lincoln suffered, with newspapers dismissing the plot as fanciful and suggesting he skulked into Washington in cowardly fashion. Lincoln’s precautions were vindicated a month later when war broke out and northern troops were killed as they passed through Baltimore.
When George McClellan took command of the Army of the Potomac in July, Pinkerton became his old friend’s chief of intelligence. Operating as “Major E.J. Allan”, he adapted his civilian skills and operatives went behind enemy lines reporting on troop and artillery movements. He exposed Washington socialite Rose Greenhow as a spy though his own man Webster was hanged in Richmond as an enemy spy. Pinkerton even conducted aerial reconnaissance using 15-year-old son William to scout enemy positions from a hot air balloon.
But McCllellan failed to press Union advantage, using Pinkerton’s information of inflated enemy numbers as excuse for inaction. Pinkerton’s reports were flawed but McClellan needed little excuse to exaggerate the size of the Rebel army. As McClellan’s reputation suffered, so did Pinkerton’s. He was dismissed after McClellan’s own dismissal in late 1862 and sat out the rest of the war in Chicago. In 1867 he was stung by Superintendent Kennedy’s account of the Baltimore Plot which claimed to know nothing of Pinkerton’s connection. Though Pinkerton wrote his own account a year later, he was also offended by Ward Lamon’s unflattering recollections which appeared in 1872. Lamon found a letter in which Pinkerton had called him a “brainless, egotistical fool” and took revenge by claiming Lincoln regretted the midnight ride through Baltimore as the danger was “purely imaginary”. Lamon said the conspiracy was a total fraud invented by Pinkerton. The flabbergasted Pinkerton decided on a new memoir but suffered a devastating stroke. Then the Chicago Fire of 1871 burned down his office, taking all his case files and records. His sons William and Robert took over the business but when an undercover operation went wrong and an eight-year-old boy was killed, Pinkerton’s tactics were reviled as barbarous and he was considered a vigilante. The harshest criticism came when Pinkerton’s men infiltrated the Molly Maguires, a shadowy group of Irish immigrants in Pennsylvania’s coalmining region whom some viewed as defenders of union rights but others saw as saboteurs, kidnappers and murderers. Several Mollies were hanged on detectives’ evidence. Pinkerton’s agency had become strikebreaking hired guns of big businesses. One critic said that the former Scottish Chartist now “preyed upon social freedom in America”.
In 1883 Pinkerton published his wartime memoirs The Spy of the Rebellion claiming he had redeemed his pledge to ensure Lincoln’s safe arrival in Washington. He believed that if Lincoln had allowed him to provide security, the 1865 assassination would not have happened. Pinkerton too was dead within 12 months after a bizarre and painful accident. Out walking, he tripped and fell, biting his tongue severely. He became infected and died three weeks later on July 1, 1884, just before his 65th birthday. His agency survived, among their number, author Dashiell Hammett. In 2003 Pinkerton’s was taken over by Swedish security services firm Securitas AB. In 2022 Securitas AB returned to his home territory when it partnered with a firm to provide an on-demand private security force in Chicago. Unblinking eye or not, Pinkerton was surely smiling in his grave.
Woolly Days 
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