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Allan Pinkerton: America’s First Private Eye

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During the Civil War, Allan Pinkerton was creating a “Secret Service,” foiling assassination attempts and rooting out Confederate spies. Jon McGinty explains how Pinkerton found his calling in the Fox Valley.

Allan Pinkerton, President Abraham Lincoln and Maj. Gen. John A. McClernand on the battlefield. (Library of Congress photo)

Allan Pinkerton, President Abraham Lincoln and Maj. Gen. John A. McClernand on the battlefield. (Library of Congress photo)

He pioneered the techniques of law enforcement before there was CSI, Sherlock Holmes, Sam Spade or even Guy Noir. Before all those, there was Allan Pinkerton.

Allan llan Pinkerton was born on July 21, 1819, in a notorious slum of Glasgow, Scotland, called the Gorbals. The youngest of seven children, only Allan and his older brother, Robert, shared the same mother, Isabelle, his father William’s second wife. When Allan was nine, William, while working as a policeman, was killed by a prisoner. Allan was forced to go to work to help support his family, but after a year as a patternmaker, he quit and apprenticed himself to a local cooper.

Pinkerton became a journeyman cooper in 1837, and worked for several years as a tramp cooper, one who travels from job to job. When he was 19, Pinkerton became involved in the Chartist movement, a political group that advocated universal suffrage for men, at a time when only wealthy landowners could vote. In 1839, he represented the coopers’ union at a Chartist convention, and that November joined a protest march on nearby Monmouth prison. The Chartist slogan, “Peaceably if we can, forcibly if we must,” was tested during a violent confrontation with police at the prison, and 22 Chartists were killed.

Pinkerton met his bride-to-be, Joan Carfrae, in 1840, and in March 1842, the couple secretly wed. Joan, only 15 at the time, lied about her age to obtain a marriage license. By this time Pinkerton was wanted by authorities concerning his Chartist activities, so on April 9, he and his new bride sailed for America to start a new life. Four weeks later, their ship was wrecked on the rocks of Sable Island, off the coast of Nova Scotia. While there, some natives robbed the survivors and took Joan’s wedding ring. She never wore another ring.

Eventually the honeymoon couple wended their way to Quebec, Montreal, Detroit and finally Chicago, where they found lodging with some Scottish friends. Pinkerton soon obtained work as a cooper at Lill’s Brewery, making beer barrels.

In the spring of 1843, Pinkerton left Chicago to start his own business in the small Scottish settlement of Dundee. On a grassy knoll overlooking the Fox River bridge, Pinkerton built a single-story log cabin with a workshop at the rear, then sent for Joan, who was still in Chicago.

“There’s a state historical marker at the site, on the corner of Main and Third streets,” says Marge Edwards, president of the Dundee Township Historical Society. “Pinkerton called himself the ‘One and Original Cooper of Dundee.’”

The business thrived, and soon Pinkerton could employ up to eight men, mostly Germans from across the river. Their newfound prosperity allowed them to send for Allan’s mother, Isabelle, and his older brother, Robert, to join them in their new home. The Pinkerton family also grew with the birth of daughter Isabelle in 1843, and son William in 1846.

In June 1846, Pinkerton’s life changed forever. While searching for raw materials for his barrels on a small river island near Algonquin, Pinkerton stumbled upon a cache of counterfeit bills and coins. He reported his find to the Kane County sheriff, who returned to the site with Pinkerton and a posse a few nights later, successfully apprehending the criminals.

“At that time, counterfeiting money was very common,” says Nancy Wendt, co-chairman of the Dundee Township Historical Society museum. “Banks everywhere printed their own money, so it was easy to produce copies.”

Pinkerton’s beliefs about social justice, which had brought him into the Chartist movement in Scotland, soon led him to become involved in the local abolitionist cause. The Pinkerton home became a “station” on the Underground Railroad, where he often gave basic instructions in carpentry and barrel-making to runaways, so they might better support themselves and their families when they reached freedom in Canada.

When Pinkerton ran for sheriff on the Anti-Slavery Liberty Party ticket in 1847, he raised the ire of some local conservative religious leaders in the local Baptist church. The minister, M.L. Wisner, accused Pinkerton of being an atheist and of “selling ardent spirits.” According to a Chicago Daily News article from 1935, a church trial was held to examine the charges, but Wisner was the defendant. When Wisner was cleared, his charges stuck and Pinkerton was asked to leave the church.

“The Baptist church is now the First United Methodist Church of West Dundee, and the building still stands on the corner of Main and Fourth streets,” says Edwards.

Pinkerton lost the election, but the pettiness of the charges led him to accept an invitation to become a deputy in Cook County. He promptly sold his business and moved his family back to Chicago, leaving Dundee for good.

The Pinkertons moved into a small clapboard house on Adams Street in the fall of 1847, and the following year Joan gave birth to twins, Joan and Robert. Another daughter, Mary, was born in 1852, but died two years later. Twin Joan died of a fever in 1855, but another daughter born that same year, also named Joan, lived to an old age. Another daughter, Belle, born in 1857, was sickly and required special care all her life.

