The masquerading con man had been busy. A few days earlier, he had visited the import firm of Lane & Read, where he bought a gun, a bowie knife, and other weapons. He paid his bill with a forged $100 check and received $40 cash in change. Before that, he had persuaded stable owners around the city to keep teams of horses at his disposal, a convenience should he need to make a quick getaway. The man’s tricks were so impressive, the press had dubbed him “Dazzle.”

ON THE HUNT for Boston’s most-wanted man, Detective Derastus Clapp was patient enough to visit every hotel in the city if he had to. A tip led him and his partner to the sprawling United States Hotel on Beach Street. Here, in the guest register, the suspect had inscribed Lieut. Taylor. The hotel owner told the detectives that the naval officer was still in his room. It was July 22, 1849, and the “hot pursuit” gleefully reported by the papers for weeks was finally about to end.


Detective Clapp in an 1857 issue of Ballou’s Pictorial.

Detectives Clapp and Charles Starkweather couldn’t afford a mistake on such a heavily scrutinized case, not with the lingering fallout from the previous year’s murder of a Boston watchman. The five men in their special department not only were the first detectives in the city, they were also the first police detectives in the United States. And if they did not prove their worth, they could be the last.

The detectives gained entry into Dazzle’s room, where he lay in bed covered in a sheet. A young woman fanned him and washed his temples with cold water. The man’s sunken eyes and dry skin reinforced her opinion that he suffered from cholera, a little-understood disease that tended to claim victims in the heat of summer. Three patients had recently died in Boston hospitals, and, weeks earlier, Detective Clapp’s 27-year-old son was reported to have succumbed to the disease in New York City. Dazzle could have read about Clapp’s loss in the Boston Daily Atlas newspaper.


Dazzle slipped his hand from under the sheets and brandished the bowie knife, then surrendered it to the detectives. He seemed resigned, directing them to the gun and some other goods, including a gold watch that he asked them to hold as collateral until he repaid what he’d spent. Hanging up were a new black coat and trousers — not yet paid for — made by the hotel’s unsuspecting tailor.

The detectives decided a doctor would have to assess how to safely move their infected suspect. They left the room, avoiding further exposure, and took the woman and the weapons with them. They summoned Jacob Bigelow, a surgeon from Massachusetts General Hospital, to examine Dazzle, and posted policemen at the hotel’s exits.

When the surgeon arrived, he found an empty bed. Dazzle had eluded the sentries and made his escape. But at least the detectives knew what he was wearing: The new suit was gone.

The detectives had hoped the newspapers would celebrate an arrest, but instead used them to spread the fugitive’s description: 5 feet 11 inches high, dark hair and eyes, slender built, swarthy complexion, dressed in black frock coat and pants, black satin vest, and black straw hat, all new.

The chase was back on.

WHEN INVESTIGATORS ENLIST secret informants or covertly track an individual’s movements or synthesize clues across a chaotic crime scene to rapidly identify suspects, they build on revolutionary and controversial methods pioneered by the first generation of American detectives and Boston’s remarkable 19th-century experiment in policing.


In 1846, only two decades after Boston’s incorporation as a city, authorities tested ways to police its nearly 140,000 citizens. Newly inaugurated Mayor Josiah Quincy Jr. had inherited a police department ill-equipped for the challenge. The city employed just 30 officers — 22 for day, eight for night — and an additional force of 150 patrolmen called “the watch.” It wasn’t nearly enough.

Officially christened the Detective Police, Boston’s newest force would soon be known by a more enigmatic name: “the shadows.”

An embarrassing low point for law enforcement came earlier that year with the exoneration of Albert Tirrell, charged with the murder of his prostitute mistress amid a circus of news coverage. Tirrell was defended imaginatively by former US senator Rufus Choate, who argued that his client strangled the woman while sleepwalking. Jurors disregarded that theory but did find that the evidence Boston police had collected was insufficient to return a guilty verdict.

