Matthew Pearl is a sucker for underdog stories, origin stories and untold stories. Those all came together when the author of best-selling historical fiction thrillers such as “The Dante Club” and “The Poe Shadow” asked: Who were America’s first detectives?  And what did they do?

It’s a primal form of storytelling: “Let me tell you what happened right on this spot a long time ago.”

Surely, he thought, the founding sleuths would have been celebrated somewhere, their names etched into a plaque in honor of their work. Something?

Deploying his own detective work, raiding archives, ricocheting around Boston, Pearl not only tracked down the squirrelly bunch of men who were America’s first gumshoes, he scored a narrative jackpot.

Pearl’s rippin’ yarn, “Into the Shadows,” debuted in the Boston Globe Magazine in April 2016. Then this summer, Paramount Pictures announced that Ben Affleck, Matt Damon and Jennifer Todd (the trio who produced “Manchester-by-the-Sea”) were teaming up to produce “Into the Shadows” as a feature film.

So what’s it like for the writer who mainly traffics in imagination and invention to navigate the constraints of nonfiction? How far will Pearl go to satisfy his curiosity or verify a hunch? How does he sidestep sketchy holes in the narrative? Among other thoughtful answers in the annotation, Pearl points to the underexploited opportunity of historical longform, eulogizes his time wasted hunting archives for the letter “R,” and describes the counterintuitive freedom he feels writing true stories. “It’s like a free pass,” the novelist confesses with relief. “It happened!”

My questions are in red; his answers are in blue.

Into the Shadows

By Matthew Pearl

Originally published in The Boston Globe Magazine on April 28, 2016.

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. How did you decide on your lede? Did you toy with beginning the story another way? I keep a writing journal for each of my longer projects. From my journal for this one, here’s me brainstorming with myself (does that count as brainstorming?) about the lede: “I think it’s smart to start with something dramatic involving the detectives (not just a dramatic crime and then an un-dramatic arrest); or… starting with the acquittal of the wife killer, bringing up various issues… I’m not sure there’s that one dramatic scene… [later update] I think for now, at least, the plan of starting with the acquittal makes most narrative sense…” That entry continues with more false starts on possible beginnings. The “acquittal of the wife killer” refers to the Albert Tirrell case. But that case (which I end up mentioning in the second section of the piece) didn’t involve the detectives, so that should have struck me immediately as a dead end — you’d have to invest time in introducing people not featured in the article. I also toyed with narrating a different arrest by Clapp and Starkie, this one of a New York counterfeiter who escaped prison disguised as a woman, but the case itself was a one-off and couldn’t be further developed. I ended up deciding I wanted to greet the detectives mid-step during a case while not being fully successful with their methods. 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. What were you looking for when you came upon this story? Why did you start with this moment? This project grew out of not being able to find any answer to a pretty straightforward question – Who were the first police detectives, and what did they do? I searched for every scrap of information related to Boston’s first five detectives that I could find, no matter how trivial, from the day their department formed in 1846 until Thanksgiving 1849, which is when their activities started to be better documented. The failed arrest of Dazzle gave me a bundle of things I was looking for in one fell swoop—a colorful criminal, more than one detective at work, Boston as a palpable backdrop and interaction with the press. What made you feel this story had something to say about these times/how did you countenance the “why now?” question? It’s framed as, “America’s first police detectives launched a radical new approach to cracking cases.” But it’s actually more rippin’ yarn than history lesson. It’s so hard to place historical pieces today, and I believe it’s a space that’s really underexploited, for lack of a more pleasant word, within our nonfiction longform renaissance. It’s an arbitrary measure, but look at articles tagged in the history category on Longform or Longreads and you find a short list from a handful of publications. I often put aside historical ideas knowing how grueling pitching them would be. The question many editors ask of historical pieces is tougher than “why now?”; it sometimes feels more like just “why?” It’s a shame — not only because I gravitate toward those pieces as a writer, but also because readers really dive into them, far more than many outlets seem to realize. It’s a primal form of storytelling: “Let me tell you what happened right on this spot a long time ago.” I am drawn to underdog stories and origin stories (this is both!), and those stories that have been lost or never been told at all (again, this). I hoped the Boston setting would be a strong draw for the Globe Magazine, and I did weave some newsiness into my original pitch, which I’ve dug back up to share here: “When operatives went undercover to snag Whitey Bulger, the techniques and the concept of a network of secret informants can be traced back to the controversial methods of the original detectives–also known as ‘shadows.’ As local and federal operatives converted the disparate clues at the Boston Marathon bombing into the identity of a perpetrator, we witnessed a remarkable synthesis of evidence revolutionized by the pioneers of detective work, whose skills were sometimes thought magical or supernatural. In addition to the ties to today’s most challenging and captivating investigations, and to every episode of Dateline or CSI we land on while channel-flipping, there is a more basic newsy aspect of this: the narrative in itself will be a discovery.” At the end there I guess I’m trying to suggest that the fact that the history is new and untold itself counts as a news peg—convincing? Doug Most at the Globe and Veronica Chao at the magazine got this moving right along very quickly, and Francis Storrs, my editor on this story, supported staying inside the history and not superimposing modern connections. 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. Do you try to strike the right balance with details? Like, did your first draft mention that Lane & Read at No. 6 Market Square was one of the first hardware stores, outfitting farmers and sea captains yadda yadda, and then take it out because—The Story! I didn’t go into detail about Lane and Read, but I’m sure there were other places I included background that ended up being pared back or cut. I do remember researching the correct spelling of the Read of Lane and Read, since at the time spelling of names was very variable, even in directories, and I saw both Read and Reed. 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.”