At a time in U.S. history when bribery, corruption and lawlessness were the norm, Pinkerton quickly established a reputation as an honest, but tough, lawman. When the Chicago police force was reorganized in 1849, Pinkerton was appointed Chicago’s first detective. In one of his earliest cases, Pinkerton tracked down two kidnapped Michigan girls to Rockford, Ill., where he shot one of the kidnappers while freeing the hostages.

In 1850, Pinkerton started his own detective agency, and with partner Edward Rucker, formed the North-Western Detective Agency in a tiny office on Washington Street. When Rucker left the business a year later, Allan renamed it the Pinkerton National Detective Agency. The company’s logo was a wide-open eye, with the motto, “We Never Sleep.” It became the origin of the term “private eye.”

Pinkerton hired a small cadre of “operatives,” based more on their honesty and natural instincts than on any formal training. Their efforts were concentrated on catching criminals, gathering information, recovering stolen property and investigating fraud. Some time later, Pinkerton wrote a code of conduct for his agency that included: use no information based on suspicion rather than facts; accept no testimony from witnesses who drink alcohol; accept no cases involving divorce, marriage or political scandal.

Pinkerton also pioneered methods of investigation that are still used today. To keep track of known criminals who moved across state lines to avoid prosecution, he created a Rogue’s Gallery of mounted photographs with pertinent data on back about behavior and other details. He also perfected the use of disguises and other infiltration techniques to obtain incriminating evidence from suspects.

In 1853, an attempt by Chicago criminals to assassinate Pinkerton failed when the bullets hit his arm, instead of his back.

Pinkerton hired his first female operative, Kate Warne, in 1856, 50 years before any police department in the U.S. Only 23 at the time, Warne was instrumental in catching thieves who had stolen $40,000 from the Adams Express Company, one of the agency’s major clients. By 1860, Warne was head of the Pinkerton female detective department.

Congress passed the Fugitive Slave Law in 1850, making it a federal crime to assist runaway slaves escaping from bondage. In spite of this, the Pinkerton family continued their support of abolitionist causes, and their Chicago home became another station on the Underground Railroad. In January 1859, abolitionist leader John Brown stopped at the Pinkerton home while escorting 12 runaways on their journey north. Pinkerton raised $500 among his abolitionist friends to help Brown continue his journey. As the party of fugitives boarded a train, Pinkerton said to his young son, William: “Look well upon that man. He is greater than Napoleon and just as great as George Washington.” That October, Brown conducted his infamous raid on the federal arsenal at Harper’s Ferry, and by December was convicted and hanged for his crime.

The Pinkerton Agency did much work for railroads during this time, and through their connection with the Illinois Central Railroad, Pinkerton met two men who would have a great influence on his life: George McClellan, then president of the railroad, and Abraham Lincoln, the railroad attorney.

After Lincoln became president in 1860, Pinkerton opened a branch office in Baltimore to gather information on Southern plans to isolate Washington, D.C. In February 1861, Pinkerton learned of a plot to assassinate the new president as he traveled to the Capitol for his inauguration. At Pinkerton’s insistence, Lincoln agreed to wear a disguise and take an alternative train and route into the city. When the mission was successfully accomplished, Pinkerton’s coded message to other operatives read: “Plums [Pinkerton] arrived here with nuts [Lincoln] – all right.”

Shortly after the Civil War erupted in April, Pinkerton offered the use of himself and his agents to the U.S. military as a “secret service” of spies. When he received no reply from the government, Pinkerton left for Chicago.

McClellan, now an army general, hired Pinkerton and company to spy for his Department of the Ohio. Pinkerton promptly set up a headquarters in Cincinnati and, using the alias Maj. E.J. Allen, organized a network of spies. When McClellan was appointed Commander of the Army of the Potomac in July 1861, Pinkerton and his operatives accompanied the general to Washington, to create the U.S. Intelligence Service, an intelligence-gathering operation.

While in Washington, Pinkerton (posing as Maj. Allen) helped to uncover a large Confederate spy ring, run by Washington socialite Rose Greenhow. Once, while spying on Greenhow’s rendezvous with a Union officer, Pinkerton was discovered and briefly imprisoned by Union soldiers, unaware of his real role as an operative for the Union Army. Greenhow was eventually arrested and convicted of spying, but later paroled to the Confederacy in a prisoner exchange.

Much has been written about McClellan’s leadership during the Civil War, and much of it focuses on his apparent reluctance to decisively engage and destroy Confederate forces when the opportunity arose. That was apparently Lincoln’s concern when he sacked McClellan in November 1862. Some historians attribute McClellan’s failures to his habit of overestimating the size of the army opposing him, but some blame Pinkerton and his agency for this failure, since they were responsible for gathering such information.

Pinkerton often risked life and limb to obtain information for McClellan’s army. In September 1862, for example, during the Battle of Antietam, the deadliest day in U.S. military history, Pinkerton’s horse was shot out from under him as he tried to cross a stream.

