Readers of Freakonomics have met this author before: Sudhir Venkatesh was the source of that book’s fascinating explanation of why so many drug dealers live with their moms. A graduate student in sociology at the University of Chicago during America’s crack epidemic, Venkatesh spent years around members of the city’s Black Kings gang. He even got a copy of the gang’s ledgers, which showed that, while a few top leaders of the organization were paid handsomely, the majority of drug sellers–the guys on the street, those most at risk of arrest and injury–earned very little. The compensation scale, in other words, was very much like that of many major American corporations. The dealers lived with their moms because they had to.

Following the success of Freakonomics, somebody realized that Venkatesh–now a tenured professor at Columbia University–probably had a pretty interesting story to tell about his gang days too, one that might attract a larger audience than his two books of sociology, Off the Books and American Project. And so we have the strangely titled Gang Leader for a Day.

It gets off to a brilliant start. Venkatesh, a ponytailed math major from suburban San Diego and the son of immigrants from India (his father is a professor too), wanders from cosseted Hyde Park into one of the poor neighborhoods that surround the university on Chicago’s South Side. His professor, William Julius Wilson, is mounting a new study of urban poverty, and Venkatesh has volunteered to help administer a questionnaire. He’s looking for young black men, and Census data in the university library point him toward a building in the Lake Park housing projects in nearby Oakland.

Told to get lost by gang members who are selling drugs in the lobby of the first building he enters, he moves on to a second. This lobby is deserted; seeking subjects to interview, Venkatesh climbs up a smelly staircase to the fourth or fifth floor, clipboard in hand. There he finds a group of his intended demographic shooting dice. Suspecting he’s been sent by a rival gang of Mexicans, they circle around, one brandishing a knife; as Venkatesh tells it, he goes ahead with his administrative task and asks the first question on the survey: “How does it feel to be black and poor?” The multiple-choice answers are “very bad, somewhat bad, neither bad nor good, somewhat good, very good.”

“Fuck you!” says one man. “You got to be fucking kidding me.”

The question is, indeed, so ludicrous that the reader not only applauds the gang member but may be forgiven for wondering if the celebrated Professor Wilson really sent his graduate student out on such a risible mission, or even whether–forgive me–this little part of the tale, which took place back in 1989, is apocryphal.

But no matter. The more important thing is that Venkatesh, told not to leave, is eventually confronted by the gang’s leader, J.T., with whom he establishes a relationship that lasts for years. J.T., with “a few glittery gold teeth, a sizable diamond earring, and deep, hollow eyes that fixed on mine without giving away anything,” quickly takes charge of the situation:

He took the questionnaire from my hand, barely glanced at it, then handed it back. Everything he did, every move he made, was deliberate and forceful.  I read him the same question that I had read the others. He didn’t laugh, but he smiled. How does it feel to be black and poor?  ”I’m not black,” he answered, looking around at the others knowingly.  ”Well, then, how does it feel to be African American and poor?” I tried to sound apologetic, worried that I had offended him.  ”I’m not African-American either. I’m a nigger…. Niggers are the ones who live in this building. African Americans live in the suburbs. African Americans wear ties to work. Niggers can’t find no work.

Certainly intending no disrespect to his academic adviser, Venkatesh writes that the gang leader “was about to become the most formidable person in my life, for a long time to come…. I felt a strange kind of intimacy with J.T., unlike the bond I’d felt even with good friends. It would have been hard to explain then and is just as hard now, but we had somehow connected in an instant, and deeply.” J.T., after a getting-to-know-you period, accepts Venkatesh as his Boswell, taking him under his wing, offering him access and protection. Eight months later, when J.T. moves his business out of the Lake Park projects, which are slated for demolition, and heads north to the massive Robert Taylor Homes, Venkatesh follows. (HOPE VI, the federal public housing renewal project, eventually leveled and replaced the Robert Taylor Homes, as well, with lower-density housing.)