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. How is this possible that the idea of detective work didn’t cross the Atlantic? London launched their detective department only a few years before this, and I suppose it didn’t boast any super visible success stories that would have made U.S. police departments jump to try it out. In an early draft, I also spoke about the presence of detectives and proto-detectives in literature, including Edgar Allan Poe’s detective stories, and I intended to have a sentence or two about the godfather of all detectives, Eugene Vidocq, a colorful French criminal turned police operative. 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.  How many sources did you draw on to bring all these scenic details together? This is my favorite scene. I’m glad, thank you! The Dazzle material came from five or six contemporary sources, including Dazzle’s own fascinating account after his capture.

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. Was fact-checking this a bear, or no, because you had all your sources from years of researching your novels, all of which take place in the 1800s, and always include Boston among the novels’ settings?   It helps I already had some secondary sources handy, in this case, for example, a 1967 book on Boston police history called “Policing the City” by Roger Lane, and I had a good idea where to look for what I needed because of my past research. But few details would overlap closely enough to provide many short cuts. As I get far enough along in a draft of an article, I start an annotated version with footnoted sources for fact-checking; I have 136 footnotes for my annotated version of this piece. Fact checkers tell me that I make things easy for them, and for better or worse there aren’t any living people to track down for verifying quotes!

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. Did an earlier draft explain HOW Dazzle escaped? Are elements of your nonfiction stories always clamoring with each other for who/what gets told and what doesn’t? I can’t figure out exactly how he escaped! I think the other officers who seemed to be present, Asa Butnam and Charles Philbrick, would have watched the exits, since it’s clear from a Boston Post article of July 26, 1849, Clapp and probably Starkweather leave the hotel at some point (“when the gentleman [Dr Bigelow] arrived, which was after the officers had left”), and after weeks of chasing Dazzle, common sense would dictate to leave some guards. My guess is whoever guarded the exits or the hall outside the room didn’t do a great job, or maybe Dazzle slipped out a window from the room. Or could this have been another instance, like the one mentioned later about breaking down a door, of the (non-detective) police disobeying the orders of the still-unpopular and unproven detectives? I couldn’t unearth enough of the choreography to conjecture. There are so many holes in what we can know in material like this, which have never been gathered together before, so part of my job was to try to tell the story in a way that you usually don’t notice or at least don’t focus on whatever’s missing.

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. Was this the first evidence of “crowd sourcing” to solve a caper via newspaper? I didn’t get the impression it was unusual for police to use the newspapers in this way, but I haven’t specifically looked into the history of the practice.

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. Is this graph a way of fulfilling an editor’s mandate to address why now? The opposite! This was a real change of pace for me: I tried to curate the context for this piece more than my editor did. This sentence above is actually all that remained from what was originally a longer bird’s-eye-view, a paragraph similar to the one I quoted earlier from my pitch invoking modern techniques of investigation—Francis suggested cutting so we didn’t get pulled out of the moment. He was right. I also originally planned to be explicit about the fact that these first detectives have never been written about — thinking a reader would be interested in knowing that, but Francis also thought that wasn’t necessary. Here’s a meta-pontification from the earliest draft I have saved; it went right around this spot in the piece: “…it is strange to consider that the next sentence has never been written: The names of the first detectives to be appointed in the country were Charles Starkweather and Alexander Hopkins. Despite the historic significance for Boston and America, their names have been forgotten and the origin story of such a familiar public figure [i.e., the detective] in our lives left untold.” On the same point, check this out: I snapped that pic at the Boston City Archives. It’s an 1846 list of police officers, never published before, that includes the country’s first two detectives the same year they started their pioneering work, Alexander Hopkins and Charles Starkweather. Incidentally, don’t you love the guy’s name listed below Starkie’s, Henry “Harry” Henry?