In the aftermath of the Tirrell debacle, Quincy and the City Council installed a take-all-prisoners city marshal, the brash Francis Tukey, and borrowed conceptually from London to establish a class of policemen focused on investigating complex cases and infiltrating underworld activities using subterfuge. Deductive reasoning — and the blunter skills of persuasion and coercion — had the potential to impose order on the disorder. Officially christened the Detective Police, Boston’s newest force would soon be known by a more enigmatic name: “the shadows.”


Detective policing conjured negative associations from the beginning — the notion of mixing with criminals, many thought, tainted the operatives, degraded them into criminals themselves, and would give rise to more crime. The new detective would have to be “dishonest, crafty, unscrupulous, when necessary to be so,” a member of law enforcement wrote later. “He is the outgrowth of a diseased and corrupted state of things, and is, consequently, morally diseased himself.”

No wonder the most obvious candidate for the new squad at first resisted joining. Police Constable Derastus Clapp, 54 years old, had already made a name for himself as a proficient “rogue-catcher,” profiting from the wide berth granted constables to supplement their salaries by accepting reward money from private citizens. Criminals who feared hearing his deep voice utter “Come along with me” called him “Disastrous Clapp.” He had a good thing going and reason to turn up his nose at the untested detective force.

Charles Starkweather, known as “Starkie,” was a brawny, foulmouthed, ambitious 32-year-old who had been among Boston’s first paid firefighters. By that fall, Starkie and 43-year-old Alexander Hopkins were joined by two more young recruits: Benjamin Heath, a 26-year-old who had gained fame for rescuing a drowning woman, and William Eaton, a 29-year-old former restaurant worker with a solemn mien and a Quaker-style beard, who aimed to fulfill his calling to help “the needy and suffering.”


An image from an 1848 pamphlet on the life and adventures of Francis Tukey shows detectives recovering stolen money from the Public Garden.

Early successes began to boost confidence in the squad. Tukey led Starkweather and Hopkins in a midnight raid on a subterranean bowling alley in Merrimac Street, following clues that it was a front. The detectives traced counterfeit bills to eight different banks. A few days later, acting on a request from the attorney general of Maine, Hopkins discovered an order for hydrocyanic acid — cyanide — in the rubbish of an apothecary shop; it was the key evidence Maine prosecutors needed in an unsolved case of murder by poisoning. In November 1847, Tukey and Eaton followed up on a rumor about a man seen two weeks earlier digging a hole in the Public Garden, tracing the event to a time shortly after the robbery of Hews & Co. jewelers. In a dramatic moment that would be remembered for decades, the officers pulled from the earth a glass jar filled with $1,125 in cash, the exact amount stolen.

Clapp could not help but notice the attention given to his competition. He could see his lucrative investigative sideline being rendered obsolete by the burgeoning detective force. He joined the squad in early 1848, bringing the division to five officers. They were headquartered at City Hall in an office shared with Tukey.

The members of the detective police began to cultivate specialties: Eaton focused on cases of violence and threats to women, Hopkins on cases of juveniles in trouble, Heath on tracking fugitives. Bolstered by underworld connections from his constable work, the gray-haired Clapp teamed particularly well with the dogged Starkie on hunting serial criminals.

The day the city announced Clapp’s new title, a baffling heist came to light that decades later remained “one of the most famous robberies that ever occurred in the United States.” In the heart of Boston, at the corner of Washington and Milk streets, burglars had spent 24 hours meticulously and leisurely clearing Currier & Trott of approximately $15,000 worth of jewelry and cash. The only traces left by the criminals were a few tools and some of the bread and meat they had brazenly taken a break to dine on.

Working together, the detectives scrutinized the crime scene, Hopkins marveling how the thieves bored through three iron doors of the vault. Elsewhere in the city, three men who were suddenly flush with cash were overheard discussing the robbery. The detectives soon arrested the men, though evidence was so scarce that Tukey pinned his hopes on matching the food scraps at the crime scene with food at one of the men’s homes.

Whatever their involvement, it was clear none of the arrested rogues was the leader. The mastermind still roamed free.

