The Adams Express Robbery

This is the story of a robbery, a train robbery, arguably the first train robbery. It’s a heist that starts in a pool hall in Manhattan and ends on quiet Flax Hill Road in Norwalk. It’s got loyalty and betrayal, hidden treasure, clever detectives, desperate outlaws and shifty in-laws. And of course the real hero is a convenient and efficient public transport system.

Our story starts almost exactly 160 years ago, in December of 1865. The Civil War had only just ended, and a million jaded soldiers were released into a jobless economy. Massive immigration had swelled the population of New York with a generation of impoverished Irish laborers.

Manhattan itself was an island with a bustling city only at its southern tip. Head north past 14th Street and the city thinned out quickly. You would find a railroad yard on the outskirts of town at 42nd Street, then some woods, and ultimately the distant village of Harlem.

Offenders Assemble

On a cold December 20th, 1865, Martin Allen met Thomas Clark at the St. Bernard Hotel on the corner of Prince & Mercer Streets in Manhattan. Allen had a proposition to make. He told Clark about Allen’s brother-in-law James “Whistling Jim” Wells. Wells’ friend and sort of common-law brother-in-law was Gilbert “Gilly” McGloin. And Gilly’s brother-in-law, in turn, was John G. Grady. Grady, finally, was a brakeman on the New York and New Haven Railroad, and he had spotted an opportunity.

I’m not sure why Grady, McGloin, Wells and Allen couldn’t carry this off on their own, but bringing Clark into the picture really got the ball rolling. If you imagine this as a movie, Clark is definitely the leading man. He was 25 years old, born in Oswego, New York as Hermon Kenyon. He had served for two years in the 24th New York Infantry regiment in the Civil War. After his discharge he became a substitute broker, getting rich kids out of the military draft by finding men to take their place, one way or another. This was a dirty, disreputable business, and had landed Clark in jail as an accessory to the murder of one of his “recruits”. Clark escaped from jail, changed his name, and ended up in New York looking for mischief.

Martin Allen was a 24-year-old member of a crime family, quite literally. His brothers Wesley, William and Jesse were street criminals like Martin, and their brother John ran an illegal gambling den. Their brother Theodore, known as “The. Allen”, was a low-grade power broker connected to Tammany Hall politicians. Theodore owned several saloons and other shady joints, including the St. Bernard Hotel where Martin Allen spoke with Thomas Clark.

The Target

The next day, Clark met his four fellow conspirators at Lafayette Hall, a seedy pool hall and saloon on Broadway, to discuss plans. Grady the brakeman explained that the Adams Express Company delivered their valuable goods from New York to New Haven in a specially-built iron-clad freight car, which carried a number of small iron safes. The Adams Express car ran on the 8 PM express, Grady’s regular route, so that the train never stopped along the way, or at least not for long. The express car was always accompanied by a messenger, but he rode in the passenger compartment, only checking the armored car occasionally. There were two messengers who worked on alternate nights, and Grady knew that one of them, old William Moore, was prone to taking naps along the trip.

Grady showed the others a piece of soap in which he had impressed the keyhole of the lock to the Adams Express car. This seems enterprising, but it never came to anything. Worse, the soap residue was in fact noticed by company officials, who failed to follow up.

Some days later, on a night when both Grady and Moore were on duty, Clark boarded the express to size up the situation. He made his way to the smoking car, where a man was busy making a fire in the stove. Grady entered the car, slapped the man on the back, and for Clark’s benefit said “Billy Moore, you don’t know how to make a fire.” So now Clark knew who Moore was, and he could form his own opinion about his habits.

Clark spent the trip deep in thought, and hopped off at Bridgeport. He spent the night at the Atlantic Hotel and returned to New York the next morning.

The Adams Express Company

So what was the Adams Express Company, anyway? As the name suggests, it was a delivery company, one of number of companies that sprung up in the 1850s to deliver packages. American Express and Wells Fargo were also formed in this period to serve the same market need. And like those other companies, Adams Express was eventually forced out of the delivery business during World War I and became an entirely financial operation. In fact the company still exists, as Adams Funds, one of the oldest companies still traded on the NYSE.

