Pinkerton and the Smartest Criminal in History


Most have heard of the Pinkerton National Detective Agency from their investigations and actions taken during the latter 1800’s and early 1900’s. The Pinkertons actually filled the void between vigilante action and official law enforcement. You could say they augmented the investigations of local law enforcement which was typically much understaffed. Most of their investigations were at the behest of railroads, banks and large commercial interests who required their investigative expertise.

Crime Museum / Washington D.C.

Before we detail a very interesting old Pinkerton investigation carried out, one you’ll enjoy reading, we want to make a mention about one of the newer museum attractions in our nation’s capital.

The Crime Museum in Washington D.C. is a must stop for anyone wishing to learn more about how crime was fought and investigated over the previous decades and centuries. Visiting the Crime Museum, a very unique venue indeed, is a learning experience. You’ll see some amazing exhibits and view information about crime and justice.

The museum’s stated goal is to provide guests of all ages with memorable insight into our nation’s history of crime and its consequences, law enforcement, forensic science, and crime scene investigation through a captivating, interactive, entertaining, and educational experience.

The Crime Museum is located at 575 7th St. NW | Washington , D.C

Pinkerton and the Adam Worth Case…The Smartest Criminal In History

The case of a man named Adam Worth, sometimes spelled W-I-R-T-H, is an amazing story of non-violent thievery along with an incredible tale of a relationship developed between he and the Pinkerton National Detective Agency.

Adam Worth

Worth was born in 1844 in Germany and moved to Cambridge Massachusetts at five years of age. He grew up in poverty and decided early on to make himself rich. During his criminal years, Adam Worth worked out of London England and to some extent New York. London however was where Worth owned mansions and had stature in the late 1800’s as an independently wealthy Victorian era gentleman. Something he could never hope to attain in America.

It Was All About Money

The life of Adam Worth was a textbook case of moving up the ranks in the criminal underworld. From being a penniless crook he moved up to be tremendously wealthy albeit from other people’s money.

In his heyday Worth had a mansion, a steam yacht, a fast sailing yacht as well as all the attire of a typical Victorian era English gentleman. One robbery led to another robbery and the stakes got higher every time. The amounts stolen grew larger and larger with each crime. Whether it was blowing up safes or robbing gem shipments, Adam Worth was considered the master.

Pinkertons founder Allan Pinkerton

He was the man who planned meticulously and had his associates carry out the act. He covered all bases and no solid evidence could ever be traced back to him.

Adam Worth operated in the United States and in England and on the continent for almost thirty years during the latter 1800’s. He pulled off a daring diamond robbery in South Africa.

Adam Worth was considered literally a one man crime wave by the Pinkertons, Scotland Yard and police agencies throughout western Europe. Adam Worth and his abettors kept up with advances in safe manufacturing. It seemed that whatever new foolproof safe was manufactured, Worth and his friends stayed one step ahead, developing tools and methods to blow the best safes available.

Adam Worth…A Cautionary Criminal

Adam Worth did everything in his power to both pull off a successful theft and to make certain nothing pointed in his direction. Many people who sought him out for work were turned away. Perhaps the difference between Worth and other criminals before and after him was that he was very good at it. He was smart. By the same token, forensic evidence gathering in the late 1800’s was not what it is today.

Gainsborough's Duchess of Devonshire

Adam Worth was noted for his absolute distaste for violence of any sort. He felt that violent crime was the result of stupidity on the criminal’s part. He relied solely on brains, not brawn. Most of his crimes were planned so well and went off so cleanly that, in effect, he left his signature which the police and detectives. The law however could do little about it because of lack of evidence. This is a good example...the Pinkertons trailed Worth for some thirty years and never made an arrest.





The Biggest Adam Worth Theft

There is an excellent book that has been published, “The Napoleon of Crime, The Life and Times of Adam Worth, Master Thief“, by author Ben Macintyre. It’s a terrific read including some very interesting facts regarding William Pinkerton and his relationship with Worth. The book offers a lot of insight into both the Pinkerton National Detective Agency and Scotland Yard. You may be surprised at some of the events depicted in the book. It’s an eye opening description of the art of 1800’s crime.

The most famous theft that Adam Worth was connected with was that of the painting,”The Duchess of Devonshire” . The painting was considered an English masterpiece from the master artist Gainsborough. The Duchess’ popularity with the British public during the latter 1700’s was somewhat similar to Princess Diana’s popularity in the latter 20th century. The theft in fact was committed by Worth personally which was very rare. Worth eventually became emotionally attached to the painting, which is a story in itself, and ended up keeping it hidden for some twenty-five years.

