Riding along with the people who help Philly's chronically homeless

James had ridden a bus for 30 hours, traveling to Philadelphia to find his long-lost brother. He’d come to ask for money and a place to stay, but after four days, James had gotten no further than the waiting room of the Greyhound station in Chinatown. Venturing out into the streets during one of this winter’s brutally cold nights, the 62-year-old had slipped and fallen, breaking his shoulder. After treatment in a hospital, he floated back to the bus station, with only a few dollars and his brother’s outdated address in hand, to try to recuperate.

I met James on a recent morning while I was shadowing Sam Santiago, an outreach coordinator for the homeless support agency Project H.O.M.E. James was slumped against a wall leading to the station’s men’s room, his wounded arm swollen. A bus depot manager, no stranger to people using his facility as a temporary home, had called Project H.O.M.E.’s outreach hot line after watching James’ last dollars slip from his pockets as he struggled to reach the restroom. It didn’t take much prying for James to open up.

“I’ve come a long way from Reno to find my brother,” he blurts out at Santiago’s first question, before admitting, sadly, that he isn’t sure if his brother knows he’s in town. They haven’t seen each other in 40 years.

Santiago has spent 14 years building relationships with people like James — chronically homeless individuals who often have had negative experiences with shelters and bureaucratic support systems. His expertise is in tracking and building trust with men and women who live on the city’s streets — a difficult process that can take years. 

Philadelphia is unusual for having a relatively small number of unsheltered people compared to many big cities, especially those in the West. Only one in 3,095 Philadelphians sleeps on the streets, compared to one in 254 in San Francisco.

Some attribute this to a more effective shelter system and, perhaps equally, to the harsher climate here. 

But it can also mean that those who do wind up on Philadelphia’s streets are  among the most challenging to support. Enduring cruel winters and the very real threat of violence is not a decision anyone would make lightly, and many who do also suffer from severe mental illness or substance abuse issues. It makes it that much harder to try to convince someone to come in out of the cold. But for James, tired and battered, Santiago’s offer of a warm place to lie down is an easy sell.

“Do you want to maybe go to the office and have one of my co-workers try to call your brother?” asks Santiago. “I’ve got my van right outside.”

I watch Santiago help James into a grey Project H.O.M.E. minivan. It’s only 9 a.m., and Santiago, who has been making his rounds since 6 a.m., has at least a dozen more people he wants to check on this day.

 Many people have a mental image of what homelessness looks like based on their everyday interactions: a man sleeping on a steam vent, or panhandling for spare change on a street corner. But homelessness, like its causes, varies wildly from person to person and city to city, and touches many people who don’t fit traditional stereotypes. Families make up almost as much of the population as single adults, and children are nearly as common as adult men. 

The vast majority of people who struggle with homelessness in Philadelphia, estimated at around 12,000 in 2012, move in and out of about 5,500 beds stretched across shelters and transitional-housing units across the city. Most are eventually helped back into permanent housing, with only about 4 percent, or about 500 people at any time, consistently living on the streets. Though the group of people Santiago is trying to reach has shrunk in recent years, it tends to be a very fragile demographic — they are older, with an average age of 51, and often have had bad experiences in traditional shelters.

The city is more than halfway through a 10-year campaign with partners like Project H.O.M.E. to “end homelessness,” largely through the construction of affordable-housing units. But the campaign is still about 1,000 units short of its goal. Traditional shelters and recovery programs are usually all that Santiago and other outreach workers have to offer.

“If all that’s available is a shelter and you have [had] a bad experience, you’re probably going to be less likely to do what Sam says the next time,” said Laura Weinbaum, Project H.O.M.E.’s vice president of strategic initiatives. “I have no question that we could get more people to come in if there were more good [affordable-housing] units with appropriate services available.” 

There is strong evidence that even chronically homeless individuals undergo transformative experiences when placed in permanent housing. One organization, Pathways to Housing, takes men and women off the street and puts them into subsidized-housing units, keeping tabs through regular visits. Known as a “housing-first” strategy, the group has recorded a 90 percent retention rate, versus about 50 percent in more traditional models.