Back in 1866, however, Adams Express Company was still delivering the goods. In addition to this sort of bulk transport in armored cars, Adams also made ordinary deliveries to homes across the country. They were widely used for making deliveries to distant soldiers during the war, on both sides of the conflict. Adams continued making deliveries for many years. In fact, forty years after these events, the residents of Roton Hill were trying to convince Adams Express to serve their growing neighborhood. But as we’ll see, maybe the company still held bad memories of Roton Hill.

The Plan

The same day that Clark returned from Bridgeport, the gang met again at Lafayette Hall. They formed a plan to break into the Adams Express car at the 42nd street depot, put the safes on heavy transport wagons, take them somewhere safe, and break them open.

Allen and Clark visited a blacksmith at Hudson and Canal Streets, and paid him $1 to fashion a large crowbar – a low-tech alternative to Grady's soap bar. Later they scoured all the hardware stores in New York, looking for a lock that resembled the one used on the Adams Express car. They found a good match in a store at Crosby and Howard. Allen and Wells went back to the same store and bought a $6 sledge hammer.

That evening, Allen hired a horse and wagon at Crowe’s livery stable. It was time.

For reasons that aren’t clear to me, the plan didn’t work. The attempt wasn’t detected, so they must not have gotten very far. The gang apparently tried this approach four more times and couldn’t make it work.

The New Plan

They needed a new plan, and what they came up with was this: Three of them would enter the armored car at the depot, and the others would board the train as passengers, careful to avoid being seen together. The passengers would get off at Harlem Bridge. The others would toss the safes out shortly after crossing the bridge, wait a bit, then pull the signal chain to stop the train. They would get off there and walk back along the tracks to meet the others and collect the loot.

Clark could see that this plan needed a few more hands. He brought in his friend Edward McGuire, known as “Fairy” because of his distinctively high-pitched voice, and asked McGuire to bring in someone else. McGuire brought in two someone-elses: John H. Hudson, and Augustus “Sleepy Gus” Tristram. Tristram would be helpful because the gang could meet up at his place after the heist. The gang was now up to eight men.

The Heist

The plan was put into motion on Saturday, January 6th, 1866, on what would turn out to be the coldest night of that winter. The gang met up at 7 PM near the 42nd Street depot. McGuire brought two carpetbags, a marlinspike (Wikipedia), and a mortising chisel. Clark had the crowbar, the replacement lock, the sledge hammer, and a dark lantern (YouTube). On an ordinary Saturday Grady would have been the brakeman on this train, but he had swapped shifts with his colleague Isaac Wallace.

Hudson, Grady, McGuire and Clark got between the armored car and the rest of the train. McGuire tried to break off the lock with the marlinspike; he wasn’t strong enough, but Grady managed it. Grady, McGuire and Clark got in the car. Hudson closed the door and put the replacement lock in the staple but not the hasp, to make it look like the door was still locked.

The other five found separate places in the passenger compartment. Less than 10 minutes after they broke into the armored car, the train started moving.

They waited until the train entered the Prospect Hill tunnel at 92nd Street, taking in their surroundings. The plan was to hop off the train shortly after Harlem Bridge, but they now saw that the communicating cord, the rope that would signal the engineer to stop, was inaccessible in this car because it ran through an iron pipe. They would have to improvise.

They found three safes, each of which weighed about 180 pounds. Once the train entered the tunnel they flipped one over and tried to break through its bottom with the sledge hammer. That didn’t work, so they drove the marlinspike into the door of the safe and pried it open. They packed its contents into one of the carpetbags and then did the same with the other safe. I should say they packed most of the contents, because investigators would later find currency and gold strewn about the floor of the armored car. They left a third safe undisturbed, possibly because they ran out of time, but perhaps because the bags they had were already full. The lesson here: always bring more shopping bags than you think you’ll need.

While this was happening, the other five conspirators had got off at Harlem Bridge as planned, and then started walking north along the tracks, expecting to run across the safes. They walked in the cold and dark about three miles up to Tremont (map), then gave up and returned to Tristram’s place.

After Harlem Bridge, the train didn’t stop until Cos Cob. The safecrackers got off there. They hid one of the bags in some lumber near the station, then walked a mile toward Stamford and hid the other bag. Grady lived in Stamford with his father, and he invited the others to stay overnight, in a barn. Clark and McGuire preferred to return to the city. The two of them hopped on a freight train heading the other way, got off at Norwalk, and then waited for the overnight train that stopped at Norwalk at 3:20 AM heading back to New York. They chatted on the platform, and Clark wrapped himself up against the bitter cold. As the train arrived they quickly separated on the platform, entered opposite ends of the passenger car, and sat apart from each other.