In terms of journalism, the gold standard for writing about life in the projects was set by Alex Kotlowitz with There Are No Children Here (1991). It also takes place in Chicago, just before Venkatesh’s research began. Though he makes no mention of that book, Venkatesh borrows from the techniques of Kotlowitz and other literary journalists, focusing on a set of main characters, setting scenes, using lots of dialogue and–much more than Kotlowitz–putting himself into the story as narrator.

But his story is different. Where Kotlowitz sharply evokes all the fear and randomness of the projects, aiming to spark reader empathy with his main characters, Pharoah and Lafeyette Rivers, ages 7 and 10, Venkatesh is more interested in understanding and explaining the big picture. Gangs are violent and too powerful, yes–but why is that? How are the police involved or not involved? What are the economic relationships between people in the projects? Venkatesh has ceded the family-level focus to Kotlowitz; there are very few children here.

But what is here is truly remarkable. As he grows closer to J.T. and then, feeling suffocated, experiments with moving outside J.T.’s sphere of influence, Venkatesh is present for just about all the kinds of things one fears could happen in the projects, and then some. For starters, he witnesses at least two drive-by shootings: after the first, he says, he was the only one left standing (because everyone else was smart enough to hit the ground); and after the second, when J.T.’s main enforcer, Price, is brought down by bullets, Venkatesh pulls him to safety inside the building.

On another occasion, he joins the building’s squatters in chasing down a young man who had just brutally assaulted his girlfriend. As the men intercept the assailant in a stairwell, Venkatesh unabashedly describes joining in on the beating that the man receives. Though such a deed would hardly pass muster at today’s university institutional review boards–which must authorize the research graduate students do with human subjects–Venkatesh succeeds in making vigilante justice seem reasonable in a world where police and ambulances don’t respond. Similarly, he shows how the Black Kings didn’t simply “take over” their buildings, like some kind of occupying army. Rather, they stepped into a void of power left by the reluctance of the police department, emergency services and various social agencies, all of which appear to have been too afraid or too scornful to address local needs. Venkatesh, via J.T., shows how violence and disorder are bad for business, explaining why gangs have a strong incentive to maintain the peace in these no man’s lands. J.T.’s gang “acted as the de facto administration of Robert Taylor: J.T. may have been a lawbreaker, but he was very much a lawmaker as well.”

Venkatesh recounts scenes of a sort that one would be hard-pressed to find in any other book. There’s the public forum to discuss gang violence, during which everything gets vented and nothing gets settled–until afterward, when the gang leaders settle their quarrel and shake hands in a small sit-down quietly brokered by a local minister and attended by a cop, Officer Reggie, who grew up nearby. There’s the near-lynching of a Middle Eastern store owner, who had sexual relations with the daughter of an angry local woman; J.T.’s lieutenant brokers an agreement involving cartons of free soda that keeps the store from being ransacked. There’s J.T. trying to expand his turf by pitching young would-be gangsters in Iowa with the zeal of an Amway salesman.

And there are several riveting encounters with police. Except for Officer Reggie, police in this account are generally absent from the projects. But on a visit to see Reggie at his precinct house, Venkatesh notices a flier for a party at a bar that was sponsored by J.T. and the Black Kings; Venkatesh was there when the affair was raided by a multiethnic group of masked men who stole all their cash and jewelry–cops, according to J.T. at the time. The flier is annotated with names, apparently like a sign-up sheet for those who planned to take part in the raid.

Reggie, asked directly, tells Venkatesh he’d be better off letting the matter drop because already other officers are suspicious of the young researcher. Reggie tries to help him by setting up a meeting at a bar between Venkatesh and a number of the men in blue, but it almost turns into a fight when one vituperative cop keeps repeating, “I know what you’re up to.” Later Venkatesh realizes, with trepidation, that he has seen this man before: shaking down a dealer in his apartment, leaving with a bag of money from the man’s oven. And the officer saw him. Not long after, Venkatesh’s car gets broken into and the contents of his knapsack are strewn about in a presumed search for notes and a warning to be careful.