Historians of the literary works of Arthur Conan Doyle, the creator of the Sherlock Holmes mysteries, fairly all agree that Doyle’s character Dr. Moriarty was modeled after the Napoleon of Crime, Adam Worth. In fact, many believe that Doyle received some information on Worth from none other than William Pinkerton

The most common characteristic between the real life Adam Worth and Doyle’s Dr. Moriarty was that both were playing the role of upstanding Victorian gentlemen. Both had dual personalities which is the theme of many Victorian stories

Links to two additional articles you’ll enjoy from Trips Into History include:

Charlie Siringo, Pinkerton Detective

Mark Twain / A Journalist and Virginia City Duel


Sir Arthur Conan Doyle

The Smartest Criminal Slips Up

Even the smartest criminal mastermind of the late 1800’s can make a mistake and that was the case with Adam Worth. Most likely from a combination of boredom and depression from a romantic relationship gone bad, Worth became careless.

On a spur of the moment decision while on the continent heading for Switzerland, Worth along with two acquaintances tried to pull off a daylight robbery of a coach filled with money traveling between a Belgium train and a bank in Liege.

His demise came when a bystander happened to see Worth himself breaking into the strongbox aboard the coach. His lookouts failed him, the police were immediately summoned and Worth was chased down and arrested. He was caught red handed. Adam Worth broke two of his lifelong rules. Choose your associates carefully and have others do your robbing.

Worth was tried for the crime and sent to prison in Belgium. He received a seven year sentence at hard labor.

It seems that the world renown detective, William Pinkerton, had developed over the years some sort of respect for the talents of Worth while at the same time keeping tabs on him throughout Europe and North America.

Professor Moriarty. From the Sherlock Holmes story "The Final Problem",

Pinkerton’s sympathy for criminals such as Worth, much to the concern of his brother Robert Pinkerton, was a story not entirely understood. Perhaps some of it had to do with the fact that Worth wouldn’t tolerate violence. Perhaps it had to do with Pinkerton’s heritage as compared to Worth’s childhood poverty. In any respect, William Pinkerton failed to send the Belgium authorities requested information they had on Worth.

William Pinkerton Does Adam Worth a Big Favor
The story is quite interesting in that had William Pinkerton forwarded to the Belgium authorities, as they had requested, all information on an Adam Worth, aka Henry Raymond, Worth would have received more prison time and additional charges from Scotland Yard. Pinkerton did not forward the requested information as a personal favor to Adam Worth.

It’s a good subject to explore further. When Adam Worth later met with Pinkerton at his offices in Chicago in 1901 to ask for the detectives aid in arranging the return of the Duchess of Devonshire masterpiece, he could have been arrested on the spot. He wasn’t. He came back for more discussions with William Pinkerton the next day,and during these discussions regarding the masterpiece portrait, Worth essentially confessed personally to Pinkerton for thirty years of criminal activity. The Pinkerton’s would never arrest Adam Worth.

The Gainsborough is Returned

In the end, Adam Worth successfully returned (through intermediaries) the Gainsborough masterpiece to it’s rightful owners in London.

It could not have happened without the aid of William Pinkerton, probably Worth’s only friend near the end of his life. Worth ended up with about $25,000 in exchange for the portrait. He needed the money desperately to support his two young children from a previous long relationship. Adam Worth died peacefully at his home with his children present on January 8, 1902.

(Photos and images from the public domain)


Pinkerton Detective / Charlie Siringo

Trips Into History explores the old west and in particular a Pinkerton operative of the late 1800’s. A name that may not come up as often as it should is that of Charlie Siringo.Charlie Siringo was involved in old west law enforcement as much or maybe more than familiar names such as Pat Garrett, Wyatt Earp and Bill Tilghman.

Charlie Siringo while Charlie Siringo gained much of his fame, and spent twenty-two years at it, as a detective for the Pinkerton National Detective Agency. This was the detective agency started in the mid 1800’s by Allan Pinkerton, a one time bodyguard for Abraham Lincoln, that some called “America’s Scotland Yard“. It has been written that Pinkerton had as many as 2,000 detectives on the payroll and some 30,000 in reserve. This was a total larger than the U.S. standing army during the era.

pinkerton detective agencyCharlie Siringo was a onetime Texas cowboy, a Pinkerton detective and the author of some thirty books. Many would say that Charlie Siringo molded the cowboy image as it applied to private detective work. He worked largely in the era where a Pinkerton operative acted as a sort of quasi-lawman.

