In 2007, Alberto Morrero was charged with sexually assaulting a woman in Fair Haven, Connecticut. Three years later, after the crime had been squeezed through the pasta strainer of the U.S. justice system, Art DiAdamo, bail bondsman, turned the crime into a $17,000 profit for himself by signing Alberto a bail bond, allowing him to get out of jail until his trial, months or potentially even years away — provided that he pay Art his commission.

Art DiAdamo has never met Alberto, but he has seen his picture and read his file. The bond, like many others bearing the imprint of the Arthur DiAdamo and Steve Tracey Bail Bonds Agency, was signed on the second floor of the New Haven courthouse, in a clerk’s office whose walls are incongruously adorned with prints of tranquil fishing villages. Business was transacted rapidly and impersonally between a short, red man named Wayne Lewis, who works for Art; Alberto’s diabetic fiancée, who is on social security; and Alberto’s brother, who looks just like Alberto, down to identical prison tattoos on his left hand, but who, unlike his brother, the sexual assaulter, holds down a night job in a warehouse.

Art was not there when Wayne asked the brother and the fiancée about Alberto’s brief employment history, about his education, about the scar on his back and the tattoo on his leg. Art was not there as Wayne filled out the paperwork, holding his fist balled around the pen, concentrating on the letters and sticking out his tongue. Art was not there when Wayne counted the Morrero family’s down payment, snapping the bills as Alberto’s brother and fiancée watched, silently, while the money formed in little piles. Art did not hear Alberto’s brother say, “You’re taking a chance on us. I want you to know we’re never gonna let you down.” Art did not see Alberto when he was finally brought up to the office by four bailiffs, when he play-punched his brother in the stomach with handcuffed hands, when he made a face at the bailiffs that was all eyes and twisted mouth, and when he bent down rapidly, still in handcuffs, to kiss his fiancée. Art was not there when the two Morrero men and the soon-to-be Morrero woman all walked out of the office, out of the courthouse, $8000 lighter and having pledged to wire DiAdamo and Tracey $100 per week, until the bond was paid in full — a process that will, according to Wayne, take “pretty much the rest of their lives.”

Instead, Art was on the shore of the New Haven harbor, at home in Morris Cove after a busy morning spent sitting on a bench of the lobby of the New Haven courthouse. He was getting ready to settle down into some paperwork, sipping coffee and finishing a nice lunch with Lorraine, his wife of forty-five years.


Before going home, where lunch and Lorraine usually await, Art spends his mornings within the edges of a small triangle of city blocks whose three points are formed by a darkly lit luncheonette called Alpine, where Art’s nephew and business partner, Steve Tracey, eats breakfast every morning; a Wachovia Bank, where Art cashes checks and verifies that his accounts are in order; and the Superior Court of New Haven on Elm Street. Art has spent each morning for the past several decades within these borders, even though he deals with plaintiffs and criminals, defendants and families, the guilty and the accused, from all over southern Connecticut.

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Small and brown and bald, with a deeply cut face and wild eyebrows, Art is almost a foot shorter than Steve, a fat and quiet man who has heavy lips and hooded eyes and slicked back hair that appears to be frozen still in time. Steve’s heft, which clocks in at just over 300 pounds on a good day, has earned him the moniker “Big Steve,” but occasionally, the rare few who remember Steve’s days in the WWF will call him by his half-forgotten wrestling name, “Dave Paradise.” When uncle and nephew walk to or from Steve’s black Hummer in the parking lot across the street from Alpine, Art buries his nose in his red scarf and looks down at his hasty, creaking feet to see where he is going. Steve towers by his side, waddling like a duck from his massive weight. His gold watch and chain knock slowly against his big wrists as he explains a thought or two to his uncle, who absorbs and weighs.

The lobby of the New Haven courthouse — but never the clerk’s office, one floor above — is where Art DiAdamo comes to work every day. His office, as he calls it, is a bustling but well-functioning place where people congregate in corners, where the lawyers explain, where the public defender rushes, where the cousins of the accused wait, where small children slide shrieking across the polished floor, and where Art, sitting on his bench, measures the scene.