TRAGEDY STUNNED THE POLICE DEPARTMENT in the early morning hours of April 27, 1848. A 37-year-old member of the police watch named David Esters attempted to stop two burglars fleeing a Liberty Square hardware store. One of the burglars drew a pistol and fired, the bullet penetrating Esters’s intestines and damaging his kidneys. “I am a dead man,” Esters said. He died later that day with his wife by his side. The burglars got away with one dollar.

Esters (sometimes spelled “Estes”) was the second Boston law enforcement officer ever killed in action, the first in 23 years. In response, police began to arm themselves with pistols for apparently the first time in history. The five detectives assembled with the rest of the department at Court Square for the funeral. It is easy to imagine how much they burned to tackle a case that represented their raison d’etre: to identify and track an unknown criminal, to resolve a mystery with limited clues. The unexpected obstacle was Francis Tukey.

Marshal Tukey had hustled his way to the top of the Boston police. The handsome 32-year-old widower presented himself as a native Bostonian, though he was born and raised in Portland, Maine. After finding himself embroiled in multiple legal disputes as a baker, including at least two charges of assault, he earned a law degree at Harvard, then, improbably, persuaded Mayor Quincy to name him marshal. Tukey’s power grew so much that one Bostonian warned a friend that “Tukey is mayor and aldermen” of the city. The new marshal did not let anyone get in his way, underlings included. He secured a $700 raise for himself by promising to eliminate one of his deputies. When the Herald criticized him, Tukey ordered the paper’s newsboys rounded up on ostensible licensing violations.

To the other police, the presence of a convicted criminal on the detective force marked it as a club to which they didn’t want to belong.

Tukey sidelined the detectives in the Esters case, putting the investigation in the hands of a few constables he could keep in line more easily. But they botched the job — the trail went cold, and the murderer was never found. The newspapers piled on, and not only about the Esters case. The Herald made general accusations of sloppy police work and corruption, alleging that Tukey’s celebrated recovery of stolen money buried in the Public Garden was staged and renewing accusations that he sexually assaulted women. He came close to being dismissed, but dodged that fate after receiving a flood of positive press for saving a man trapped in the ruins of a collapsed building.

As for the detectives, their lack of regular beats got them labeled the “loafer police.” Benjamin Heath was called “a miserable pimp,” and the newspapers suggested Charles Starkweather was the marshal’s “jackal.” Most damaging of all, Alexander Hopkins’s dark past was dredged up: Seventeen years before, he had been sent to prison for beating his wife. If she had died, as she almost did, he likely would have been executed. Instead, he came to represent a new breed of crime fighter.

To the other police, the presence of a convicted criminal on the detective force marked it as a club to which they didn’t want to belong. One patrolman, ordered by Starkie to break down a door, replied, “If you want any doors broken open, you will have to do it yourself.”

Detective Starkweather confronts a con man so adept the newspapers dubbed him “Dazzle.” Pat Kinsella for The Boston Globe/Pat Kinsella for The Boston Glob

BY THE TIME the cunning con artist posing as Lieutenant Taylor — or Smith or Hunter — escaped right under their noses from the United States Hotel, the detectives knew their careers could be on the chopping block that Francis Tukey had escaped. But they had a new sort of secret weapon.

At the heart of detective work was the novel decision to use other criminals as spies, informants, and bait. Over time, the detectives received reports from their new “stool-pigeon” network that Dazzle had brazenly picked up where he left off, charging 40 casks of liquor to the Navy and illegally procuring another horse and carriage. He posed as a Navy doctor, which earned him an invitation to Massachusetts General Hospital, where he watched Jacob Bigelow, the same surgeon who had been summoned to examine him at the hotel, remove a cancerous growth from a woman’s breast.

Finally, Charles Starkweather got his most promising lead. A man claiming to be a plantation owner negotiated for 40 tons of coal and for the use of a wharf to accommodate a “brig laden with cotton” from his North Carolina estate. Starkie tracked the man’s movements to a home near the Old South Meeting House, where he was boarding in the guise of a Methodist minister, even pleading with his landlord for a Bible to keep in his room.