“We’ve been really successful in working with this one really difficult population of people who are chronically homeless and have multiple disabilities and can’t live with other people,” said Christine Simiriglia, executive director of Pathways to Housing. “And, yes, there is a waiting list.”

Some homeless advocates wonder if it’s practical or even desirable to try to “end” street homelessness by fitting everyone indoors. They note that some people are only comfortable outside, and any housing-only plan would implicitly exclude this group from the “solution” to homelessness. But everyone I spoke to agreed on one point — without constant outreach, any strategy to address homelessness is futile.

 A little after 10 a.m., James is registering with staffers at Project H.O.M.E.’s headquarters in North Philly. Santiago is already back on the streets. He points the van toward a rail line along the Schuylkill where he has made contact with a group of younger homeless men. On the way, we stop at a bridge abutment that he knows has been an informal shelter in the past. 

It only takes Santiago, a 52-year-old man originally from Puerto Rico, a minute or two to inspect the abutment. He sees someone he knows, a man who is clutching a kitten and is asleep under a mountain of blankets. The man is not happy to be awakened by Santiago’s blaring voice, and I hear shouted curses as Santiago gets back into the driver’s seat.

“You tell me you’re a child of God and then you curse out your outreach worker. What is up with that?” Santiago says, chuckling to himself.

Santiago is an ex-cop, which sometimes shows in his sense of humor. What can seem like callousness is also a coping mechanism for the rejection he experiences from those who don’t accept his offers of help.

He never planned to be in this line of work. Badly injured when he accidentally flipped his police van during a high-speed chase, Santiago later worked for years as a private investigator. But the gigs were inconsistent, and during one dry spell his wife submitted his resume to Project H.O.M.E. without his knowledge, thinking his investigative experience would be a good fit for an outreach coordinator. She turned out to be right — Santiago says he’s served longer than anyone else on the outreach team.

Like any good detective, he pulls out his smartphone and jots down the date and a quick note about his last encounter. He keeps detailed notes on everyone he meets and I ask him how many entries he thinks he’s made over his years on the job.

“I engage about 10 or 15 people a day, so … ” he trails off as he thinks, then laughs. “Five days a week, times 14 years. Shit, that’s a lot!”

The van he’s driving jumps a curb, trundling over gravel next to the railroad. As a freight train passes a few feet away, he spies a group of three young men who have been camping out under a cave-like concrete overhang for almost a year. The area is ankle deep in trash and a tent that has collapsed is soaked with water dripping from melting ice overhead. The three are sleeping on exposed mattresses laid atop the refuse, not far from a popular jogging path.

He approaches this and every encounter with the poise of a police officer — slowly but confidently, keeping just enough distance until he’s assessed the situation and each person. The most violence he’s seen in his outreach career, however, was when someone threw a container of Chinese food onto his new sneakers.

“You guys hold up all right in that damn weather last week?” asks Santiago as he sizes up the camp. He’s referring to Tuesday, Jan. 7, when temperatures dipped to 4 degrees.

“Man, I woke up literally covered in ice. There were icicles in my sleeping bag,” says a young man named Rob, bundled in his sleeping bag, under a pile of blankets. “I felt like I died.”

I ask him why he’d rather risk the night outside than go into one of the city’s emergency shelters.

“Shelters aren’t really nice places in Philadelphia,” he says, without a hint of irony. “I mean, what — I should go to get my shit stolen or get in a fight?”

Rob’s companions are silent; one is deliberately avoiding eye contact and refuses to give his name. Santiago tries a quick, hard sell on the city’s recovery houses, but Rob insists he and the others only drink and smoke cannabis and don’t need that kind of help. After an awkward moment of silence, a dubious Santiago leaves a few gift cards for a local convenience store and promises to bring them extra blankets later in the day. It’s not much of an interaction, but it’s progress. The last time he approached, the men left to avoid speaking to him.

 The afternoon sun is starting its descent as we head crosstown to one of I-95’s many overpasses along the Delaware River, where Santiago has two clients he wants to visit. As we drive, he’s thinking back on the people he’s known over the years, but the stories are getting darker. He remembers one homeless man in his own neighborhood, Olney, named Donald. Santiago began to stop by after work to help, and one particularly nasty winter day, he found Donald with frostbitten toes. Santiago had tried taking him to different housing programs, but none stuck. He says he still thinks about the day his supervisor told him that Donald had been killed while crossing a street, back in their neighborhood.