Once in Manhattan again, the train stopped at 120th Street. Clark and McGuire hopped off, walked over to Third Avenue, and took the horse-drawn streetcar down Third Avenue all the way to 13th Street. Along the way McGuire showed Clark a scratch he had received on his hand some time during this caper. They headed over to Tristram’s place. Allen, Hudson and Tristram were waiting for them there, and they all caught up.

The Haul

So what was in those two carpetbags? The reports varied considerably. Most of what they stole were bank notes, currency issued by individual banks, but lacking the signatures that would make them usable. They also picked up ordinary greenbacks, five-twenty bearer bonds, gold coins, gold certificates, and a few incriminating pieces of jewelry, including watches.

Reports would estimate the face value of the bank notes at $678,000, but those notes were worthless to the thieves. It appears that the practical value of everything they stole approached $200,000. There are multiple ways of looking at what that would mean in 1866, but it would be the net worth of a very wealthy person.

The Alarm

The theft was not discovered until the train arrived in New Haven shortly after 11 PM. Old Billy Moore was supposed to check on the car periodically, but he was either fooled by the replacement lock, or napping. Immediately the alarm was raised. The police as well as officials from the Adams Express Company were alerted, and telegrams were fired off in every direction.

New Haven Police Captain Treadwell Smith was notified of the theft at 12:50. Hoping to spot the criminals if they were still on the railroad line, he boarded the next train back to New York. As it happens, that next train was the return trip of the train that had just been robbed. There weren’t many passengers, and they wouldn’t expect to pick up many along the way. But everyone working on the train was aware of the robbery, and keenly alert.

The conductor on that return trip was Henry Hurlbut, who had been the conductor on the outbound run as well. There weren’t many passengers boarding the train in the middle of that cold January night, so the two men Hurlbut saw waiting for the train in Norwalk were notable. It was Hurlbut who saw them speaking, then separating before getting on the train. In light of the robbery that seemed suspicious, and he tipped off Captain Smith.

Smith followed the two men off the train at 120th, and hopped onto the rear platform of the streetcar they took downtown. He was close enough to notice McGuire showing Clark the scratch on his hand. Smith followed the two of them all the way to Tristram’s place at 76 Horatio Street.

Recovering the Loot

That evening Clark, McGuire and Tristram took the 5 PM train to Stamford. Coincidentally taking that same train were Clapp Spooner, superintendent of the Adams Express Company, and Allan Pinkerton, who ran the Pinkerton National Police and who was arguably the most famous detective in America. Pinkerton later claimed to have spotted the three well-known rogues on that trip, in part because they got off in Stamford, despite paying their fare all the way to New Haven. Pinkerton and Spooner went on to New Haven, but Pinkerton apparently had one or more of his detectives trail Clark and company.

The three thieves all checked into the Stamford House as strangers, Clark under his name (or at least his current alias), but both McGuire and Tristram gave their name as Lockwood. The robbery was already front-page news, so everyone was aware of it. Three strangers showing up at the hotel in the dead of winter might not have aroused suspicion normally, but on this particular Sunday they stood out.

Clark went to William H. Brown’s livery stable to rent a horse and wagon. Brown was perhaps as suspicious as everyone else, and insisted that Clark take a driver along with him. Clark said he planned to pick up some ladies and wouldn’t have room for a driver, so he would be happy to pay an extra $10 for the rental, or perhaps he could leave a gold watch and chain as security. Brown refused. Apparently rental vehicle agencies have always had unhelpful customer service.

Faced with this setback the three men conferred, forgetting that up until that point they had been pretending to be strangers. Suspicions were further aroused. They stayed the night in the hotel and got on their way bright and early at 6:30 in the morning. Albert Socley, the Hotel owner, was so suspicious of this trio that he followed them down to the train depot. They returned to town briefly, then back to the depot and onto a train for Norwalk.

The Tristrams of Roton Hill

After arriving in South Norwalk, the three men walked to the home of Sleepy Gus Tristram’s cousin Josiah. Gus must have been familiar with Josiah and the area in general. In fact Fairy McGuire had also spent the summer in the neighborhood two years previously, so he too was known to the Tristram family, although at that time he was going by the name of Edward Watson.

