THE CITY'S MOST recent census counted 6200 homeless people in Boston. On any given night more than 200 choose to stay out on the street. But then, choose isn’t really the right word. Many are so indentured to booze that they cannot, physically, go more than a few hours without a drink; the Pine Street Inn, along with other area shelters, prohibits alcohol on its premises. Others suffer from mental-health problems that leave them reclusive and distrustful of authority. Others still simply cannot stand the mayhem that inevitably greets them at the city’s overflowing shelters.

Tonight, there will be almost 600 bodies competing for Pine Street’s 400 emergency beds. And while no one will be turned away, only those lucky enough to score a bunk during one of the Inn’s twice-daily lotteries will get anywhere near a decent night’s sleep. The rest will find themselves on mats or cots or on the bare floor in the laundry room or the dining area or one of the corridors. They will spend the night being stepped over, talked over, buffeted by cool breezes, and dazed by fluorescent light. Some of the men (homeless women are accommodated at a separate shelter next door) sidle up to a dormant washing machine, to feel the residual heat. Mostly they sprawl, in every available spot, in every conceivable position, as if they have fallen from a great height. It is, to say the least, a situation that is not conducive to peaceful slumber.

The lotteries themselves are near riotous, a clamor of jeers and whoops and groans. The men gather by the hundred — like a "herd of cattle," says one worker — in an area called the Cage. Here, they jostle and strain before a small window, where a man reads names pulled from a plastic bin. "Relax, gentlemen! Relax!" cries a worker named Bill Greene, whose role seems to fall somewhere between counselor and security guard. "He’s dead!" shouts one man as a name gets no response. "He’s under the bridge!" yells another. "Bridge party!" hollers a third, and there is laughter. Occasionally, a bed-winner will be too old or too infirm to push his way to the front of the line, and his ticket will be passed back to him.

And yet, though a feeling of fellowship does exist during the lottery, so too does a feeling of anxiety, even rancor. The death of Bob Gurney, says Greene, hit these men hard. "They’re upset," he says. "We’re all feeling bad." As the roll call continues, a guy at the front of the crowd directs his frustration toward the Inn. "It’s all about the funding," he spits. " ‘Oh, come in, come in.’ " Eventually, the man gets into a spat with another guest, and it threatens to become physical. When Greene tries to take the disgruntled man aside, he becomes abusive, violent. "It’s bad, baby, bad," says an onlooker. "A jungle," adds another. It’s hard to say whether they’re being funny.

On particularly cold days, Pine Street offers amnesty to those who have previously been barred — for drinking or fighting or possession of drugs or weapons. Yet the Inn takes a hard line toward violence. "You can’t have absolute chaos," says Gaughan. "If people got hit at will, they wouldn’t come in." And so the man who fought with Greene is ejected. Out.

The lottery continues: five beds left, then four, then three, then two, then one. At the end, most of the men shuffle away. But a few stick around to cajole, bicker. One, an old black man, stands stock-still, staring, as though he can’t believe his luck. All this for a scratchy blanket, a plastic mattress, and a hall filled with hundreds of snoring, hacking, sweaty bodies.

Even those who work the outreach program admit they have a tough sell on their hands. "Obviously, you want to get people in, to save lives," says Gaughan. "But you have to be realistic. You’re taking people into a situation that is not going to be good for them. It’s noisy. It’s chaotic. It can be self-defeating to encourage people to take advantage of already-overburdened facilities. It can be confusing for them, irritating, frightening."

The quandary the outreach teams face, then, is how much pressure to apply to those who refuse shelter. "We have to respect people’s self-determination," says Gaughan. Now and again, an outreach worker will call 911 — if someone is so intoxicated that he or she is deemed incapable of making decisions, for instance — but to do so for every at-risk homeless person would place a crippling burden on the city’s police and medical services. Also, there is no law in the state that authorizes placing the homeless in protective custody — so even if people are taken to a shelter in a "blue-and-white taxi," they can turn around a minute later and walk out. As Gaughan puts it, "We have no authority to force someone to come in."

Tony, a 38-year-old Boston native who’s been homeless for 10 years, is one of the 200-plus who refuse shelter. Standing on a downtown corner, Tony says he would sooner sleep in the vestibule of an ATM, or wander the streets, than join the crush at Pine Street. "Sad as it may be, you get accustomed to it out here," he says, hopping from foot to foot. "You want to get off the street. You want to be comfortable. But I’ve been out here so long, I feel at home." Frankly, Tony doesn’t look very much at home. Where exposed, his dark skin is chapped white. The area around his nose and mouth is flecked with mucous. His eyes are bloodshot, flat. Still, he says, "I’d rather be out here than in there tussling, everyone pissed off."

