Allan Pinkerton: Great American Detective and Spy

Allan Pinkerton was a Scottish-American detective and spy of the 1800s, and while Frenchman Eugene Francois Vidocq is often considered the French Sherlock Holmes and is known to have founded the first private detective agency in 1833, Pinkerton was no less influential in the world of spying. In fact, he established the Pinkerton National Detective Agency that still exists today as the Pinkerton Consulting and Investigations.


Allan Pinkerton

Allan Pinkerton. Courtesy of Wikipedia.

Pinkerton was born in Glasgow, Scotland in 1819 to a policeman who could no longer work because of an on-the-job injury. This left the family practically penniless and so the young Pinkerton took care of them by working as an apprentice barrel maker. He also joined the Chartists, a political movement for universal suffrage and better working conditions. Unfortunately, he found himself in trouble with local authorities because of it, and, in 1842, the same year that Madame Tussaud published her memoirs, everything came to head for Pinkerton:

“On March 13, 1842, he was due to marry a young woman from Edinburgh, Joan Carfrae. One of his friends rushed in just as the wedding ceremony was ending and warned Pinkerton that soldiers were approaching to arrest him. Pinkerton and his new bride quickly slipped away. They hid until the following morning, when they made their way to the docks and boarded a boat bound for Canada.

As the ship neared Canada it encountered a fierce storm that drove it some 200 miles … from its intended destination of Halifax. The ship finally rammed into a rocky reef near the coast of Nova Scotia and began to sink. Pinkerton and his wife lost all of their possessions and were forced into the chilly water along with the other surviving passengers. They were able to make their way to the beach, where they were finally rescued by another ship.”[1]

Allan Pinkerton and his wife, Joan Carfrae.

Allan Pinkerton and his wife, Joan Carfrae. Courtesy of Library of Congress.

Fortunately, a Scottish friend offered the destitute Pinkerton a job as cooper working for Lill’s Brewing in Chicago, Illinois. He accepted and worked there for a few years before earning enough money to establish his own business. He then set up his barrel shop in Dundee, a rural farming area about 40 miles from Chicago filled with Scottish immigrants. It was around this same time that he got interested in criminal detective work.

It happened one day while he was wandering through the wooded groves looking for trees to make barrel staves because he was too poor to buy them. While doing so, he stumbled upon a band of counterfeiters, watched them for some time, and informed the local sheriff, who arrested them. A version of this event was later published in the Boston Globe:

“In those days of state banks and wildcat money, the country was full of counterfeiters, and the storekeepers in Dundee were frequently swindled. One day a saddler named Eaton Walker, who had just been victimized by some false bills, called Allan Pinkerton’s attention to a suspicious looking individual whom he believed to be one of the counterfeiting gang. This at once aroused the hardy young cooper, who in characteristic fashion proceeded to make the wrongs of the community his own. Disguising himself as a laboring man, he followed the stranger without arousing his suspicion and finally traced him to an island in Fox river, which ever after bore the name of the Bogus Island. This was found to be the headquarters of a gang, and all were captured with their entire outfit as result of the amateur detective’s discovery.”[2]

Allan Pinkerton was touted for his exploits and as he had proved himself “a born detective, with such rare genius for the craft and such an extraordinary personality … there was no keeping him in obscurity.”[3] In fact, in 1849, he was appointed the first police detective of Chicago, Illinois, because he had already shown great skill in catching cattle and horse thieves before his appointment. That wasn’t the only praise he received.

The Illinois Central & Rock Island Railroad were suffering from constant train robberies, and so a year later Allan Pinkerton was urged to establish a detective agency. He did so by partnering with Edward Rucker, a Chicago attorney, whom he had met at a Masonic Hall. Their agency, the North-Western Police Agency, would later become Pinkerton and Company in the 1850s.