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.” How many disparate sources did you rely on to braid all these details and fragments into a fluent narrative? Honestly, hard to say how many sources over seven or eight years (on and off, obviously) of gathering research. As one way to measure, the document into which I transcribed research is 129 pages single-spaced, 10-point font, which doesn’t include the additional research I downloaded or scanned. The official Boston police archive doesn’t go back to the 1840s. One of the early police chiefs, Edward Savage, did an important history with lots of the nuts and bolts about the department in these years. Savage’s raw material for that project is at Boston College, and the Boston City Archives has some police material (like the list of names) from this era buried in its collections. This piece could never have been written without Savage’s material and especially the contemporary newspapers. That’s what opened up the world and work of the detectives.

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. You have a law degree from Yale — has prolonged exposure to the structure of legal arguments influenced how you arrange/present a narrative? I’m not sure what stemmed from learning legal arguments and what came from resisting some of what I learned in law school, but for what it’s worth, I really didn’t start any creative writing until I found myself in law school.

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.  Not once do you mention the name “Bulger.” Is that disciplined devotion to this narrative or discretion?   Francis’ discipline! Whitey Bulger was on my list of contemporary references to invoke as early as the pitch, the ones excised from the piece under Francis’ guidance. I guess the ultimate question is when and where contemporary references are resonant rather than jarring in historical pieces, and the answer is probably subjective. “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. At first, Derastus is the protagonist. Later it seems like Dazzle is. But really, it’s the detective agency…how did you decide to animate this story? And can you walk us through some decisions you made to arrive at this place where a “new force” arises, one that will have significant implications, famous implications down the road? This definitely had to be an ensemble cast. I couldn’t gather enough on any single detective to isolate a true protagonist, though if I could have chosen any of them I think I would pick Hopkins, with his past as a convicted criminal and (maybe?) his detective work as an attempt at redemption. Clapp cultivated his public persona, which left me more to work with than the other detectives. Clapp and Tukey also hated each other, an ongoing rivalry I originally built into the piece but sacrificed for space. Since the lede starts in the middle of the overall story, my plan was to back peddle and briefly cover the state of the Boston police and the Tirrell acquittal as the motivation for forming the detective department, and then get to the characters of the detectives as quickly as possible. In my early drafts, spread over the next two grafs, I included some amusing low points for the detectives on their first cases. We cut them for space, but I kind of miss them: “The new operatives contended with small game and plenty of indignities. One Saturday evening, two shoplifters, pockets bursting with gloves and boots, knocked Detective Starkweather down hard, and to add insult to physical injury one of the shoplifters gave his name as Titus A. Peep, a New England colloquialism for being drunk… By that fall… Starkie, who had spent years running into burning buildings, crawled on his hands and knees [with Detective Eaton] at the corner of Court and Cornhill streets to look for a silver spoon and fork stolen from one of the newspaper offices.” You could sense in their early coverage the Boston papers snickering at the new detectives — kind of like in the beginning of the second act of every superhero origin movie, where the first time in costume the hero bumbles and the Daily Bugle runs a mocking headline.

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. What is this pamphlet? Was this the breadcrumb that launched this story, or was it a document you discovered once you committed to building the story, (or…)? A Narrative of the Life and Adventures of Francis Tukey, Esq., City Marshal of Boston by One Who Knows Him–! It was published by the Boston Herald, the editors of which despised Tukey, so it was one of many documents I used that required balancing valuable information with an obvious bias. I believe I first glanced at the pamphlet—maybe more accurate to call it a booklet—in the BC archives in the Edward Savage collection, but only scrutinized it years later when I fleshed out Tukey’s place in the story. The accusations against Tukey in it are just wild, making him out to be a homicidal monster.

