CHAPTER ONE
Different Paths to the Same Courts
TIM AND I MET at a local grocer in Cambridge. After we found a table and sat down to begin the interview, I studied his face as he quietly filled out the survey I provided to everyone in the study before I started the tape recorder. He is black, in his early forties, and has a weary appearance. His wrinkled forehead and small chin combine to make him seem at once older and younger. Next to his chair that day, he had carefully placed a raggedy suitcase and an overflowing messenger bag. I would learn that these items were his only possessions. He carried his belongings everywhere he went because he did not feel comfortable leaving them at the shelter where he had been staying for the past several weeks. âI donât like staying with a whole bunch of people because thereâs a whole bunch of guys and everybody has a story to tell. Sometimes I donât want to be around that drama,â he reflected once we had started the interview. Nowadays, Tim tries to keep to himself. He has been arrested eight times in his life, and many of his arrests arose from âdramaâ he has had with other people on the streets.
Timâs life has been marked by multiple forms of disadvantage, all of which combined to make his involvement with the criminal legal system seem inevitable. He grew up in the 1980s in public housing in Roxbury, a majority-black neighborhood in Boston. In his childhood, his mother was an inconsistent presence; his aunt raised him, providing him a home in a cramped apartment shared with several cousins and with just enough food and clothing between them. Growing up in Roxbury in the eighties meant that he regularly witnessed drug dealing in both his neighborhood and at school. âEveryone sold dope,â he told me. The police were ever present; they seemed eager to harass the âkids in the projects.â âMan ⊠the police used to stop everybody,â Tim remembered. Police harassment followed them elsewhere, too. Timâs first time being stopped and searched was when he was shopping at Downtown Crossing, a bustling outdoor mall in the center of Boston, with a group of other young black boys, the summer of his thirteenth birthday. âWeâd just be chilling because we got a little money from our summer jobs, and [they] come and pat us down.â
In his teens, Tim and his friends started experimenting with marijuana and alcohol. After high school, and after moving out of his auntâs apartment, he moved to Atlanta, Georgia, looking for work and eager to start a new life. But within a few months, he began selling cocaine to make ends meet. He quickly found himself homeless and spending nights at the airport, where he and others sought shelter. Just after he turned nineteen, he was arrested and jailed for trespassing. When he got out, all his belongings were gone. With no family or friends to support him, he started selling drugs to survive. Sometime in the next several years, he was arrested for cocaine possession and spent eighteen months detained in jail awaiting trial. âIt was a big zoo,â he remembers of the county jail in Georgia. After serving time, he moved back to Boston, where he has spent about a decade revolving between the streets and jail. His life has been shaped by avoiding, and far too often enduring, punishment from various components of the criminal legal system.
When we think about the typical criminal defendant in the United Statesâwhether we are a researcher, a journalist, or an activistâwe often imagine someone like Tim. A childhood of poverty and instability, the descent from drug use to drug dealing, the persistent presence of the policeâall these features are terribly common among people involved in the criminal legal system. But portrayals of people like Tim do not tell the full story of our criminal legal systemâs reach. In fact, portrayals in scholarship and the media that focus exclusively on the disadvantaged often obscure just how unequal the criminal legal system really is. To fully comprehend the systemâs inequality, we must contrast the experiences of people like Tim with the experiences of the privileged.
Ryan is a white man in his early thirties who grew up in a middle-class family just outside Boston. He has walked the path into the court system typically taken by privileged people. The two of us met at a food court in Boston on a warm summer morning. He was wearing khaki shorts and an untucked polo shirt. He shook my hand graciously before we sat down. Unlike Tim, but like a third of the people I interviewed, Ryan was raised in a well-to-do two-parent household.1 His parents are both college educated. To this day, his mother works as a paralegal, and his father works as a health insurance agent. No one in Ryanâs family ever expected he would be arrested. But so far, he has been arrested three times in his lifeâtwice for driving under the influence and once for shopliftingâcrimes that stem from his addiction to alcohol and other drugs.