Described as being nearly 6 foot, weighing 200 pounds, and having “no waste flesh” on his massive solid frame, Allan Pinkerton was a formidable looking man. An reporter who knew him provided even more details on his physical appearance stating:

“Strong, rugged features; that peculiar, highly color complexion that indicates a good liver; short, crisp, curly hair and beard; dark, piercing eyes that impressed me with the opinion that he was looking into rather than at me. About the mouth and eyes there was that indescribable something that tells of a resolute will, a fixed purpose and great determination.”[4]

Despite his tough exterior, Allan Pinkerton maintained a calm temperament and nature. He was said to be mild mannered and not easily aroused, but if pushed to the limit, people said he fought like a lion and was unbeatable. An example of this was alleged to have happened in the 1850s when he was serving as sheriff and found himself in the middle of 40 or 50 rioters. He ordered the leader to cease and desist, but instead of obeying the man attempted to strike Pinkerton, who caught him by the neck and used a wrestling move to hurl him several feet through the air.

Pinkerton then grabbed his arm and began dragging him to the jailhouse as the astonished rioters argued and attempted to stop him, but he swept them back with arm and kept them at bay. When he reached the jail house the jailer stood waiting to close the door as soon as Pinkerton and his prisoner went through. However, as he did, Pinkerton told the jailer to keep the door open and in minutes, the 40 or 50 rioters were inside, so that when the door closed, they realized the trap Pinkerton had set for them and they were arrested.

Another time when Allan Pinkerton was pushed to his limit it involved the editor of the Chicago Democrat named John Wentworth. He was referred to as “Long John” being 6 foot 7 inches tall. Everyone feared him because he was also considered the strongest man Illinois, which also allowed him to write whatever he wanted about whomever he wanted. Wentworth therefore decided to bully Pinkerton and wrote several unflattering articles about him. 

John Wentworth. Courtesy of Wikipedia.

One day Pinkerton met him on the street, and he told Wentworth that the next nasty article about him would result in him receiving a “thrashing.” Wentworth brushed off Pinkerton’s threat and in his next issue, he scorched Pinkerton viciously. That same day Pinkerton unintentionally met him in front of a hotel and “thrashed him within an inch of his life in the presence of a wondering crowd, and then carried him into the nearest drug store and sent for the doctor.”[5] Apparently, that the was the last time Wentworth abused Pinkerton in the press.

During Pinkerton’s career he had many interesting cases. For instance, in 1855, he solved a mail theft case, despite “mail depredations [being] the most difficult to ferret out.”[6] It involved Perry Denniston who had been working as a “piler,” a clerk whose duty was to arrange packages so that the addresses could be easily and rapidly read by the person who threw them into the proper box at the distribution table. Pinkerton was able to determine that the mail losses originated at the office where Denniston worked and then he zeroed in on Denniston as the person who was committing the thefts:

“By observing that in arranging his packages, [Denniston] fingered them a little more than was necessary, as if to judge of their contents; he [Pinkerton] therefore resolved to test him. Thursday evening, decoy packages were prepared by Pinkerton, which, with alight examination, would show that they contained money, and he placed them where they would pass through Denniston’s hands about midnight; Pinkerton introduced himself into the office secretly, and obtained a hiding place where he had a full view of all the suspected man’s movements. He saw him, in sorting the packages, take up one of the decoys, retaining it longer than usual, and when the throwers back was turned, slip it into his coat pocket.”[7]

Knowing that Denniston was the one committing the crimes, Allan Pinkerton arrested him the next morning. It happened about 6am before Denniston could even get out of bed. Pinkerton then searched the culprit’s premise and found the marked money that had been placed in the decoy package. That was not the end of the story because interestingly, a little over three months later, in July, Denniston’s brother, Theodore F. Denniston, was also caught by Pinkerton committing mail theft. (Apparently, the brothers were nephews of the postmaster and took advantage of that relationship to commit the crimes.) When Theodore was arrested, he was flabbergasted, turned pale, and tried to throw away the money he was carrying. After his arrest, The Triweekly Washington Sentinel reported:

“The officers went to his boarding house and searched his room. The search was nearly concluded without finding any trace of his crimes, when officer Pinkerton decided to search minutely, and took the pictures down from the walls. On removing the backs of several, bank bills to the amount of $3,738 were found concealed, most of which were of large denominations. … Upon being told of the recovery of the money, he [Theodore] voluntarily confessed his crimes.”[8]  

Allan Pinkerton

Allan Pinkerton. Author’s collection.