From Cowboy to Detective

Charlie Siringo who was born in south Texas was looking for adventure. He moved to Chicago and because he could furnish several good references, one reportedly being from none other than Pat Garrett, Charlie Siringo was able to get a job with the Pinkertons in 1886.  His hiring was also brought along by the fact that the Pinkertons were in the market for a “cowboy detective“. Western cattle ranches were in their heyday and the Pinkertons were busy. This was fine with Siringo since he had little interest in working in the east. He was destined to be assigned to Pinkertons Denver office.

charlie siringo

Charlie Siringo, circa 1890

Before that occurred however, Siringo would find himself involved with the Haymarket Riots in Chicago. What is referred to as the Haymarket Riots was a lethal labor altercation with anarchist overtones. It ignited with a bombiing that killed Chicago policeman. This was one of Chicago’s largest labor disputes only to be eclipsed by the violent Pullman Strike during the 1890’s financial depression.

Eventually Charlie Siringo did make his way west with the Pinkertons working out of their Denver office as an “operative“. That was the term used to describe the Pinkerton detectives. Back again in the west, Siringo was put to work in a variety of the things.

Chasing Rustlers, Thieves  and Outlaws

Siringo was said to have worked for the Pinkertons as far south as Mexico and as far north as Alaska. This must have worked well for the man that disliked desk jobs. It’s also been noted that Charlie Siringo worked undercover a good deal which was something fairly unique for the late 1800’s.

wild bunch gang

Wild Bunch Gang photo. Kid Curry (Harvey Logan) is standing on the right.

Siringo was present in Dodge City Kansas when Wyatt Earp allegedly had his confrontation with Clay Allison. Charlie Siringo also provided the information for the capture of the wanted outlaw Kid Curry whose real name was Harvey Logan and was a member of the infamous “Wild Bunch Gang“.

Siringo also did work for the Pinkertons on behalf of the railroads. The railroads were big customers of the Pinkertons. One case involved theft from a railroad in Texas. Siringo’s work on this case covered both Texas and across the border into Mexico. The case was solved when Charlie Siringo found the guilty culprits to be the railroad’s own general manager along with some of the passenger conductors. This most likely was another undercover operation that Siringo proved so good at.

The Bloody and Violent Coeur d’ Alene Strike

Probably because of his experience with the Haymarket Riots in Chicago, Charlie Siringo was trying hard not to get involved with his company’s assignments in Idaho on behalf of  mine owners. He had been working in Denver at the time doing what he referred to as ” city work“. His preference was to work out in the open. Away from the office. City work was much more confining. Working out in the open let Siringo escape the heavy oversight of the Pinkerton office. The labor unrest in Idaho would eventually allow Siringo get out of the office. Charlie Siringo probably thought this was both good and bad.

During the national financial downturn of the early 1890’s, Idaho miners wages were cut and strikes and violence soon erupted. It’s important to note that just about every labor dispute in the late 1800’s and early 1900’s had to do with cut wages and hours. Unionizing was in full swing. The Pinkertons were hired by the mine owners to try to infiltrate the union and learn of their plans.

Charlie Siringo, probably as a result of his Haymarket Riots experience, developed a hatred for anarchists but at the same time he was sympathetic toward miner’s grievances. In many respects he was a man in the middle. Although this was work away from the office, Siringo didn’t want this Idaho assignment. After coaxing and pressure from Pinkerton and the Mine Owners Association, he agreed to accept the assignment. His job would be to pose as a mine worker at the Gem Mine in Wallace Idaho, work alongside the miners, and try to gain as much information about union activities as he could.

wallace idaho fire

Wallace Idaho after the Great Fire of 1910. This was the location of much violence during the 1890's miners strike.

The mine owners were trying to bring scab labor in by train. The workers and union organizers became aware and were determined to stop it by any means necessary. In one instance a trainload of scab workers was on the way and the miners in Wallace Idaho were preparing for the confrontation. Siringo learned of this and was able to tip off the mine owners who then ordered the train to proceed straight through Wallace without stopping.

Charlie Siringo eventually lost his cover and was a prime target of the union. Fortunately for the mine owners and for Siringo, the U.S. military was sent in to restore order. Charlie Siringo, by request of the military, pointed out the union leaders and they were rounded up by Siringo and others. They were placed in what was called at the time the “bull pen”. It’s important to note that Siringo pointed out the union leaders who in his judgement were the troublemakers. The ones inciting the workers. Not all of the union men fit that category. By the same token he pointed out mine managers who in his judgement aggravated the situation and in some cases incited the violence. This again was an example of Siringo’s sympathy for the plight of many workingmen even though he served at the behest of the Pinkertons and the owners.