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. Sheesh, those were the days. And what follows boggles the mind. I have to eulogize here the enormous amount of time and energy I wasted figuring out if the victim’s name was Esters or Estes. You’ll see even in the fifth line of this 1848 letter from the City Council (from the Boston City Archives) the end of Esters’ name is scribbled as though intentionally trying to torment me: I’m pretty sure it was Esters, but in retrospect chasing that letter “r” all around Boston was a poor use of time. My thinking was this: There are two monuments to fallen police, one in Boston and one in Washington, D.C., that include his name as “Estes,” and by proving to myself it was definitely Esters, I could make a point in the piece about how without detective work on the case in 1848 the murder not only remains unsolved, even his memorialized name isn’t correct. But my editor didn’t seem particularly interested in this point, and when I think about it now it seems obviously a tangent. 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. Aha: intention opposed by obstacle — the meat and potatoes of plot. So do you find that there’s an interrelationship between your two jobs/genres — fiction writing and journalism. Do you see your work as bearing resemblance to police who consort with criminal informants? Seemingly at odds, but in the best-case scenario mutually beneficial? I hope the nonfiction writing sharpens my fiction writing, and vice versa, especially since most of my fiction is historical, research-based writing, as well. I guess I don’t spend too much time analyzing the different skill sets and creative spaces. I’d think it’s like if you played football one day, and the next day you play soccer. There’s overlapping skills but you know you’re playing a different game, and don’t have to think too much about the differences in order to switch back and forth. It’s muscle memory. (Disclaimer: I don’t play football or soccer.)

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. Seriously? Right? He didn’t have a college degree. Law school back then was very different than today, of course, and I tried and failed to get to the bottom of how unusual or not it would have been for a man with Tukey’s profile to go to HLS. In my first draft I hung a lantern on this point with this later-omitted sentence: “Exactly how he secured a spot at Harvard Law School and how he convinced Mayor Quincy to pick him as marshal has been clouded by time.” I also included and later cut this amusingly snide comment about Tukey becoming marshal made by a newspaper columnist at the time: “Nobody ever seemed to have heard of him until he was appointed.” 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. A criminal who fights crime; surely you know of present-day correlatives—is it hard to stop short of drawing lines to modern embodiments of this? I’d rather the reader draw those connections themselves. But I was frustrated not to be able to get much deeper under Hopkins’ skin, one of the reasons material like this lends itself so much better to a piece of this length rather than a book.

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.”

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. Picking back up on the initial story, did this article have other structures before arriving at this one? Once I knew I was going to stick to Dazzle and Bristol Bill as the main cases, the structure came together and remained stable. Narrowing the cases down to those two was the hard part. Originally, I searched for a single case that could run through the whole piece, a search that ended in frustration. Over time, the detectives received reports from their new “stool-pigeon” You don’t mention how the pigeons are rewarded…deliberate? True. The records are sketchy, so I wouldn’t want to be too conclusive about it, though later on Bristol Bill and Margaret O’Connor get deals in their own cases for helping go after Drury, so that’s one form of reciprocity. 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. !!! Filed under “You can’t make this stuff up” right…?? Honestly, I had no idea they would have even performed that kind of surgery back then. Showing how nimble my mind is, it took me a ridiculously long time staring at my notes before realizing this was the same doctor who came to Dazzle’s hotel when he escaped.

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. Details like this one and Dazzle observing the surgery? From whence do ye oulde specificities come? A 19th century police report? The police reports don’t survive, or if they do nobody whom I spoke with knows where they ended up. But the newspapers gave me fantastic material with which to work. Even compared to 10 or 15 years before this is set, the 1830s instead of the 1840s, which I’ve explored for another project (“Company Eight” in the Atavist Magazine), the newspapers had grown less formal and more inclined toward storytelling. The example of Dazzle asking for a Bible is from a defunct paper called the Boston Daily Bee. I know the Sacramento Bee is still around, but in general I feel like naming a newspaper the Bee basically guaranteed it wouldn’t survive into the 20th century.

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. As someone who writes historical fiction, did you have to squelch your impulse to add in imaginary details? Like, didn’t you want to dress up Dazzle in a cravat and say that his pocket watch got smashed on a cobblestone in the scuffle? Since the Globe commissioned illustrations for this, the artist got to do that kind of thing! It’s actually such a nice break for me from when I’m writing historical fiction and have to think about filling out every small detail. 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. Do you suspect Ben Affleck will play Dazzle? How does it feel knowing that all your hours of mining for meaning in the lonely archives will become a big-screen movie! That’s above my pay grade, but great idea! I know Chris Bremner, the terrific screenwriter working on it, plans to weave Dazzle through the whole story. I’m honored and, of course, excited they’d want to see what they can do with this.

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. Are you restraining yourself? As a novelist you have wide-open pages in which to flesh out characters; here, you have to “get on with it.” Are there arguments that you have with yourself when writing not just in a different genre, but in (relatively) shorter form? Like probably every writer ever, I tend to push for more space with the longform nonfiction I’ve done. This piece is the shortest of the ones I’ve published so far—around 4,600 words. But the bigger frustration here fell more on the side of things I wished I found find about my characters through research but couldn’t.