When someone is arrested and charged with a crime, a judge sets bail as an incentive for the accused to appear for court sentencing. Although bail money is ultimately returned to defendants, most of the accused can’t afford to post bail — which can run from $10,000 for less serious forms of domestic abuse, to $200,000 for crimes involving weapons, to millions of dollars for homicides — but would rather not spend in jail the uncertain weeks or years it takes for a conviction to mature into sentencing. This is why the accused turn to a bail bondsman, who, in exchange for a nonrefundable percentage of the total bail (usually 10%), will write a bond that guarantees to courts that the accused will show up for sentencing. If the accused neglect their duty and no response is heard in the heavy-breathing courtroom when the defendant is called forward, the bondsman must pay the court full bail. At this ruinous yet quite electric moment, which requires the bondsman to pay 10 times as much as he received for writing the bond, he is given full legal license, and a fuming personal prerogative, to hunt down his debtor.

Though bail bonds are signed and reneged on every day throughout the U.S., they are illegal in the rest of the world, save for the Philippines. The two countries use the system because it saves their governments the hassle and cost of having to track down no-shows themselves. But expediency does not always serve the oblique interests of justice, and within the U.S., the states of Illinois, Oregon, Wisconsin, and Kentucky have made bail bonds illegal, claiming that bail bonds discriminate against poorer defendants and usurp a responsibility that should be carried out by the justice system rather than by businessmen.

Bail bonds originated in the U.S., as a legal innovation in the late 1800s, when private businesses and commercially-minded individuals were first allowed to post bail in exchange for payments from defendants and the concurrent promise to hunt them down if they never made it to court. The legalization of bail bonds codified a practice that was already widespread across the American frontier, but the hunting of citizens by strangers unaffiliated with the law is a custom almost universally viewed as a devious ethical practice and actually loathed by most bondsmen today, who prefer business to the chase, prefer money to risk, and will draw from their deep toolbox of resources — menace, intimidation, cajolery, property seizures, phone calls in the middle of the night to the mothers or sisters of those on the lam — to avoid having to run a client-turned-debtor down a stinking hallway, across an icy backyard, through a jagged street at night.

For every bad bond written, it takes 10 or 20 to recover the loss incurred. Steve and Art have 5 million dollars out in bonds at any given moment. If their debtors suddenly vanished, uncle and nephew would owe courts around Connecticut close to half a billion dollars. “We’re gamblers,” Steve says of the family business, of the prolific disgorging of freedom in the form of paper squares. “We take a chance each time, on every bond we write. It’s like rolling the dice on whether they’ll make it to court.”


Bondsmen are commanders of paperwork battles (Wayne, with accompanying fist-thrusting motion: “If you don’t keep track of the docket number on every sheet in that packet, you’re prffffflrpp”), turbo-charged secretaries (Freddie: “Where’s that number, Wayne? I got you four pieces of photo ID and you still got no number?”), veterans of phone call strategies (Steve: “Call every five minutes until she fucking picks up!”), unsleeping maniacs of order and industry (Wayne: “I always sleep by the phone. Like it says, when it rings, I spring!”), heavy-handed thugs (Steve: “You break the camera in the entrance of the building and you wait for him to come out and then you get him good!”), and arbiters of good and evil (Art: “You know, it wasn’t really rape, what he did”). They spend most of their time filling out reams of paperwork, troves of paperwork, pocketfuls of paperwork.

But Art does little paperwork these days. A few months ago, he got an iPad, which has since become his navigator’s compass. He uses it to check case information from his bench, to write down bond amounts and dates of birth, to keep track of his millions of tiny streams of payments. And at times, he uses the device the way most people would: to check email and to watch videos, which he does by flicking the screen with a loose finger that swishes, free, unrushed by the urgency of his job.

This is the rich privilege of Art’s old age. Art no longer personally writes bonds. He lets Steve and Wayne and a bondsman named Freddie do the ink work and signing. Art no longer bounty hunts either, and has not done so in a decade. Instead, his nephew takes calls concerning the day’s pickups, while he eats breakfast in the semi-dark of Alpine’s grey basement light.