The detective negotiated the narrow streets and chockablock buildings of Milk Street, when he spotted the tails of that stolen black frock coat trailing a tall figure. After a chase, Starkie grabbed him — Dazzle was finally in hand. In the ensuing fight, Dazzle removed a 3-inch dagger from the cuff of his sleeve. Starkie struck a blow on Dazzle’s elbow, knocking away the knife, and tackled him.

At the police office, Dazzle, whose real name was Chauncey Larkin, laughed about his crimes being a “good joke.” But he seemed less lighthearted when prosecutors secured his conviction for larceny and fraud. After throwing himself on the mercy of the court, Dazzle was sentenced to three years in state prison. The detectives must have assumed that would be the last they’d ever see of him.

THE POPULATION OF BOSTON grew by nearly half again in the 1840s, more than in any previous decade. In a city of strangers, con artists such as Dazzle could show up and prey on the public admiration for military officers. Coldblooded murderers, even of an officer of the law, could vanish without a trace. Locked doors could contain dangerous secrets a few feet away from unsuspecting neighbors (stirring controversy, the detective force amassed a collection of skeleton keys said to open any door in Boston). The Springfield Republican called Dazzle’s run of success in Boston “a rare chapter in the history of villainy in our large cities,” but the threat from a man — or woman — blended into a crowd had just begun.

Days after the capture of Dazzle, Charles Starkweather and Derastus Clapp made what seemed to be a routine arrest of a woman who had tried passing a one-dollar bill altered to a 10. She had succeeded in the same scheme in 20 other stores. Margaret O’Connor was a beautiful young opera singer from New York with a voice that “enchanted all hearers” and who, it turned out, played a part in an interstate criminal ring with the potency of a hundred Dazzles: “The most extensive association of counterfeiters and burglars, and swindlers on a sublime scale, that was ever formed in the Western world,” as one contemporary put it.

The detectives sifted through ashes in John Webster’s laboratory and studied bone fragments. Webster had murdered and dismembered Parkman, then tried to burn the evidence.

At the center of this operation were two British men with an improbable shared history. One of them, known as “Bristol Bill,” had been disowned by his wealthy English family before being hired by a locksmith to invent a pick-proof lock. After robbing a London bank unlucky enough to be secured by his lock, Bill was pursued and finally arrested by a tenacious policeman in Liverpool. Six hardening years at an Australian penal colony ended with a daring escape aboard an American whaling vessel. With New York as his latest base of operations, Bill, broad-shouldered with jet-black hair and a chameleon-like ability to disguise his appearance, formed a gang that became notorious for dozens of bold robberies.

The other key to the operation was a New York-based fence named Samuel Drury, who turned plundered goods into cash as stealthily as Bristol Bill swiped them. Drury, a former police officer in England, now owned a bank with branches in New York and Boston, allowing him to pass counterfeit and stolen money on an unprecedented scale.

One of Bill’s mistresses set up the first meeting between the criminal titans at Drury’s Long Island mansion. Drury, a one-armed man, looked familiar to Bill, who stopped their conversation. “By God,” he exclaimed, “you are the hound that tracked me to Liverpool, and had me pinched.” Drury had put his law-enforcement history far behind him, however, and the two men agreed to lay aside old enmities and combine forces in the service of massive profits.

Part of the agenda: expanding the crime ring’s reach into Boston, with an audacious plan to rob the Currier & Trott jewelry store. In casing the downtown shop, Bill noticed that it was left unattended on weekends. On a Saturday evening, he sent one accomplice through the cellar to unlock the front door. With a confederate posted outside, Bill and his companions freely went in and out for the next day, unhurriedly selecting the goods of greatest value and hiding some away for transport to Drury.

Meanwhile, in New York, Drury was making a potentially deadly decision. After losing faith in Thomas Warner, one of the lawyers he employed to defend members of his ring, Drury ordered his son to kill the man and his family. Drury’s son darkened his skin to disguise himself and delivered a small tin box marked “confidential” to a servant at the Warner home. Warner lifted the lid and saw a bright blue flame — it was the fuse of a bomb called a torpedo box. He rushed his family outside just as a massive explosion knocked down a wall and sent shattered glass into the street. People across the city heard the blast. The Warner family was safe, at least for now.