Despite his middle-class upbringing, Ryan has struggled with addiction since adolescence. His middle school and high school were both resource rich, the kind of quality suburban public education that many poor parents dream about for their kids. Ryan was an average student, did not find academics enjoyable, and did not establish meaningful relationships with his teachers. But he loved sports. He played on the soccer and golf teams in the fall and the basketball team in the winter. High school also brought peer pressure and the excitement of experimenting with drugs. In his teens, he started drinking, smoking marijuana, and using benzodiazepines (a class of antianxiety drugs). His parents did not know about the drug use, but they were well aware of his underage drinking. Even though his parents both struggled with their own alcoholism, as Ryan explained, âthey werenât aware that it could be genetic or anything.â They thought his drinking was just harmless teenage fun. And neither Ryanâs parents nor his friends were concerned about getting in trouble with the law. One time, he and some friends were pulled over by a police officer with âfour open beersâ in the car but âgot by on the skin of our teethâ; the officer was an acquaintance of one of his friendsâ parents, and he let them off with a warning.
It was not until college that Ryanâs drinking created bigger problems. In the dorms, drinking became routine. âIt was Thursday, Friday, Saturday, Sunday during the day,â Ryan remembered. One weekend he was driving drunk near campus. An officer pulled him over. âI was scared shitless,â Ryan told me. The officer was courteous but still arrested him. He spent the night in jail, got bailed out by his girlfriend the next day, and was charged with OUI in court that Monday. Terrified and confused, he called his father. âI wasnât brought up that way, and Iâd never seen myself in that situation.â Ryanâs father contacted a friend who was a detective. The detective put him in touch with a reputable lawyer, who just happened to be the son of the countyâs DA. The lawyer negotiated a standard plea deal but with light termsâa CWOF with six months of administrative probation, meaning no conditions were attached to his probation time. After making it six months without another arrest, his probation would be over and the whole court experience behind him. He graduated college and got a job in investment consulting. Because his charge resulted in a CWOF, he was able to apply for jobs without reporting the OUI.2
For a while, he lived a typical middle-class life. But in his mid-twenties, his alcoholism got worse. His addiction was abetted by the âwining and diningâ of corporate culture. And then he started drinking alone: âI wasnât out at bars. I wasnât hanging out with friends. I was by myself, isolated.â He was arrested on another OUI charge. Later, he would be hospitalized and induced into a coma for problems with his pancreas. His girlfriend left him. He lost touch with most of his friends from high school and college. He moved back in with his parents and worked toward recovery, including stints in a revolving door of residential addiction programs, financed by his parents. âMy parents have helped me out with anything I needed in between,â he said. When we first met that summer morning, Ryan was living in a halfway house in Jamaica Plain, a racially diverse and mixed-income neighborhood in Boston, and dealing with a shoplifting case. He had recently been arrested after attempting to steal a vaporizer from a store while high. This was his third arrest. He was nervous about the court case. But he was almost certain he would get off with a light punishmentâa small fine, he guessed, or perhaps another CWOF with six months of administrative probation. His past experiences with the law suggested he had little to worry about. Later in the book, we will see he was right not to worry about this most recent case.
At first blush, it may seem odd to focus our attention on a privileged person in the criminal legal system. We tend to imagine our countryâs jails and courthouses to be filled almost exclusively with poor people, especially those of color. To be sure, people with middle-class resources who live in predominantly white communities are substantially less likely to become defendants, even if they struggle with the same problems (and resort to the same crimes) as the poor. Problems such as social alienation, depression, and drug use, as we will see in this chapter, are simply treated differently in privileged communities than they are in poor communities. But then, even when privileged people do happen to be arrested, their legal involvement looks differentâand even means something differentâfrom that of disadvantaged people, given their privilege in broader society. Thus, the âprivileged defendantâ is something of an oxymoron, an intentional one that is meant to illuminate how the privileges some people benefit from in everyday life can soften their experiences with the criminal legal system in numerous ways.