When McClellan was removed from his command, Pinkerton resigned as head of the U.S. Intelligence Service, the precursor of the Secret Service. He returned to Chicago to focus on the work of his own detective agency.

Pinkerton’s sickly daughter, Belle, died in 1863. People close to the family noted that he was never the same again. The Civil War ended in April 1865, and a few days later President Lincoln was assassinated. When Pinkerton heard the news, he said he wished he had been in Washington to prevent it.

By 1866, both Pinkerton sons, William and Robert, had joined the family business. That same year, the agency was hired by the Adams Express Agency to apprehend the Reno gang, the first of many train-robbing gangs. Pinkerton operatives eventually captured John Reno and others, but the criminals escaped. When they were caught again, enraged local vigilantes broke into the jail and hanged the outlaws.

Kate Warne, Pinkerton’s first female operative, became ill and died in 1868. She was buried in the Pinkerton family plot in Graceland Cemetery in Chicago, where Allan would join her in 1884. Allan’s older brother, Robert, also died in 1868, but he is buried in Dundee, where he lived at the time. That same year, Pinkerton suffered a massive stroke. Although he eventually overcame much of the physical damage to his body, his writing and movements were permanently affected.

The Chicago fire in 1871 destroyed the agency’s offices, which housed most of Pinkerton’s Civil War files, and much of the Rogues’ Gallery. Despite the setback, the business was rebuilt within the year.

As part of Pinkerton’s stroke recovery, he began to develop an estate in Onarga, Ill., about 83 miles south of Chicago, on 254 acres he had purchased from the Illinois Central Railroad. Whether intended as an investment crop or just a reminder of his cooper days, Pinkerton had 85,000 larch tree saplings imported from Scotland and planted on the property. Thereafter, it became known as “The Larches.” The property eventually included gardens, greenhouses, a racetrack and fishpond, a campground and 24 buildings. The house was a villa with a cupola on top, where an armed guard could be stationed to observe the surrounding grounds. A special spur track from the railroad line allowed Pinkerton to bring distinguished guests from Chicago to his summer home.

Over the years, the estate fell into disrepair and abandonment, in spite of some local efforts to restore and maintain it as an historical site.

By the 1870s, the adventures of Pinkerton and his agents had achieved some notoriety in the public consciousness, prompting him to begin writing books and novels about his life. Altogether, Pinkerton wrote 18 books – five by himself and the rest with the help of a ghost writer.

During the early 1870s, the Pinkerton Agency was hired to bring Jesse James and the James/Younger gang to justice. Agent John Whicher tried to infiltrate the gang, but was found out and murdered in 1874. Shortly thereafter, agents were involved in a shootout, killing John Younger but losing one of their own. Several months later, Pinkerton’s men surrounded the gang’s hideout, a log cabin in Missouri. While accounts differ, most versions agree that the agents threw a smoke bomb into the cabin to drive them out. Inside, someone kicked the bomb into the fireplace, causing an explosion that killed the eight-year old James brother, Archie, and badly mangled their mother, Zelda. The James gang had already escaped into the hills.

The raid stirred up public sympathy for the gang, who were already seen as folk heroes, sometimes called the “cowboy Robin Hoods,” since their holdup victims were usually banks. For the first time in the agency’s history, Pinkerton and his agents were on the wrong side of popular opinion, but unfortunately, it wouldn’t be the last.

The Molly Maguires were a secret society of laborers who banded together in Ireland during the potato famine from 1846 to 1852. When they immigrated to the U.S., many settled in the Pennsylvania coal fields, where they continued to meet in secret. Work in the coal mines was hard, dangerous and unhealthy. When labor unrest led to violence against the coal companies, the Mollies were often blamed for the deadly encounters. In 1873, the Philadelphia and Reading Coal and Iron Company hired the Pinkerton Agency to break up the Mollie Maguire gang members, who were viewed by many miners as heroes.

Agent James McParland infiltrated the organization at great personal risk. In June 1877, McParland testified against the gang in open court; 19 members of the Mollie Maguires were convicted and hanged. The organization eventually dissolved, but in the courtroom of public opinion, Pinkerton and his agents were often seen as enemies of labor and “tools” of the companies who made the miners’ lives so unbearable.

In June 1884, Pinkerton tripped and fell on a Chicago street, biting his tongue in the process. Soon gangrene and septicemia set in, and on July 1, just 20 days before his 65th birthday, Pinkerton died. He had been in poor health for the past 15 years. His wife, Joan, died two-and-a-half years later, in January 1887.

The Pinkerton Agency stayed in the family’s hands until 1967, when it went public. By then it had 13,000 employees in 45 offices worldwide – quite a change over a century. Pinkerton’s pioneering techniques of detection, infiltration and record-keeping had been adopted by virtually every law enforcement organization in the world.

Today, the business is known as Pinkerton, a subsidiary of Securitas AB, and is still one of the largest security companies on the planet, with offices in 26 countries (including a regional office in Glasgow, Scotland, Pinkerton’s birthplace) and headquarters in Los Angeles.

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