1904 Cripple Creek Colorado, the scene of early 1900's miner strikes

The outcome of the Couer d’ Alene Strike was the 1893 formation of the Western Federation of Miners which was considered a radical union operating in the Western mining states. It would be nice to think that things settled down but trouble again flared in the late 1890’s and once again U.S. troops were brought into Idaho to restore order. The federal troops didn’t leave the area until 1901. Labor unrest was still a big issue. Violent miner strikes cropped up later in Colorado during the early 1900′s and, there too, the Western Federation of Miners were the unionizing force.

See our additional Trips Into History articles on the Pinkertons and Jesse James and the early 1900’s miners strike and Mass Deportation in Bisbee Arizona.

Charlie Siringo the Author

Charlei Siringo left the employ of the Pinkertons in 1907. Just like Allan Pinkerton he decided to write about his experiences. The Pinkertons however felt that Siringo was violating their confidentiality agreement and court hearings held things up for a few years.Eventually, Charlie Siringo agreed to delete the use of the Pinkerton name in the book titles and that settled the matter.

There were basically four themes that Siringo wrote about. These were,  his youth and life as a cowboy, Billy the Kid who he had both known and chased, his twenty-two years as a Pinkerton operative, and the outlaws with whom he had come in contact with. In addition to the above, Siringo worked as an advisor in Hollywood and even had a few bit parts.

Siringo’s writings about his many years with the Pinkertons caused a bit of a stir. The Pinkerton Agency initially blocked Siringo’s writings citing the confidentiality agreement all Pinkerton operatives signed. After a few years  the two sides reached an agreement and Siringo kept the “Pinkerton” name out of his book titles.

Charlie Siringo happened to live in an era of great change. It was the last years of the frontier, the industrializing of America, and the start of a new century. Other notables that lived through this era were Annie Oakley, Buffalo Bill Cody, Theodore Roosevelt, Wyatt Earp and of course many others. What I find interesting is how these memoirs, written later in life, seem describe a time that is fascinatingly different than the twentieth century. The change during the years of about 1880 to 1915 was dramatic. According to the U.S. Census Bureau, the frontier officially ended in 1890. By the year 1910 people were starting to drive automobiles obtaining their horsepower from internal combustion engines fueled by gasoline. How times changed.

Books About and By Charlie Siringo

Among the books I’d recommend to explore more about the life of Charlie Siringo include…Charlie Siringo’s West: An Interpretive Biography by author Howard R. Lamar. Also, A Texas Cowboy by Charles A. Siringo and A Cowboy Detective: A True Story of Twenty-Two Years With A World Famous Detective Agency by Charles A. Siringo.


The Pinkertons and Jesse James

There may have been no other train and bank robber in the 1800’s who was sought more than Jesse James. In fact, at one time he most likely was at the very top of the Pinkerton National Detective Agency wanted .

The Pinkerton National Detective Agency started in business in the 1850’s and during the American Civil War was quite active on the Union side in the capacities of both protection and spying. On the other hand, Jesse James and his cohorts were very active for the Confederacy. His cohorts included such infamous names as William Quantrill and his Quantrill’s Raiders who raised havoc with killings and massacres in the volatile Missouri and Kansas area. Also included with this group of irregular Confederate guerrillas was Bloody Bill Anderson who branched off with his own group and did much the same as Quantrill.

Jesse James, most likley taken between 1876-1882

When the Civil War ended in 1865, there remained strong differences that lasted for some time. The popular story of Jesse James was that his rampage of train and bank robberies after the war was his way of continuing the southern resistance. The James and Younger gang members were acquaintances from the Civil War with strong Confederate beliefs. A lot of this thinking was stoked by sensational newspaper and magazine stories which painted the outlaw as a crusader. Some people looked at it this way. The banks and railroads were extensions of the Union.They were the establishment.  Attacking them was, in a way, attacking the Union. This thinking prevailed in many quarters even though the Confederacy was gone.

It appears that the number one apologist for the James gangs crimes was an editor at the Kansas City Times by the name of John Newman Edwards. Edwards, originally from Virginia, was a southern sympathizer both during and after the war. From his Kansas City desk, Edwards clear objective was to instill pride in ex-Confederates and help orchestrate their return to political power. In his effort to accomplish this he lionization Jesse James within his articles and editorials. This is thought to be where the Jesse James  as “Robin Hood” myth began. I have never read any stories of the James and or Younger gangs giving out any of their monetary spoils to anyone but themselves. The Robin Hood comparison may have been from the mind of an author or news editor. The myth about James played well to large numbers of people from Missouri and Kansas since that area had a good number of ex-Confederates living there.