That officer was a rogue cop. But is Venkatesh, as the subtitle has it (and as he, getting into the spirit of things, even refers to himself), a “rogue sociologist”? In some ways, apparently yes: sociologists these days spend a lot of time collecting data (a term Venkatesh even uses to refer to his field notes), which they then parse in ways that a math major would appreciate. The kind of qualitative, ethnographic research Venkatesh was up to seems less common these days, even though, as he notes, it was what made the sociology of the Chicago School famous in the 1920s and ’30s.

But in other ways, he seems decidedly not a rogue. The image he more consistently paints of himself is that of a graduate student keenly attentive to his father’s advice that “the key to success in graduate school would be to develop a good relationship with my advisers,” a graduate student who, for example, picks up the game of golf expressly in order to cultivate a relationship with his famous mentor. Venkatesh’s initial, reasonable impulse–to write a dissertation about this gang and its leader–is discouraged by Wilson and other professors, who steer him instead to study everyday life in high-rise projects. That would seem to explain why this book, which roughly describes a period from 1989 to 1996, wasn’t written until now: academia is the author’s first master, and there was other work to do.

Venkatesh admits, however, that he never really informs J.T. of this change in his marching orders. The gang leader, despite drawbacks (Venkatesh’s association with J.T. sometimes makes it hard, for example, for him to cultivate relationships with people outside the gang), “was certainly my best access” to the community. And so he uses J.T.–and J.T. uses him, though it takes the guilty-feeling Venkatesh a while to catch on to why. For example, to further Venkatesh’s study of the projects’ off-the-books economy, J.T. happily agrees to help him set up interviews with pimps, prostitutes, “all the people stealing cars” and more. And he introduces Venkatesh to Ms. Bailey, the book’s second great character. Ms. Bailey, a hard-boiled, heavyset older woman, augments her salary as building president (an elected, part-time position) by skimming off a percentage of the proceeds of unofficial business activities to which she turns a blind eye–the illegal hair salon, the illegal hamburger kitchen, the illegal daycare center–making her a gangster of a sort, as well. These men and women–many of them no doubt under duress–agree to talk to Venkatesh, who promises them he’ll keep the details confidential.

Unfortunately, and somewhat horrifyingly, he then turns around and shares what he learned with J.T. and Ms. Bailey–to verify the information, he says. Readers can see this train wreck coming a mile away, but the gormless Venkatesh doesn’t realize anything’s gone wrong until suddenly everybody he’s interviewed is giving him the cold shoulder. Many of them, it turns out, were making more than J.T. and Ms. Bailey presumed they were, and now the power brokers are shaking them down for a bigger share of revenues. In journalism, these people are called sources, and I have not read about such a massive, clueless betrayal of a source since Denis Johnson’s amazing, conflicted piece about the war in Liberia, published in Harper’s in 2000 and included in his 2001 nonfiction collection, Seek: to sneak into the country without proper credentials, Johnson hired local fixers–who suffered mightily when he offered up their names to the police as soon as he was caught.

The title of Venkatesh’s book refers to a stand-alone chapter that is a kind of set piece about a gang leader’s life. It starts like this: Venkatesh tells J.T. that he’s got it easy. J.T. says, Oh yeah? Why don’t you try it for a day? Venkatesh says, OK, I will.

It’s my least favorite part of the book because it’s gimmicky, a setup for a first-person telling of a day in the life of a crack gang leader. And it’s based on a premise we already know to be false: by this point, Venkatesh has spent pages detailing the perils and stresses of J.T.’s life: the risk of prison, the risk of death and injury, the risk of betrayal, the need to use physical intimidation, etc. Sure enough, as Venkatesh makes the rounds with J.T., his patron (sworn to protect him and disinclined to add uncertainty to a tenuous enterprise) doesn’t put him front and center but instead tells him to shut up and stay in the background. He’s hushed during a negotiation with a convenience store owner who won’t let Black Kings into his shop anymore; he’s told to sit in the car and look the other way when J.T. punches one of his salesmen in the face as punishment for withholding revenue.

I sense a marketer’s hand in the “gang leader for a day” conceit, as I do in the phrase “rogue sociologist” and the author’s pose in the photograph on the book’s cover: leather jacket, arms folded as though he’s the tough guy. Yes, we are all in favor of helping sociologists reach a general audience. But this book is exciting enough without trivializing the author’s work. Gang leader for a day? How about for years and years? Inside America’s largest, doomed housing project? And at the peak of the crack epidemic?