Back in Boston, Margaret O’Connor, who would have passed Dazzle in the courtroom as they went in and out of their respective hearings, found herself awaiting trial for passing counterfeit bills. She turned heads in court, showing up in silks, satins, and gold drop earrings, just as she distracted merchants during scams.

At her hearing, Clapp said that O’Connor was merely a pawn for a more sophisticated criminal. There were signs that she had unseen allies. A well-respected lawyer showed up to represent her. And while officers escorted her from the courthouse to return to jail, a man with a thick beard took her arm and tried to steer her away. The police blocked the sleight-of-hand escape attempt, and the man slipped away.

A circa 1851 pamphlet on master criminal “Bristol Bill.”

The man was Bristol Bill, who had been attending her court hearings disguised by a false beard. He found O’Connor’s detention unbearable — she was the latest of his mistresses, and some believed they had secretly married. Bill pleaded with Drury for money for her bail. Drury, however, refused to “give one cent.” Bill wouldn’t forget the insult — he prided himself on his loyalty, but “there was no vengeance too terrible” when he felt betrayed — and he resolved to secure the release of O’Connor himself, no matter how long it took.

One night, Bill climbed a rope ladder over a wall of the jail holding his paramour, slipped by the sentry, and took a wax impression of the lock at the main door. He climbed back over the wall and produced a key from a wax mold. He then returned to the jail yard, unlocked the door, and took an impression of the next lock. He patiently repeated the process several times, sometimes narrowly escaping guards, until he had enough homemade keys to reach O’Connor’s cell. (“We have known of criminals endeavoring to break out of Leverett street jail,” one journalist wrote later, “but this is the only instance . . . of a burglar attempting to force his way in.”)

Though not yet aware of the prison-break plans, Detectives Clapp and Starkie put a tail on the bearded man from the courthouse — a cat-and-mouse game of evasive turns and doubling back that eventually led them to a house on Essex Place. Placing the property under surveillance, the detectives discovered it was a brothel operated by O’Connor’s brother. Raiding the home with Benjamin Heath, they found Bristol Bill, the best-known robber of his time, lying in bed. Near him sat a loaded pistol, and a trunk of customized tools, including “knives, saws, skeleton keys, punchers, augurs, gimlets, screwdrivers, crowbars, files, in all their variety,” as well as an elaborate device that may have been the one that so impressively cut into the Currier & Trott vault.

Bill, known for keeping his cool, politely asked for permission to get dressed. He commented to Clapp that in his trunk were “merely his tools,” innocuous things, and he hoped they would not be taken from him. Clapp also found the impressions taken from the keyhole in O’Connor’s cell door, which Bill had planned to use during his next visit to the jail. The arrest made headlines around the country and attracted crowds to the marshal’s office to see the noted criminal in person.

And yet Bristol Bill was soon allowed to go free, for reasons that expose the blurring lines between the new detectives and the criminals they hunted. The detectives found this the ideal opening to flip Bristol Bill, to turn a collared criminal against an even bigger target. Clapp, Starkie, and their colleagues secretly arranged with Bill to entrap Samuel Drury, whose background as an officer of the law-turned-outlaw made him the ultimate adversary. In addition to agreeing to drop the long list of potential charges against Bill , it’s likely that Francis Tukey also agreed to amend the charges against O’Connor.

There were many ways the arrangement could go south. Suspicions cropped up publicly about what the detectives were planning, with some beginning to think of Bristol Bill as “the assistant chief of the Boston police.” In Drury, they set their sights on a dangerous man with dangerous accomplices. Starkie’s home, which he shared with his wife and four daughters, was ransacked and robbed. It seemed like a message.

The detectives eavesdrop on Bristol Bill, “One-Eyed Thompson,” and criminal mastermind Samuel Drury. Pat Kinsella for The Boston Globe

The detectives entered their biggest operation at less than full strength. Tukey was dealing with a death in his family and William Eaton had been so severely beaten while making an arrest that doctors feared for his life. Though the covert arrangements would obscure the exact choreography, Clapp, Starkie, and Bristol Bill traveled to New York. Taking over a space at 23 Fulton Street in Brooklyn, they staged it to look like Bill’s current hide-out. The detectives went undercover and shadowed Drury. Finally, Bristol Bill and “One-Eyed Thompson,” another colorfully-named member of the crime ring, connected with Drury and arranged to meet.

