Pinkerton used an unblinking eye as his trademark because he was known as the Eye, since he could apparently grasp every detail of a situation or person in an instant.

Much of the confusion about Pinkerton is due to biographers taking his memoir at face value without checking the facts. Another problem is that most of Pinkerton’s records disappeared when Pinkerton HQ burned to the ground in a Chicago fire.

A journeyman cooper, Pinkerton was swept up by the Chartist movement, which was pushing for more votes and equality for the working class. He became one of the leaders who pushed for the use of violence to achieve these goals, and he led a group of men during the Newport Uprising on Nov. 4, 1839. It failed, and he left Scotland for America in 1842, along with his 15 year-old bride. The couple stayed in Montreal for a while, before moving to Chicago, which only had 1,200 people at the time. He worked 14 hours a day, 7 days a week, and had his own shop with 8 employees within 3 years.

Pinkerton’s career in law enforcement began when he helped arrest a band of counterfeiters. He had noticed the remnants of a campfire on a deserted island when looking for lumber, and spent several nights waiting for them to show up. After helping arrest another counterfeiter he became deputy sheriff, a part-time job that let him continue to run his cooperage. At the same time, the writings of Frederick Douglass convinced him to join the Underground Railroad. Pinkerton moved to Chicago when it started to boom, and he became a deputy sheriff, where he was a successful detective until his abolitionism put a damper on his career, so he quit and accepted a position as a Special United States Mail Agent for the US Post Office, but he still found time to found the North-Western Detective Agency around 1850. Although Pinkerton is credited with inventing the private detective, Eugene Vidocq in Paris had actually been first in 1832. However, Pinkerton was the first to create an agency that was not limited to county borders, and he was the first to hire female detectives. Unlike the stereotypical modern private eye, Pinkerton’s General Principles dictated that his agency would not represent defendants in criminal cases unless they had the prosecutor’s permission and that it would not investigate women for divorce proceedings.

Pinkerton met McClellan when he was chief engineer for the Illinois Central Railroad, and they became friends because they were both egotistical, nit-picking ball-busters. At the same time, his involvement with the Underground Railroad became so deep that his house was perpetually crammed with runaway slaves. He even worked with John Brown, and did everything he could to prevent Brown’s execution.

By 1860, the Pinkerton Agency was on retainer to the US Post Office, 2 express companies, and several railroads, with Pinkerton inventing criminology along the way. Acting on Samuel Felton’s instructions, Pinkerton uncovered a plot to kill newly elected President Lincoln, and his operatives guarded Lincoln’s train on its way to Washington. When the Civil War started, Pinkerton offered his agency to Lincoln, but nothing concrete happened. However, McClellan soon became the second highest ranking officer after Winfield Scott, and he asked Pinkerton to organize a secret service for the army. Washington, DC was overrun with Southern Sympathizers and spies, and Pinkerton worked hard to break the Southern spy ring headed by Rose Greenhow, Stephen Douglas’ aunt and the former mistress of James Buchanan. When he finally obtained authority to search her mansion, he found a treasure trove of evidence that resulted in arrests throughout the government. However, despite being placed in house arrest and later moved to another home, Rose continued to tempt men into spying for her. Eventually, her highly connected admirers succeeded in getting her paroled, and sent to the South.

Unfortunately, Pinkerton’s success in uncovering spy rings was not equaled in gathering information about the Confederate army. McClellan postponed his offensive because one of Pinkerton’s operatives behind enemy lines overestimated the Confederate army by a third. When McClellan lost his feud with Secretary of War Stanton (another version is that Lincoln got fed up of McClellan’s lack of desire to do what he was paid to do, namely fight), Pinkerton left government service to return to private practice. One consequence is that without Pinkerton to keep an eye on things, Lincoln’s incompetent security detail was out having a drink, enabling Booth to kill Lincoln, although there is a theory that Stanton set Lincoln up to be assassinated.

The Pinkerton Agency continued to be quite effective after the war, and solved a number of high profile cases. John Reno, head of the train robbing gang, was arrested after Pinkerton agents infiltrated his hangout, and arranged for him to be caught at a specific place. Unfortunately, his methods required so much time and manpower that some companies thought it cheaper to put up with robberies.

Unlike the Reno gang, the James-Younger gang proved much harder to catch. Pinkerton was furious that several of his agents had died investigating the gang, and none of his agents would accept the case after that. He wrote “there is no use talking, they must die,” and the James house was bombed soon after. A hard man, Pinkerton had little sympathy for the relatives of outlaws, and wrote that “the James’ mother had met with a merited and fearful punishment” when she lost her arm in the explosion. He tried to claim that the bomb thrown into the James cabin was a simple smoke bomb which exploded when thrown into the fireplace by her husband, but a smoke bomb that kills a child and takes off a woman’s arm seems like overkill to say the least. Furthermore, Marley Brant has found a record stating that Gen. Phil Sheridan allowed Pinkerton operatives to use military explosives.

Oddly enough for a man who took part in a workers’ rebellion, Pinkerton led his operatives against the Molly Maguires, viewing them as a terrorist organization that wanted to dominate both non-Irish miners and mine superintendents, even though he was aware of the incredibly harsh conditions in the mines, and Gowan, the coal-mine owner who hired him appears to have been an especially nasty example of an unscrupulous capitalist. Pinkerton’s agents successfully infiltrated the Maguires, and agent James McParland spent 2.5 years working 20 hour shifts for miserly wages as part of his cover. After a bitter strike, Pinkerton’s agents produced evidence that resulted in the hanging of 19 Maguires, while Gowan lost his company and eventually killed himself.

Pinkerton was a control freak who refused for years to let his daughter marry because he did not want her to leave him, and he only began handing over operations to his sons when he was 60.

Related Movies:

The Tall Target (1951)
Directed by Anthony Mann, starring Dick Powell and Adolphe Menjou
A discredited detective learns of a plot to assassinate Abraham Lincoln as he travels by rail through Baltimore to his inauguration.

American Outlaws (2001)
Directed by Les Mayfield, starring Colin Farrel, Scott Caan and Ali Larter
The James and Younger brothers return to their homes after the Civil War ends and find that a railroad company is trying to force farmers off their land. The young men try to organize their neighbors to oppose the company but when the James house is bombed and their mother dies, they form a gang to rob the company and the banks where it stores its money. (please click here to read the review)

Books:

Allan Pinkerton: The Eye Who Never Slept. James Mackay, Edinburgh: Mainstream Publishing Company Ltd, 1996.



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