“I’ve been doing this so long, I hear somebody died and I usually know who it is,” he says, as we cut down a side street that runs under the highway. “Some years are worse than others. Last year, I knew at least eight people who passed away.”

The van heads off to another overpass a little farther south along Delaware Avenue. Santiago leads me through a hole in a chain-link fence, and we are soon at the base of a massive highway-support column, traffic roaring overhead. Below are two shanties made out of scrap wood and bungee cords. A tiny image of the Virgin Mary is pasted on the column.

“Que pasó?” shouted Santiago, in the direction of the shacks.

A man named Alex, an immigrant from Guatemala, emerges bleary-eyed and smiling. He’s been drinking and is ecstatic to see Santiago, who had recently bought him a pair of winter boots. Santiago sheepishly accepts an embrace from the florid man.

Ramón, who is originally from Mexico, emerges from the other shanty, wearing a woolly jumpsuit. Santiago asks the duo how they’re feeling and they say they’re fine. Ramón says he’s trying to work and send money to his daughter in Mexico. Eventually we leave, as they cheerily wish us a nice day. But Santiago furrows his brow and mutters to himself.

“Alex needs to be in fucking detox. He’s a bad alcoholic. If he would have been out here on Tuesday …” he says, again referencing the day of single-digit temperature, shaking his head. 

Later in the afternoon, we drive to yet another overpass, this time deep in South Philly, where a man in his late 50s is sitting nearby, soliciting donations from people in passing cars. Robert has been panhandling here and living on vacant land nearby for six or seven years. He says he has no family left and stopped collecting disability some time ago, but appears to be otherwise healthy and happy. He proudly tells Santiago that he’s only spent one day indoors all winter, that fateful Tuesday that so many have mentioned, and has stayed warm under a pile of 30 blankets. He says someone, possibly the city, demolished a shanty he’d constructed nearby. He rebuilt it.

“Shelters aren’t for everybody. I’m not into all that alcohol shit,” he explains to me, referring to the common stipulation that shelter residents refrain from using drugs or alcohol. 

“But look at me. I have some bad days, but I’m all right,” he says. “Anyway, Sam looks out for us, and he’s good people.”

Santiago is silently embarrassed again. Robert notices and smiles.

“He paid me to say that,” he says, erupting in laughter.

 The afternoon ends back at Project H.O.M.E. headquarters. James is still there, not far from where we left him. He is asleep, still waiting to be placed.

Staffers have, amazingly, located his brother, who still lives in Philadelphia. But the man wants nothing to do with James, who he says has been a drug addict since he was a teenager. He offers to buy him a bus ticket to anywhere else. Santiago is nonplussed.

“I’ve seen how manipulative people can be, especially when they’re using,” he says, and cautions that it’s pointless to judge unknown relatives who may have spent years fruitlessly struggling to help someone.

Santiago is more focused on how to treat James right now. He’s gotten him through the door, which is a big step for some, but still just the beginning. Word comes through that there is probably a temporary bed open at a group facility geared to elderly homeless men, but, of course, there’s no telling if he’ll be happy there.

As for Santiago, his work day is nearly over and the pattern of suspicion and rejection he faces has revealed itself clearly. I ask him what keeps him going.

“I just saw a guy who’s been drinking since I’ve known him, 10 or 15 years, and now he’s staying at the [VA hospital],” he says. “I’m not going to say he’s stopped completely, but … ”

He trails off again, almost sounding unconvinced himself, but then he starts to recall other people who have made the transition. He remembers a man named Luther, whom he worked with for 11 years on the streets, and who’s in an apartment now. And he mentions the letters he’s gotten from other people who have turned their lives around and realized that the process started with him. 

He thinks about a son, who is schizophrenic and whom Santiago says he sometimes sees reflected in the young people he encounters on the streets. He thinks about the people he’s met who were once just like him — grown, with a career, with a family — who lost everything. Who would be there to help him or his family if they were in the streets?

“The problem is that city officials think sometimes you’re going to engage and it’s going to happen right away,” he says. “Well, shit don’t work that way.”