When you think about it, that first scary meeting with J.T. was the start of Venkatesh’s career. That was in 1989, and it is described in the book’s opening pages. Fast-forward to 1996, which falls near the book’s end. The Robert Taylor projects are soon to be torn down, J.T. is facing the prospect of dwindling sales (and unemployment) as his base of operations is demolished and an outdoor party sponsored by the gang is interrupted by a shooting. Life in this world looks as grim as ever. Space break, new paragraph: “In the spring of 1996, I learned that I had received a junior fellowship at Harvard’s Society of Fellows,” writes the young sociologist. “I was ecstatic; it was a much-sought-after position, a three-year salaried research post. I went to tell J.T. the good news.”

By Venkatesh’s telling, his main informant doesn’t take it too hard–he even offers to set Venkatesh up with a gang leader he knows in New Jersey. But the arrival of Venkatesh’s career news in this setting is a bit grotesque:

For a time I thought that J.T. and I might remain close even as our worlds were growing apart. “Don’t worry,” I told him, “I’ll be coming back all the time.” But the deeper I got into my Harvard fellowship, the more time passed between my visits to Chicago, and the more time passed between visits, the more awkward J.T. and I found it to carry on our conversations. He seemed to have grown nostalgic for our early days together, even a bit clingy. I realized that he had come to rely on my presence; he liked the attention and the validation.  I, meanwhile, grew evasive and withdrawn–in large part out of guilt. Within just a few months at Harvard, I began making a name for myself in academia by talking about the inner workings of street gangs.

Bringing up Harvard strikes me as a strategic error: Venkatesh could have just said he was leaving Chicago to do a postdoc. Instead, by sketching out his glorious trajectory, he encourages us to picture him in a paneled dining room, sipping sherry, while his erstwhile soulmate languishes in the ghetto. Within a few years, J.T. is done with gangs and is managing his cousin’s dry-cleaning business. Then he’s starting up a barber shop, which fails.

This is a peril of first-person nonfiction, which the author of a sociological study might not typically face: suddenly, the reader cares about the narrator’s relationships with the main characters. In fact, he will approach you after readings or send letters via your publisher or e-mails via your website to ask, Where is that person today? Are you still in touch? In his mind the story goes on–even if, in reality, it’s over.

Alex Kotlowitz, coming from a place of privilege, sagely and admirably ended There Are No Children Here by telling how he helped the Rivers brothers find a better school outside their neighborhood, and established a fund to help ensure their continued education and success.

J.T. was not so helpless, and Venkatesh makes it clear that J.T. used him just as he used J.T. (It takes a lecture from angry C-Note, a squatter whose income has just been divulged to J.T., for Venkatesh to admit that he was hustling in the projects just like everyone else, even if what he was after was information.) To his considerable credit, Venkatesh acknowledges feeling bad and seems candid throughout about his various missteps. Still, the divergence of the two men’s paths through life is a disconcerting note on which to end. Venkatesh (whose online CV lists grants received to study social ills that add up to more than $4 million) concludes his book by recharacterizing that “deep connection” and “strange intimacy” with J.T. that we heard about at the beginning:

It would be hard to call us friends. And sometimes I wonder if we ever were.  But he was obviously a huge part of my life. For all the ways in which I had become a rogue sociologist, breaking conventions and flouting the rules, perhaps the most unconventional thing I ever did was embrace the idea that I could learn so much, absorb so many lessons, and gain so many experiences at the side of a man who was so far removed from my academic world.

It’s a kludge of a final paragraph, the tone a bit reminiscent of a college admissions essay. Perhaps the author knows he has reached the less-inspiring part of the tale: the same dynamic that makes this story so exciting (hero enters a dangerous, unknown world, slowly gains acceptance) makes it hard not to end it with a whimper (hero moves on to better things, leaving friends behind). Give Venkatesh credit for doing something brave and difficult. Fault the world for the bitter ironies he exposes in his book, both intentionally and not.