Josiah Tristram was a shoemaker. He lived in the house that still stands at 378 Flax Hill Road with his wife Annie and their daughter Ella. Josiah’s sister Emma Woolsey, a widow, lived on the upper floor with her three young children. Josiah and Emma were born in Staffordshire, England, but their father brought them to Darien as children around 1828; he still lived over on what is now Raymond Street (about here). Gus’ father came with them and also lived in Fairfield County for a time, before marrying and moving to Brooklyn.

Incidentally, there’s a historical plaque on a home on Sheffield Road for a William P. Tristram; that was Josiah’s brother, who had died a few years before these events. And while we’re here, Annie Tristram was at this time pregnant with William Henry Tristram (1866-1931), who would go on to be the popular rural mail carrier for the Rowayton area. He lived in this same house into the 1920s.

In the newspaper stories about the robbery and its aftermath, Josiah is invariably referred to as “Old Mr. Tristram.” That seems a little harsh for someone who was only 39 in 1866. I’m not sure whether “old” was meant familiarly or dismissively, or whether he just appeared physically old. Some stories do indicate he was frail.

Recovering the Loot, Part Two

Gus Tristram went off to the livery stable in Norwalk and came back with a horse, a Rockaway carriage, and Hudson. Tristram had said that he was expecting his wife to join him here for a trip to Boston, but instead Hudson came to tell him that she wasn’t able to make it. That seems like a completely normal thing.

By this time McGuire appears to have left; reports are unclear, but he doesn’t play a role in the remaining events in Norwalk. The other three crooks – Clark, Hudson and Gus Tristram – explained that they needed to fetch some luggage from Stamford, and needed to do so right now, at 8 PM. On unlit country roads. This too apparently raised no suspicions in the minds of their hosts.

They went to Cos Cob bridge to recover the two bags. The one-way journey was about 10 miles, or perhaps two hours by carriage. They finally made it back to Roton Hill about 3 AM. In Tristram’s house they repacked the heavy bags, reinforcing them with skate straps that the shoemaker must have had around the house.

These three were all well-known crooks, and they risked being stopped and searched on their way back to the city. So the next morning they convinced old Josiah to carry the loot back to Manhattan for them. Josiah was told to deliver it to Gus’ sister and Josiah’s cousin Matilda Barmore at 100 Division Street, in what is now Chinatown. They told him to take a hack from the train depot to the Barmore place, traveling in style. They would pay him $25 for his troubles.

Josiah Tristram set off for Norwalk Station, carrying a heavy bag on a hand sled. The bag kept slipping off, so a young man named Charlie Ferris, who happened to be a cashier at Norwalk Bank, helped him carry the bag to the train. Once on the train Tristram insisted on holding the bag on his lap, reportedly even refusing an offer to check it.

Tristram delivered the goods to his cousin's place and returned to Norwalk on the 11:30 AM train.

The Arrest

I don’t know whether Josiah Tristram or Emma Woolsey suspected that their guests were involved in the Adams Express robbery, but practically everyone else in the tri-state area did. One example was A. L. Hopkins, the livery stable owner in Norwalk. When Gus rented the horse and carriage from him, he became so suspicious that he sent his twenty-year-old son to follow him.

Hopkins’ son trailed Tristram to the train station when he picked up Hudson, and then when he went back to Josiah Tristram’s house. He may have trailed him all the way to Cos Cob and back, but in any case Hopkins heard enough to justify a telegram to the Adams Express Company. Of course this wasn’t just a question of being civic-minded; everyone knew there would be a reward.

By that point the company may have already known about what was happening on Roton Hill. Pinkerton later claimed that he had noticed the well-known criminals Clark, McGuire and Tristram on the train, and had detectives following them ever since. The population of Roton Hill at this point must have doubled on this Tuesday, considering the small army of people keeping a watch on the Tristram house.

One report says that a deputy was sent to the Tristram house on the pretext of buying wax, to see who was present. The deputy was told that Josiah was out and there were no strangers at home, but a nearby child said “Yes there are; they’re upstairs!”

While old Josiah was returning home, Spooner and Pinkerton were swearing out an arrest warrant. John Hudson apparently took some of the cash and left, saying he was headed for Boston. Much later the newspapers said he had escaped to Europe and was never seen again.