Some critics of Allan Pinkerton hoped to find some bad habit in him and although they may have searched, they were unsuccessful. He “never touched cards” and was never interested in gambling. He did however like driving and horseback riding and he was known to spend many hours in “literary work.” In fact, he produced 17 books related to his experiences as a detective, with his first book focusing on his pursuit and capture of an express robber named Nathan Maroney. According to the Boston Globe, Maroney’s case “attained almost national importance and the book had such a tremendous sale that he was encouraged and urged to write the others.”[9]

The story of Maroney began when he was suspected of stealing a $10,000 package from Adams Express Company who employed him. There was no hard evidence against Maroney and a lengthy internal investigation turned up nothing. However, a few months later when another package was stolen worth $40,000, Adams Express Company contacted Pinkerton. They wanted his help to solve the crime. Pinkerton’s book titled The Expressman and the Detective was originally published in 1874 and Pinkerton states in his book that he caught Maroney based on the following:

“I maintained, as a cardinal principle, that it is impossible for the human mind to retain a secret. All history proves that no one can hug a secret to his breast and live. Everyone must have a vent for his feelings. It is impossible to keep them always penned up.

This is especially noticeable in persons who have committed criminal acts. They always find it necessary to select someone in whom they can confide and to whom they can unburden themselves.”[10]

Maroney also had no idea the lengths his employers would go to catch him. In fact, to ensure the $40,000 was recovered they employed eight Pinkerton detectives for 10 months 24-hours a day until they trapped him. Maroney also had no idea how creative Pinkerton was when pursuing a criminal. The New Orleans Times-Picayune wrote extensively about Maroney’s theft and reported on the solving of the case by Pinkerton stating:

“The detective accomplished this with a skill and perseverance, a fertility of resources, facility of disguise, and immovable tenacity of purpose which excite, wonder as we read. The rogue and his accomplice were hunted backwards and forwards, through a circuit of thousands of miles of travel; every movement, from day to day, and every night, watched and noted. Spies were set about them in their most confidential hours; their intimates were pressed into the service against them; and finally a detective brought into contact with the rogue, under such circumstances to gain his confidence, be accepted as a counsellor, and obtain actual possession of the money in trust. If we had read such a story in the memoirs of Vidocq, we should have thought it a romantic exaggeration.”[11]  

Depiction of how Pinkerton agents might have spied. Public domain.

When the evidence was strong enough Maroney was arrested and a fictitious arrest was also made of Pinkerton’s agent, who was placed in the cell with him. Maroney then confessed the robbery to him, admitted where the money was hidden, and had his wife deliver it up to his cellmate when the cellmate was released. Maroney believed that the money was being put “safely” away until he was free and could access it. He did not learn the truth until he was confronted in court for his crimes. It was then that he realized his “bosom counsellor” was a Pinkerton detective. With all the hard evidence against Maroney, the conclusion of the trial was not surprising. Judge Shorter sentenced him to 10 years hard labor at the Alabama penitentiary.

In 1859, Pinkerton attended secret abolitionist meetings held in Chicago. In attendance was abolitionists John Brown, Frederick Douglass, John Jones, and Henry O. Wagoner. At those meetings, Jones, Wagoner, and Pinkerton helped purchase clothes and supplies for Brown, who used “John Brown’s raid on Harpers Ferry” (also known as “John Brown’s raid” or “The raid on Harpers Ferry”) in 1859 to initiate an armed slave revolt in Southern states by taking over the U.S. Virginia arsenal at Harpers Ferry. Unfortunately, for Brown his party was defeated by a company of U.S. Marines, led by First Lieutenant Israel Greene, who later left the USMC and served as an officer in the Confederate marine corps during the American Civil War.