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. A novel in a sentence. 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. Another novel? This was on the opposite end of the spectrum to my detectives, in that I ended up finding tons of great material on Bristol Bill and his history, but didn’t have room to put them in without making the piece lopsided! 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. When you come home from a day of research, having uncovered THIS, does writing fiction feel—insufficient? Did you burn to tell this story to a wider audience? Do you test-drive the factual stories you uncover in research on friends and family members? If you did this in fiction, you’d be accused of trying to be Dickensian! Readers are so suspicious of coincidences in fiction, even though they happen all the time in life, and they drop those suspicions for nonfiction because, well, what is there to object to? As I’ve started to write more nonfiction, it’s definitely impacted how much I notice these sometimes strange differences between how we read fiction versus nonfiction, a whole separate question from the differences between how we write them.

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.

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.”) This is my favorite line in the story, a criminal trying to break into jail! When did you realize this was a story about defying appearances and expectations as much as it’s about historical developments in fighting crime? So much of this piece only developed while writing it. Sometimes it makes me nervous to pitch a piece without drafting it first, and I didn’t draft this until after I placed it. I didn’t anticipate Bristol Bill would be more than a straightforward antagonist, or how much the criminals and the detectives would blend and blur together, which I was very happy about.

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. So…a team of all-but-convicted-felon-detectives enlist a criminal to entrap an officer of the law gone outlaw? Yet if you put this scenario in a novel we’d think you were being preposterously cute. Exactly! It’s such a tricky game with fiction to play with and against reader expectations, and I just haven’t found that need so much in nonfiction. It’s like a free pass — it happened! 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 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. Drilling holes makes modern-day wires and body cams seem like cheating; What’s your favorite part of this elaborate narrative and why have you disclosed it here in this article instead of braiding it into a novel? These details didn’t get added in until one of the late drafts. Just after finishing the 5,000-word first draft, I rambled to myself in my writing journal: “There are also some things not yet well represented there, that I want to be in there, namely more on the methods and the personal aspects of the detectives, and the neighborhoods/settings of different moments.” Later, I tried to work more of those in. I’ve pulled up an email from Francis after he read one of those later drafts, with this kind encouragement: “I love the investigatory details you added. Surveillance! Rubber shoes! Such amazing stuff!” 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.) All this overlap—Dickens shows up in two of your novels, one as a cameo and one as a main character; do you even get confused coming and going in your work a la the great ’90s Dunkins commercial: Time to make the donuts/I made the donuts…? Dickens was everywhere back then! In a very literal sense it was a small world, after all.

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. Files you have happy access to? That would have been great! Unfortunately there’s no sign of them. In this case, Tukey included mention of the secret files in one of his annual reports to the city government, which thankfully do survive, noting the “private record of crime… kept by the Detective Force… the details of which are divulged only by the imperative requirements of justice.” Looking at that quote again reminds me that one of the things I noted in my writing journal was how I ended up using fewer quotes than I thought I would in this piece. I think I added some in the later drafts.

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 C’mon?! “Misted?” Surely you are embellishing? There’s so little in the historical material about what feelings and emotions they experienced, you have to take what you can find! This was not my first crack at how to end the piece, by the way. I originally ended almost immediately after the Drury arrest and closed with that always exciting word… “dictionary.” The last graf of that early draft looked like this, leaning into the rise of detectives beyond Boston: “[In the Drury case] [t]hey had carefully deployed those aspects of their newfound trade that sparked anxiety in the public and the press—using criminal informants, making extralegal arrangements, conducting unauthorized surveillance, and keeping details of their work secret to the point that detection came to seem ‘some magic art, some superhuman power.’ These innovations would produce highs and lows in the decades to come and into our own time. In Boston, unprecedented interest in its detective work began a few days after the quiet triumph of the Samuel Drury sting, when a member of the Boston elite went missing and a Harvard Medical School professor became the prime suspect, a case drawing in all five detectives with the eyes of the world on them. Within a decade, New York, Philadelphia and Chicago formed their detective departments, a testament to a two-person squad started in Boston’s City Hall before the word ‘detective’ was in the dictionary.” This was another place Francis impacted the content of the piece. He was a very thoughtful editor and challenged me to find a more character-driven way to wrap up. I thought about it and said, you know what, I actually have some material about Dazzle coming back to town later, this time claiming to be a colonel. We both thought Dazzle’s return tied everything together. as he took his leave from those officers who had pursued him as the original police shadows.

 

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