Spooner, Pinkerton and Sheriff Barnum, plus assorted other police officers, Adams Express employees and Pinkerton agents, finally raided the house in the early evening. Gus Tristram played innocent, claiming he didn’t know Clark at all. His story fell apart when one of the stolen watches was found on him. Josiah Tristram pleaded ignorance, and agreed to accompany Superintendent Spooner back to Manhattan to show him where he had dropped off the loot.

In the meantime Pinkerton and the other officials searched the house. They found partially burnt bank notes, the unsigned form of currency, in two of the stoves. Pinkerton had his detectives search the house and grounds nearby, and they eventually found a stash of gold hidden under a stone wall about ¾ of a mile away. Yes, that’s right, there was hidden treasure on Flax Hill Road, and maybe they found all of it. But then again, maybe they didn’t.

Meanwhile, back in New York, Spooner woke a local judge at 2 AM to have him issue a warrant to search the Barmore place at 100 Division Street. When they raided the Barmore house, Matilda Barmore swore they didn't have the money, but the officers eventually found it hidden in a flour barrel.

The Barmores were initially arrested, but then released as there wasn’t enough evidence connecting them to the actual theft. Josiah Tristram was also released. Reports at the time painted the Barmores as collaborators, but Josiah as a gullible dupe. One story said that “he has vegetated, through the whole of his staid life, in the rustic stagnation of a quiet little Connecticut village, and that he has never had an opportunity of acquiring the smartness which is forced upon the inhabitants of large cities.” Well, I’m pretty fond of our rustic stagnation.

The Trial

By the end of January, Tristram and Clark were on trial in Bridgeport for receiving stolen property. At this stage little was known about who performed the actual robbery, and it was certainly unclear whether Tristram and Clark were involved. But they were definitely in possession of the stolen goods in Norwalk, so those were the charges they faced.

Sleepy Gus Tristram immediately pled guilty, through some combination of remorse and not wanting to force his cousin Josiah Tristram and sister Matilda Barmore to testify against him. The New York Times noted that he “has a lovely young wife, who stands nobly by him with true womanly devotion in his hour of need, and two very interesting children.” Interesting children?

Thomas Clark, or whatever his name was, planned to fight it out. The New York Times described his defense team as Charles Chapman, the leading criminal lawyer in Connecticut, Mr. Walter S. Shupe of New York, Mr. Wilson of Norwalk, and Ex-Judge Sydney Harrison Stuart of New York. The notorious Judge Stuart was the primary attorney for the professional criminal in New York, and had himself been indicted for bribery when he was a city judge. The New York Times said his “name seems to be a household word in all homes of crime and trouble.” It is perhaps worth wondering exactly how Clark could afford this high-profile staff.

Facing off against them were District Attorney Carter, General Ferry, and S. B. Beardsley, plus Clarence Seward, who was acting on behalf of the Adams Express Company.

The gaggle of lawyers would fill a courtroom by themselves, but there was an overflow crowd of onlookers as well. Adding to the sense of spectacle was the presence of showman Phineas T. Barnum in the gallery for the first day of the trial. That first day was perhaps not the greatest show on Earth, because it appears to have been taken up by reading the depositions of government officials to establish that the Adams Express car was in fact carrying the notes, bonds, cash and other packages in question. Also among the witnesses was Benjamin T. Smith of Brooklyn, who identified a gold watch in a mahogany case that he had sent to his sister-in-law in Boston, and which was found in the possession of one of the thieves.

Sleepy William Moore, the Adams Company messenger, testified that he had in fact checked the armored car twice along the route, but it was dark so he didn’t see whether the padlock was on or not. More importantly, he was only able to check the left side of the car, since all the platforms at which they stopped that night were on the left. Moore had worked for the company for 18 years, but was fired after this dereliction of duty.

Also among the witnesses were Josiah Tristram, his wife Annie, and his sister Emma Woolsey. Mrs. Woolsey testified to receiving a gold watch and some money from Gus Tristram. So they weren’t spared from testifying, but at least they didn’t have to testify against their cousin.

Three separate witnesses saw the Rockaway carriage in Cos Cob. The Cos Cob bridge tender said he found a canvas bag with $5,000 in gold, plus a discarded padlock and chain, along the railroad line. The newspaper says that Pinkerton detectives had been patrolling 25 miles of railroad line to both search for stolen goods, and to shoo away treasure seekers.