Cole Younger as a young man

The Pinkertons place in all this was that they were under contract from both the railroads and bank associations to apprehend the outlaws. This included James, Sam Bass, Butch Cassidy and several others. While the Pinkertons often worked in concert with whatever law enforcement group had jurisdiction, this was also an era where detective agencies like the Pinkertons operated as a type of unofficial police force. They were known to take matters in their own hands if need be. There has been a lot written about the Pinkertons and their work on behalf of big business. They were frequently hired by big business interests between the 1870’s and early 1900’s to counter and or prevent labor strike violence. There were other private detective agencies also involved in this type of work.

It is believed that the first robbery by the James Younger gang occurred on February 13, 1866 when $60,000 was stolen from the Clay County Savings Association in Liberty Missouri. This was also chronicled as the first daylight bank robbery during peacetime. A seventeen year old boy was accidentally shot and killed during the gangs escape.

Two of the most reported on crimes involving Jesse James was the attempt to rob the Northfield Minnesota Bank and later in his criminal career, the Blue Cut train robbery near Independence Missouri.


Robert Newton Ford, taken between 1882-1892

The Northfield bank robbery failed. It seems that the town was aware that a bank robbeyr attempt would take place and armed and prepared a defense. This was of course unknown to the James gang which included the Younger brothers. The bank robbery attempt took place on September 6th, 1876 ( just a little over two months after Custer’s defeat at the Battle of the Little Bighorn ). The bank targeted was the First National Bank of Northfield. The robbery was a complete failure.  A firefight ensued with the towns people and the robbery was thwarted. Jesse James and his brother Frank barely escaped. The remainder of the gang ( Younger Gang ) were either killed or captured. During the robbery attempt a bank employee and bystander were killed. Cole Younger spent many years in a Minnesota prison.

The one sure thing about the Pinkertons was that once they got on your trail they didn’t let up. They were well known for this and the outlaws knew it as well. Pinkerton agents traced James and many times would be seen in towns where James had recently been to. This was the major reason that at the end of James life he was living under the assumed name of Thomas Howard. The banks and the railroads had a large bounty on his head and the Pinkertons, including Alan Pinkerton himself, was putting more and more pressure on Jesse James. There was one incident where the suspected home of Jesse James was firebombed in an effort to either capture or kill him. The tale was that the Pinkertons were heavily involved in the attack. In fact, it’s been written that Allan Pinkerton took a keen interest in the James gang as a personal vendetta of sorts. This may have been because the gang had eluded the Pinkertons for so long. The attack occurred on January 25, 1875 at the James farm. An incendiary device that was thrown inside by the Pinkerton detectives exploded. The bomb killed James’s young half-brother and blew off one of James’s mother’s arms. After the incident, Allan Pinkerton denied that the raid’s intent was to burn the house down. Apparently the Pinkertons were given some tips beforehand by Union loyalists who resided near the farm. Jesse James was not at the farm at the time.

Allan Pinkerton, circa 1861

The last crime that Jesse James was involved with was the robbery of a Chicago and Alton Railroad train in Blue Cut Missouri. Blue Cut is an area very near to Independence Missouri where the trains slowed down at the curve making them more vulnerable to robbery. The Blue Cut robbery stepped up the efforts to capture or kill James and the bounty on his head was increased.

As portrayed in the recent movie regarding Jesse James and his death, he was shot from behind in 1882 at his home by Robert Ford, a member of his gang involved in the Blue Cut train robbery. To this day there are conspiracy theorists who contend that Jesse James faked his own death and lived a long life. DNA evidence on the exhumed remains in 1995 say otherwise. There also was a man who died in Granbury Texas near Fort Worth in 1951 who, at the alleged age of 104 and on his deathbed, claimed to be Jesse James. An exhumation took place by court order on his remains in the year 2000 . DNA tests in 2000 did not match to the DNA taken from an alleged James relative. Granbury believers say there are photos and artifacts that back up their claims. They also say that their Jesse James had a grandson who was a dead ringer for the outlaw. The people of Kearney Missouri where the other Jesse James ( according to DNA testing the real Jesse James) is buried totally discount the Granbury Texas assertions.

While the Jesse James debate continues into the 21st century, today, the Pinkerton National Detective Agency is called Pinkerton Consulting and Investigations, and is a subsidiary of Securitas AB, headquartered in Stockholm Sweden.

For those traveling to St. Joseph Missouri, there is the Jesse James Home Museum displayed on the grounds of the Patee House at12th and Mitchell. This is only two blocks away from the homes original location. There is also the Jesse James Farm located on Jesse James Farm Road  Kearney, MO.

(Photos shown are in the public domain)