On the appointed morning, the detectives listened from an adjoining room through holes they’d bored in the wall and artfully concealed. They wore rubber shoes so they would not be heard when they walked and held handkerchiefs to stifle coughs.

Bill and One-Eyed Thompson ably played off each other, with Bill accusing Thompson of sending the torpedo box to the lawyer’s home. If Drury had suspected Bill was working with police, Bill’s performance allayed any fears. Drury admitted that he, in fact, had ordered the delivery of the box. He encouraged his collaborators to plant another one with triple the amount of gunpowder; that should be enough to finish the job. “If we three stick together,” Drury promised, “all hell can’t catch us.”

The confession was all the investigators needed. The Boston detectives coordinated with New York officers, who rushed to a justice to get arrest warrants. When they caught up with Drury in Brooklyn Heights, he was holding several counterfeit bills identical to those passed by Margaret O’Connor. A later search of Drury’s storage space uncovered gold watches likely taken from Currier & Trott in Boston.

THE ANTI-FRANCIS TUKEY REPORTERS at the Herald could not argue with rival Boston newspaper the Daily Atlas that the arrest of Samuel Drury was “the most important one which has been made for years.” The detectives had so effectively deployed aspects of their new tradecraft — using criminal informants, making extralegal arrangements, conducting unauthorized surveillance— that detection began to seem “some magic art, some superhuman power.”

Those powers would soon be tested when a member of the Beacon Hill elite, Dr. George Parkman, vanished. During an investigation watched by the eyes of the world, professor John Webster of Harvard Medical School, who owed Parkman money, admitted to having met his creditor at the school. The detectives sifted through ashes in Webster’s laboratory and studied bone fragments discovered by a Harvard janitor. Webster had murdered and dismembered Parkman, then tried to burn the evidence. “Dr. Webster,” Derastus Clapp declared, “you are in custody for the murder of the doctor!” (Years later on a visit to Boston, Charles Dickens eagerly requested to tour the scene of the crime.)

Drury spent years tied up in criminal proceedings yet evaded conviction on any serious charge, perhaps in part by stealing important papers from a New York district attorney. Soon after testifying against him, Margaret O’Connor died of illness in the hospital of Boston’s House of Correction. One-Eyed Thompson committed suicide after beginning his own prison sentence. And even though Bristol Bill was free to go where he pleased, he did not target Boston in his future robberies. To keep track of potential suspects, the detective force established innovative secret files on criminals and kept up telegraphic communications with other police departments.

So when a veteran celebrity of the criminal class returned to town in 1862, it took only hours for him to be recognized and taken to the police station for questioning.

In the 13 years since his previous arrest in Boston, Dazzle had promoted himself from lieutenant to colonel. Wearing a uniform, and often a sling to suggest a war injury, he had defrauded various firms in the Northeast as he supposedly armed his cavalry regiment. This time, there would be nowhere for Dazzle to hide.

At the police station, there were still a few members of the old guard, including Benjamin Heath, now in his early 40s, and 69-year-old Derastus Clapp, who remained anchors of the detective squad. Tukey, removed from his post by a new mayor, had gone west to enter politics, William Eaton returned to the restaurant industry, and Alexander Hopkins switched to an administrative role in city government. Charles Starkweather, after being forced out of the department, had died in 1851, on his way to California to pursue his fortune in the gold rush.

As Dazzle was escorted out, he became sentimental. Noting the date was April 1, he said, “This is All-Fool’s Day, and I am a large stockholder.” His eyes misted as he took his leave from those officers who had pursued him as the original police shadows.

Matthew Pearl is the Cambridge-based author of five novels, including “The Dante Club” and, most recently, “The Last Bookaneer.” Send comments to magazine@globe.com.

This story has been updated to correct an error about the location of evidence found in the murder of Dr. George Parkman.