For people like Tony, the only thing standing between them and serious trouble is Pine Street’s outreach program. "Most of what I’ve got, I got from those guys," he says, holding out a fistful of the grubby woolen blanket wrapped around his shoulders. "Without that van we’d be hurting real bad." But there are those, like the people behind the BPL, who shun the OV altogether. "I don't deal with no vans," says a guy named Robert, standing outside Store 24 in Kenmore Square. "I can be a bum by myself." And Vinny Phillips, despite his determination to reach out to these people, understands why. "When I was a homeless person in the South End," he says, "I used to like the alleys. People were afraid to go there."

Like many of Pine Street’s workers, Vinny Phillips, 53, was once a "guest" at the Inn. A Native American, he sports long dark hair and aviator-style glasses, smokes heavily, and has a sardonic, cheeky sense of humor. Because of his history, perhaps, he moves among the people he serves with an ease that few of us could muster. And you sense that they appreciate this more than anything — there’s little in the way of woe-is-you about him, and this has a humanizing effect.

Indeed, one of the most impressive — and heartening — things about Pine Street in general is the way its staff interacts with clients. "Good morning, Mr. Johnson!" you’ll hear. "How are you?" There is gentle ribbing, even playful flirting. Some of the workers have been here for a decade or more, as have some of the guests, so there is a history between them, something approaching friendship. For people who, for the most part, move through the city like ghosts, this personal acknowledgment, the acceptance of them as human beings, is as crucial to their survival as the beds, food, medical care, and clothing Pine Street provides.

Spend any amount of time at Pine Street, and it quickly becomes clear that this kind of dignity is a prized commodity. Though there are many who fit the Homeless Man stereotype — the sagging jeans, the matted beard, the booze-blotched skin — many more are well turned out: neat clothes, clean-shaven faces, cell phones clipped to belts. There is a sense — shared by all of us to a greater or lesser degree — that to be homeless is to be somehow less than human. And so there is a kind of defiance in every scrubbed pair of jeans, every morsel of food wiped carefully from the chin, every spotless pair of sneakers. See? they seem to be saying. We are just like you.

Vinny Phillips, meanwhile, treats his clients with respect no matter how disheveled they look. At about 3 a.m. on Mass Ave near the Berklee School of Music, we encounter a man who, it must be said, is frightening to look at. He has a hood pulled up over his head, a thick, jaundiced-white beard, and, most ominously, a pair of shades obscuring his eyes. "How you doing, Simon?" Phillips asks, as though addressing a next-door neighbor. For the next few minutes, he rummages through the boxes in the back of the van, searching for a pair of long johns Simon’s size. "I told him we had some," he says. "I made a liar out of myself."

For the most part, Phillips and his crew keep things lighthearted. In the van, between stops, they crack jokes, swap anecdotes about clients, or sing along to the radio. Occasionally, though, the gravity of the situation seems to weigh on them, and there are periods of silence. At one point, having a smoke on the Commonwealth mall, Phillips’s upbeat, matter-of-fact approach to his job starts to show a few chinks. "He likes chicken soup," he says, gesturing at a plastic tarp, home to an aged, long-term-homeless man. "I told him we didn’t have any." He takes another drag on his Marlboro, then looks around at the grand brownstones lining the mall, their windows glowing warmly in the dark.

"These people don’t want the homeless here," Phillips says. "But [the homeless] never do anyone any harm."

Indeed, homeless people are far more likely to be assaulted than to commit assault. "I would say that someone living on the street is more at risk than someone walking by that person," says Eliza Greenberg, director of the Boston’s Emergency Shelter Commission. "There is a culture of disdain and contempt for the homeless, and that can play out in the way they’re treated on the street."

The homeless are especially vulnerable to late-night revelers: drunken college brats, bellicose suburbanites, urban thugs. "That’s what I worry about with these guys," Phillips says. "They’ve got nothing better to do than mess with the homeless." He recalls one night when a couple of drunks began to torment one of his clients.

"How does it feel to be poor?" one of the drunks yelled.

"How does it feel to be an asshole?" the homeless guy responded.

And then there are those who resort to more practical weapons than words. "There was this [homeless] guy named David," Phillips says. "I couldn’t go near him because he had a machete."

Homeless people may be vulnerable, but this doesn’t, of course, make them angels. Occasionally, internecine squabbles among the homeless themselves will turn ugly. Walking through a particularly blighted spot, next to Storrow Drive, Phillips points out a charred patch of ground. "They got into an argument about drugs or something," he says. "Burned each other out."