John Brown. Courtesy of Wikipedia.

When the Civil War broke out in 1861, Allan Pinkerton served as head of the Union Intelligence Service during the first two years and prevented an alleged assassination plot against Abraham Lincoln while the President was traveling to Washington, D.C. Pinkerton’s agents also worked as undercover Confederate soldiers to gather military intelligence and Allan Pinkerton himself served as an undercover Confederate soldier using the alias Major E.J. Allen. His work ultimately led to the establishment of the Federal Secret Service.

After his work with the Union Army, Pinkerton returned to capturing train robbers, which included the Reno Gang, a group of criminals that committed robberies in the Midwestern United States. Pinkerton was also hired by the railroad to track down the infamous outlaw Jesse James, who was a bank and train robber and leader of the James–Younger Gang. Unfortunately, Pinkerton was unable to capture him, and some people contend this was his biggest failure.

Allan Pinkerton died in Chicago on 1 July 1884 at age 65 and was buried in the Graceland Cemetery in Chicago. At the time of his death, he was busy creating a system that would centralize all criminal identification records, a database that is now maintained by the Federal Bureau of Investigation. There are various stories as to what caused his death. One is that he supposedly slipped on the pavement, bit his tongue, and developed gangrene. However, some contemporary reports contend that he died either from a stroke or malaria, which he supposedly contracted during a trip to the southern states.

Allan Pinkerton

Allan Pinkerton. Courtesy of Wikipedia.

His funeral took place at his Chicago home at No. 554 West Monroe Street where a large concourse of relatives and friends paid their respects. His body was laid out in a silver-mounted coffin draped with black velvet and could be easily viewed from the home’s double parlor. Lawyer Luther Laflin Mills gave his eulogy and remarks were presented by Rev. Dr. Thomas. Of Pinkerton it was said:

“How meagre are the words of man to speak the worth of Allan Pinkerton.  ‘When that the poor have cried’ this man hath made quick answer to their needs; when the wronged sought help against power he bravely bared his arm for their defense; he recognized no distinction of society save those of merit among men; he despised all fraud and false pretense; he fought for the good and against the bad; he was not content with moral suasion, but met the social enemy with weapons.

He was tender; he was strong; he was brave; he was true. … wrap him in your bosom, great Illinois – you cannot claim him as your own. He belongs to this generation and the future; no State can claim him; his memory is the right of countries, not of States. Hero and friend, farewell!”[12]


  • [1] H. L. Wagner and T. McNeese, Spies in the Civil War (New York: Facts On File, Incorporated, 2009), p. 33–34.
  • [2] The Boston Globe, “Allan Pinkerton,” March 31, 1895, p. 29.
  • [3] Ibid.
  • [4] Detroit Free Press, “Allan Pinkerton,” August 2, 1884, p. 9.
  • [5] The Boston Globe, p. 29.
  • [6] The Triweekly Washington Sentinel, “Astounding Post Office Robbery,” July 12, 1855, p. 3.
  • [7] Alton Weekly Telegraph, “Mail Robbery,” March 22, 1855, p. 2.
  • [8] The Triweekly Washington Sentinel, p. 3.
  • [9] The Boston Globe, p. 29.
  • [10] A. Pinkerton, The Expressman and the Detective (Chicago: W. B. Keen, Cooke & Company, 1874), p. 29–30.
  • [11] The Times-Picayune, “An American Vidocq,” June 29, 1860, p. 4.
  • [12] Chicago Tribune, “Allan Pinkerton,” July 4, 1885, p. 12.

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