Clark’s defense called witnesses to say that Clark was in New York all of the 6th and 7th. The State called rebuttal witnesses to say that others in those same places hadn’t seen him there. 

The newspapers covering the trial noted a disturbing rise in crime in this period, illustrated by the fact that when the valuable evidence of this case was sitting in an ante-room waiting to be introduced, someone tried to steal the safe it was held in.

The Verdict

The jury found Clark guilty of only the fourth count against him; I don’t know what it was. He was sentenced to five years in the State Prison, but Ex-Judge Stuart immediately filed an appeal and his sentence was put on hold. He was returned to the Bridgeport jail. 

Augustus Tristram, having pled guilty, was sentenced to three and half years in the State Prison at Wethersfield.

Further Investigation

Adams Express officials were sure there were others involved in the robbery. The company had a policy of fully prosecuting everyone involved, regardless of cost, because robberies of express shipments were on the rise, and they needed to demonstrate that it would not ultimately pay off.

The company got little help from the New York Police, or more specifically from their detective branch, who were widely seen as entirely corrupt. In fact the New York Herald reported that a New York detective had been seen lending his badge to Martin Allen before the latter visited the Barmore place, so that Pinkerton detectives would not be able to arrest him.

Pinkerton believed that James "Whistling Jim" Allen was involved in the original robbery, possibly due to the observations the agency had made of the Tristram and Barmore households. Allen lived with his mother, who ran a boarding house. Pinkerton placed a detective named James P. Hall in that house, with the intent of becoming a confidant of James Wells. Over the course of several months, from February to June, Hall did just that, telling Wells about some of his (presumably fictitious) criminal undertakings. Eventually Wells reciprocated, telling the whole story of the Adams Express robbery as a boast.

In May, the Pinkertons had the five remaining conspirators arrested: Grady, Wells, Allen, McGloin and McGuire. Originally Grady wasn’t going to be arrested. They knew he had something to do with it, but lacked enough evidence. But shortly before they issued warrants Grady was accused of robbing a passenger on his train, so they decided he should be included.

The Trial in Danbury

In this period the duties of the county seat were shared between Bridgeport and Danbury. Clark and Tristram’s trial had been in Bridgeport, but the trial of their fellow conspirators started in late August in Danbury. The prisoners were again defended by Ex-Judge Stuart.

The prosecution caused a sensation in court when they introduced their star witness, who was none other than Thomas Clark. Clark had turned on his colleagues, and at least according to the newspapers, this was somehow sprung on the defense as a surprise. Clark told the whole story in elaborate detail, just as I have described it here. Obviously most of the story came entirely from him. The story clearly paints Clark himself as guilty as all the others, but it would appear that he had negotiated his release in return for his testimony. The defense, presumably not actually taken by surprise by his appearance, attempted to discredit his testimony in part by raising his past as a substitute broker and a fugitive from a murder charge.

Pinkerton detective James P. Hall testified about his stay in Mrs. Wells’ boarding house, and about Wells’ description of the Adams Express robbery. After the trial Hall was seen being accosted outside the courthouse by actress Anna Marsden, who was in a relationship with James Wells.

The defense put on various witnesses to say that the prisoners had been doing all sorts of other things on the 6th and 7th, and thus couldn’t have been involved. Grady’s father, for example, testified that his son was home in Stamford all that night.

The jury deliberated for two hours before reporting that they could not come to a unanimous verdict. The judge sent them back, but they returned a little while later in the same state. This was therefore a mistrial, and a new trial was set for late October.

Prior Engagements

The prisoners were returned to jail, but Fairy McGuire somehow posted an $8,000 bond and was released. Shortly before his second trial in Danbury was set to begin, he was arrested in New York, and extradited to Maine to be tried for the robbery of the Bowdoinham Bank. He therefore wasn’t able to appear in Danbury, and forfeited his bail. For context, $8,000 would have bought you a house with a substantial farm.

The Second Trial in Danbury

The remaining four prisoners had a second trial in Danbury starting in late October. All the same protagonists were in place, including the prosecution and defense, aside from McGuire. The same witnesses were called, and gave the same testimony. In this trial, the prisoners were for tactical purposes charged only with stealing the gold watches and some gold certificates worth about $800 in total.

On November 2nd, 1866, Allen, Wells, McGloin and Grady were found guilty. Ex-Judge Stuart filed his usual array of delays and appeals, and the prisoners were returned to the Danbury jail.