One morning, Wayne calls: he has picked up a skip in East Haven, an illegal Mexican immigrant charged with drug dealing who had forgotten to go to court. Wayne found him in his backyard, and, though he carries a gun whenever he makes a pickup, there was no need to use it. Wayne just shouted a little, and the Mexican’s eyes got big, and he stood still. Wayne has never used the gun and hopes to God almighty he never will. For his pickup in East Haven, Wayne will get 10% of the bond, and Art and Steve will split the remaining 90%. In the courthouse that morning, Wayne will go see Steve to collect, and Steve will send Wayne over to Art, and Art will send Wayne back over to Steve. The two bosses have done this to Wayne many times before. They haggle, even when there is no need, for the joy of business.

“Give the kid his check!” says Art. Wayne, with long, red eyelashes, blushes.

“I told him you would give him the check!” Steve replies.

“C’mon!” says Art, but Steve doesn’t budge. His mouth curling into a thin smile, Art writes Wayne his check.


The first bail bondsman was an Irish-American named Pete McDonough. He wrote the first bond in San Francisco in 1898. By the time McDonough died, he was one of the richest men in the city and had been accused of numerous crimes: bribery, perjury, bootlegging, corrupting officials, and paying off the police.

Given how well the bondsman knows the failings of the legal system from having spent his working life cataloguing them alongside the milestones of his own career, he cannot help being the victim of a recurring tendency to oil the corroded ducts of the malfunctioning legal machine. Art’s position as the reigning bondsman of the Elm Street courthouse is the recent outcome of another bondsman’s surrender to exactly such temptations. In 2007, a bondsman named Bobby Jacobs, whose face is fleshier than Art’s but of the same knotty mold, was brought down, along with his three sons and hundred-man bail bonds operation, on charges of corruption. When Jacobs was caught by the FBI for paying on-duty New Haven policemen to pick up skippers for him, the 81-year-old man pleaded with the judge to spare his two sons.

The bail bonds industry favors clan-like formations. Loyalty and trust are paramount, given the amounts of cash and discretion constantly entrusted to each bondsman in the business. The defense tried to turn the bondsman’s paternal instincts toward his sons and business to his advantage by pleading for the judge to punish with leniency because the old man had already been burdened with the guilt of having misguided his two sons. But in the end, Bobby Jacobs and his boys were sentenced to a $750,000 forfeiture and a jail sentence of three years.

Since 2007, the DiAdamo firm has replaced the Jacobs agency as the dominant family of the New Haven bail bonds industry. Although the current bondsman king of the New Haven Superior Court views bail bonds as a decent trade that provides little incentive to cheat or deceive, Art is wary of Jacobs’ fall from grace. He takes precautions, which his demeanor records: his continually raised bush of an eyebrow is the inadvertent relic of years of suspicion and cynicism.

Yet some of Art’s carefulness is quite deliberate.

Steve and Art call each other uncle and nephew and live around the corner from each other in Morris Cove, where they eat dinner at each other’s houses several times a week. The two men are business partners and best friends, and though few of the men who work for them doubt the authenticity of their bond of bickering love, Steve Tracey and Art DiAdamo, uncle and nephew, are not related by blood. Years ago, Art conferred on himself the avuncular title and stretched his informal but involved mentorship into a biological fact.

Art and Steve began to call each other family around the same time they went into the bail bonds business together, after dissolving their nascent towing business when one of the men who worked for them went on a beer bender and smashed a police car he had been tasked to repair into the foot of the East Rock cliffs. The closeness of Art’s ties to Steve has to do in part with Art’s fear of being crossed, of getting screwed. Steve, on the other hand, looks up to the diminutive Art as he would to a father. His own father beat him until he left home in the 9th grade to join the WWF. Until meeting Art, Steve had never had an older mentor to give him firm but respectful advice.