As Ryanâs story reveals, being both privileged and a criminal defendant means that certain criminalized behaviorsâsuch as underage drinking and drug useâare often constructed as pleasurable diversions. When caught, the police often give privileged suspects the benefit of the doubt or grant second chances until they can no longer justify them. Arrest, or other forms of legal involvement, are an unexpected shock in the world of the privileged. Timâs story reveals the near opposite. Being both disadvantaged and a criminal defendant means that crime often feels like a necessary, even an inevitable part of life, given the fundamental constraints of poverty and racial marginalization. Arrest and other forms of legal surveillance are routine. When stopped by police, the police rarely accept explanations and often represent a threat to oneâs freedom and physical safety; police who are supposed to protect and serve are instead a palpable reminder of racism and classism. Ultimately, these negative experiences with the legal system and police sow seeds of distrust among the disadvantaged.
This chapter examines how people from different walks of life end up in the same situation: being a criminal defendant. I argue that privileged people walk a strikingly different path to court than disadvantaged people, even when they engage in similar behaviors. These different paths, and the different ways their behaviors are treated by police and other legal officials, contribute to divergent perceptions of the criminal legal system and, eventually, of their defense attorneys. Becoming a privileged criminal defendant carries very different meanings, and involves a very different set of experiences, than becoming a disadvantaged defendant. These divergent meanings and experiences ultimately color the attorney-client relationship. While the meanings they attach to crime and their experiences with lawyers diverge greatly, one thing is common across race and class lines: the sense of alienationâwhether from family, teachers, and peers or from neighbors, the law, and broader American societyâthat appears to sustain and justify the problems and harms that draw the attention of legal officials.
Alienation in Adolescence
No matter their background, nearly all the defendants I met described an adolescence marked by social alienation. Scholars have long defined alienationâand related concepts such as anomieâin various ways.3 I define social alienation as a personal feeling of separation or rupture from the expectations and norms of institutions and broader society. A person can feel separate from the expectations of their family or school (two institutions) or from societyâs seeming valorization of attending college or purchasing a new home (two dominant norms). This separation can emerge from distaste for such expectations and norms or from strainâthe feeling that one cannot meet societyâs expectations about how to be a well-behaved child, a smart student, or, as one grows older, a productive employee.4 Structural differences in the quality of peopleâs schools, neighborhoods, and experiences of discrimination in the labor market contribute to strain, often to the detriment of poor people of color.5 Moreover, alienation can exist in relation to the law as an institution. Cynicism about the effectiveness of the law in marginalized communities can make it difficult to rely on the police in moments of trouble.6 Rather than rely on police or other legal tools provided by the state, gang involvement and other criminalized activities may better ensure oneâs safety. Such legal cynicism does not exist to nearly the same extent in privileged communities, given differing structural realities of policing.7 But privileged people in this study do experience strain and separation from other institutions, often emerging from or manifesting as abuse in the home, parentsâ and teachersâ inattention, and unmanaged mental illnesses.
Feelings of alienation alongside structural constraints contribute to the problems and harms commonly faced by the people in this study. These problems and harms are criminalized by the law, explaining eventual arrest. Some in the study felt alienated at home, where they feared abusive family members or were ignored by inattentive parents. Others felt alienated at school, where their learning difficulties meant teachers excluded them, or where their boredom was supplanted by the diversions of peers doing reckless things. Still others experienced alienation from peers, neighbors, and the expectations society suggested for their futures. Given these feelings, people reported engaging in illicit activity of one kind or another, often to cope. Just about everyone had committed a crime by the time they were eighteen, with drug use, drug dealing, and larceny the most common. Many struggle with substance use disorders still today. Eighty-five percent of the defendants I interviewed reported current struggles with substance abuse, commonly alcoholism and opioid addiction.8 Nearly as common are struggles with mental health. More than 60 percent of the people in the study responded âyesâ to at least one survey question indicating possible depression at the time of the interview.9 Other mental health conditions described in interviews include attention-deficit hyperactivity disorder, bipolar disorder, and schizophrenia.
When it comes to sources of alienation, physical and verbal abuse from parents and guardians was commonly mentioned no matter their race or class. Christopher, a heavy-set white man in his late thirties, spent most of his adolescence with his aunt and uncle in South Boston, a majority-white and largely working-class neighborhood. His aunt, a college-educated nurse, and his uncle, who worked in the piping trades, provided him a nurturing middle-class home and paid his tuition for Catholic school. Before moving in with his aunt and uncle, Christopher had spent the first twelve years of his life with his bi...