The Escape

In the Danbury jailhouse the prisoners enjoyed the excellent hospitality and lax discipline of Sheriff Matthew Bulkley. Among other indiscretions, the Sheriff routinely allowed women to stay with prisoners overnight. On the 23rd of January, as one example, the Adams Express prisoners were joined by Eliza Allen, Mary Grady, and actress Anna Marsden, who according to the paper “was visiting Mr. Wells as a lover.” The next morning, the jailers were surprised to find that the women were all present, but the prisoners had all escaped.

The prisoners had dug under a loose floorboard in Allen’s cell, using tools that had been smuggled in among the women's underclothes. The dirt was stashed in the cell, hidden under the carpeting that was inexplicably part of the decor of the cell. The women were each in their individual cells, but the men had all been in Allen's cell when the jailer locked the doors for the evening. As usual the jailer had not checked whether everyone was in his place. The prisoners emerged in the graveyard next door to the jail, and had been gone for 10 or 12 hours before the escape was discovered.

The women were arrested and spent several months in jail, despite Ex-Judge Stuart’s claim that there was no evidence that they aided the escape, and if they did then they surely must have been coerced by the escapees.

All four robbers were all eventually captured. Martin Allen and John Grady were arrested as they prepared to roll a drunk in New York. As the officers were bringing them to the station, one of them noticed Grady fumbling with something in his pocket, which turned out to be a loaded pistol. I take it that frisking prisoners upon arrest wasn’t a thing in 1866. Shortly afterward the officer noticed that Grady was also carrying a so-called “sand club”, basically a blackjack. Allen, for his part, was carrying a set of skeleton keys, which in his hands were obviously burglar’s tools.

Allen and Grady made another attempt to escape from the Bridgeport jail, somehow acquiring a jackscrew and a log, with which they were attempting to break through the wall.

The Sentences

Sleepy Gus Tristram was sentenced to 3 ½ years in the State Prison in Wethersfield. He escaped quite near the end of that sentence, but in 1870 he was sentenced to 20 years in Sing Sing for stealing $800 worth of silverware in Brooklyn. He must not have served all of his time, because in 1882 he was again arrested for the burglary of a store in which a replacement lock was used to disguise the break-in.

John Grady was sentenced to 5 ½ years for the robbery, and another 2 years for the jailbreak.

Gilly McGloin was sentenced to 5 years for the robbery, and another 2 years for the jailbreak.

Martin Allen was sentenced to 8 ½ years, two of which were likely for the jailbreak. He didn't serve his full sentence, and immediately after he was released he went right back to a series of burglaries and robberies. In 1869, for example, he was indicted as a "panel thief", an elaborate crime in which a prostitute would lure a man to a specially-prepared room, and while his attention was occupied, Allen would quietly slide a panel open and steal his wallet. Charming. The newspapers openly doubted whether Allen could ever be brought to justice, due to the rampant corruption of the police and courts in New York. 

Edward “Fairy” McGuire served 15 years in prison in Maine for the bank robbery there, and was never convicted of the Adams Express robbery. But he was in and out of jail for the rest of his life.

I can’t find any report of James "Whistling Jim" Wells being captured after his escape from Danbury, but there are stories that say that all the escapees were eventually caught.

John H. Hudson reportedly absconded to Europe. Some reports say he was never heard from again, but others say that died shortly afterward, and in fact returned the money he had stolen via the priest who gave him last rites.

Thomas Clark was set free after turning State’s evidence on his colleagues.

So that’s the story of the Adams Express Robbery, one of the most notorious crimes of its era. And it all came to an end on Roton Hill. All we have left are the newspaper reports, the memories, and who knows, maybe just a little more of that hastily-stashed gold.

Sources

• Bucholz and the Detectives, by Allan Pinkerton, 1880. Available through Project Gutenberg. Discusses the Adams Express robbery as a digression in Chapter 18.

• Coverage of the second trial in Danbury from The New-York Tribune, October and November 1866.

• Professional Criminals of America, by Thomas Byrnes, 1886. Available through Google Books. Includes a profile and photo of Fairy McGuire, and mentions Sleepy Gus but doesn’t have a profile of him.

• A not-very-accurate retelling of the story in the Baltimore Herald Magazine, from 1956.