Family ties are imperative in a business that sees constant betrayal. Art and Steve have been crossed several times by cold-shouldered relations, but they themselves can be loathsome partners and have hung their own friends out to dry. 12 years ago, Freddie, Wayne, Steve, and Art all worked together, as partners, along with a fifth man named Fitch. The team lasted for five years. When Bobby Jacobs was arrested and a vacancy opened up at the top of the New Haven bondsman chain, Art and Steve split off to resume business as family. “Fitch was the greatest partner,” says Art. “A better partner than I.” But with Jacobs gone, there was an opportunity for action in the lobby of the New Haven courthouse, and Fitch, a very large man who in his prime weighed 700 pounds — twice as much as Big Steve — was getting sick.

After his second or third heart bypass, Fitch would whine to Freddie that his heart was giving and his stomach was collapsing. Like his body, Fitch’s business deteriorated. “If people don’t pay a bond,” says Art, “your life is done, people prey on you.” In those years, Wayne hated Big Steve because of a bond they both claim to have written, yet for which Steve alone reaped the profits. But Wayne could no longer make ends meet, and he left Fitch to join the competition. Fitch died shortly after, and Art expanded. “In this business, ya can’t ever get sick,” Art says as he massages his throat. “Ya can’t ever stop going to work.” Freddie also put aside his resentment toward Art, and reluctantly asked him for a job: “You make amends,” he says. “All bondsmen are the same. The business is the same everywhere. Gimme the money. That’s it. That’s all it’s about, all the work is about. Gimme the damn money.


No guilt of any sort can make Art forget that he is running a business. “It’s like cleaning a fish,” he says. “You know the joke, right? The guy goes, how do you do that? Well, you just clean the fish.” Art can’t stand those who criticize bail bonds without admitting that there is no alternative, that bail bonds and U.S. justice will grow old together: “People profit from it. I profit from it. But I didn’t create it! Yeah, it bothers me. Sure it bothers me. But is it my fault?”

On the surface, the bondsman, and his hard work, and his lidless hours, and the great gamble he undertakes with each new bond, all seem to have something of the Real Right American Thing: a dose of chance, a bit of roughing, but mostly a lot of toiling by the midnight phone. Yet Art’s profession takes him to the heart of life on the receiving end of inequality in America, without which the bail bond industry could not exist.

One Monday, Art is sitting next to the family of a 16-year-old African-American girl named Jamece Hudson, who was shot in the stomach and killed, the day before, by an 18-year-old friend. Hovering over his uncle, who watches sports news on his iPad, Big Steve examines the crime section of the New Haven Register. The woman sitting next to Art says something about the murder, and Steve lifts his head from his reading. The woman is the victim’s cousin. Art is engrossed in CNBC. Steve says:

“Art, you didn’t hear about this? The shooting accident with the 16-year-old girl?”

The woman sitting next to Art says to Steve, “No, it wasn’t no accident. It wasn’t no friend neither. The papers put that in there. That girl ran away after she shot my cousin.”

The woman tells Steve that she and her family all took a day off from work to come down to the courthouse. She bounces her little boy up and down her thigh.

Art glances over for a second and mutters, “They all took a day off from work, yeah right. What work … Friggin’ highlight of their day is what it is …” and returns to CNBC.


Within their country, Americans move around more than any other people on the planet. But the map of U.S. crime is fixed and suffocating. Criminals and their victims are frozen by their demographics. The overwhelming majority of rape victims are women. African Americans are 27% more likely to be victimized by violent crime than whites and over six times more likely to be murdered. The poor are more likely to be violently victimized than the rich, and the young more likely than the old. Poor blacks are more likely to be caught on both ends of violent crime than any other segment of the population. They are more likely as well to do drugs, to smoke too much, to beat their spouses, to get sold bad mortgage loans, and to buy bail bonds.

Art knows that the rules governing his courthouse are founded on these abstract determinants. He sits like the still eye of a hurricane amid victims who move helplessly through the storm, returning to him with each new generation. “I got a kid come up to me, maybe fourteen, fifteen,” says Art, “and he says, ‘Mr. Di, you remember me? You wrote a bond for me, my ma, and my grandma!’” Art once ran the idea by Steve of embossing business cards with Disney characters before handing them out to kids in the courthouse lobby, so they might know whom to call when they came of age.

There are rare days when Art lets himself feel compassion, and on those occasions he is choked by futility. But he always returns himself to healthy cynicism with a good shot of common sense: “The government is inefficient. It’s too big a country to be efficient. The police couldn’t catch everyone who skipped court. It would take forever and cost a whole lot of money. We’re actually saving everybody money. You know how much it costs to keep someone in jail?” asks the hardnosed bondsman, an incredulous note creeping into his voice.

Art reserves a spot in his rough old heart for battered girls, and admits to getting upset when he sees “a pretty little girl, strung out, whoring herself out.” However, Art has never felt compelled to show special treatment to a woman who works in the bonds industry out of concern for the intrinsic vulnerability of her gender.

When Bobby Jacobs’ daughters, who were not implicated in their father’s scandal, tried to revive the family business, Art pushed them out of his courthouse. The Jacobs daughters sometimes still pass through the Superior Court, but without much success. Art disdains the sisters for trying to unseat him, and for failing. “They’re just filthy,” Art says of the sisters. “They’re just disgusting.”

Nevertheless, says Art, “For me there’s still a girl-boy thing. I put girls on a pedestal.” Art’s wife falls under this doctrine. Lorraine, whom Art alternately describes as “the smartest person in the world” and as “a very well-kept woman,” is a tad younger than Art. He says, “People ask me sometimes if I’m her father.” The truth is that Art is 67, and his wife is 66. But Lorraine is a part of Art’s home life, and Art needs to keep home life separate from his life at work — mornings in the courthouse, and afternoons at home — though so much of his life consists of work. Art does not want the disgust he sometimes feels, as a bail bondsman, to infect those things that still deserve, after all these years, his tenderness and respect, such as Lorraine, whom he shamelessly adores.

When they were still in high school and first dating, Art would take Lorraine for damp-palmed walks through Wooster Square. Art especially enjoyed taking his beloved through the square when the trees began to turn, and the freshening air sharpened desire, and Art’s favorite local holiday rolled around, the Italian Feast on Wooster Square, because it was, Art says softly, “quite the place” in those days, with rows and rows of families and folding chairs, and mounds of food and drink spread out on checkered tablecloths.

But Italians no longer live in Wooster Square, and Art’s nearby childhood home, which once stood, solitaire, on the corner of Chestnut and Water Streets, has been razed, along with the whole block on which it stood, to make room for a column that supports the I-95 highway now bisecting the entire city.

Many of Art’s habits began in his childhood, and if he drives himself to Mass before going to work every morning, it is only because he started to do so when he was sixteen, at his mother’s request. In his spare time, Art likes to attend benefit dinners for local Catholic schools, one of which he attended, long ago. But Catholic schools, says Art, “are just like me: a dinosaur; in twenty years there’ll be nothing like ’em left.”

Houses are razed, married couples grow old, Catholic schools disappear, but money remains a human need. This is a fact around which Steve and Art construct their lives. Art will go on with business to his very last breath. The money from bail bonds is a gain achieved at the expense of the U.S. justice system, by raiding the pockets of the poor, but the job is hard work and the money it brings feels heavy and right. A year ago, Art and his wife sold their condo in St. Thomas. These days, in March, they prefer Aruba. “Art does very well,” says Steve; says Freddie; says Wayne.


When his office becomes overcrowded and Art sees other bondsmen tempting their fortunes in his lobby, he gets angry. As Freddie says, “Anybody else who comes here, they taking food away from you.” It is not by any means a steady or secure job; bail bonds are a volatile trade with quick turnarounds, dry seasons, and thousands of uncertainties. Some mornings, Art will come out of arraignments without many hopes for a bond, and Steve, Freddie, and Wayne will have turned up nothing from their morning hustle on the lobby floor. Freddie will blow a raspberry as he removes his Kangol cap. Steve will slowly rub his hands together. Wayne will sigh, “Nothin’.” Art will agree: “Slim pickins.” All four men will leave the courthouse, side by side, to buy half a dozen hotdogs from the man on the corner of Elm and Whitney and will walk back to their cars, munching. There are no hard feelings, though, because such is the nature of the job, the way of the world. There are no feelings at all, as a matter of fact: it’s just business.