A Truck Full of Money (24 page)

On a late summer night in 2014, Paul boarded a van outside the Pine Street Inn, Boston's largest homeless shelter. There was a lot of stuff inside the van—jerry cans of hot soup, boxes full of sandwiches, hampers of clean underwear and socks. So the seating was a little cramped in the rear, where Paul sat asking questions of his guide, a doctor named Jim O'Connell.

The light and shadow of the city washed across the windows and the faces in the van. Paul leaned toward Dr. O'Connell, murmuring “Inter-esting, inter-esting” as the doctor spoke. For years Paul had been copying his hero Tom White and giving money to programs for the homeless. Lately, he'd been thinking that he should give more. Tonight he was doing research. He'd been told by people he trusted that if he wanted to know about this problem, he had to meet O'Connell. The doctor was sixty-five. He had spent the past thirty years ministering to homeless patients while helping to create an organization—Boston Health Care for the Homeless—and a host of facilities just for them, including emergency shelters, a walk-in clinic, a residency program at Mass General, and a respite hospital with 108 beds.

The doctor told Paul that eight thousand people were homeless in Boston on any given night. Most were housed by the city in motels or shelters, but about three hundred lived on the streets: “In England, they call it sleeping rough.” Vans from the Pine Street shelter had been visiting Boston's rough sleepers for thirty years.

The van wound through downtown. Some stops were brief, Paul watching out the windows as the doctor and the driver's assistant climbed out to check on people sleeping in the city's crevices. They lay under small heaps of blankets on sidewalks, in the doorways of shuttered businesses, on loading docks. Paul watched as the doctor approached them with his flashlight and called to the sleepers by name, saying, “It's Jim O'Connell,” and groggy faces, usually smiling, hair in tangles, emerged from under the blankets.

The van made longer stops at sites where crews of homeless people had camped for months and even years. When the van pulled up at these after-dark encampments, Paul got out and watched as little groups, mostly men, came out of the shadows, the van's driver and his assistant offering them the soup and sandwiches, the underwear and clean socks, while a woman named Robyn, a friend of the doctor's along for the ride, was dispensing Dunkin' Donuts gift cards. These, she explained to Paul, conferred the right for the homeless to use the restaurants' bathrooms—“the right to shit,” she said. Paul listened in as the doctor chatted with his patients, checking their medications, urging them to come to the walk-in clinic at Mass General tomorrow. It seemed to Paul the doctor knew all of them, and they knew him: “He's a homeless whisperer,” murmured Paul.

At one stop Paul found himself facing a row of benches beside Fort Point Channel, right across the water from Blade, the purple lights in its windows stretching across the darker water. Reflexively, Paul wondered,
Did they do this on purpose?
Would a plea for a donation follow? None did. When Paul pointed across the water at Blade and said, “That's where I work,” the doctor was clearly surprised. This was a favored nighttime refuge for the homeless. It had benches, sea air, and one of the city's few public bathrooms not far away, inside South Station.

Stop followed stop, each with its streetlamp-lighted images of misery. There was a psychotic woman with frightened eyes wearing a knapsack—“She's terrified of men,” the doctor said to Paul. “If I get near her, she'll start screaming.”

In front of a defunct bar called Hurricane O'Reilly's, there was a man with a wispy white beard in a wheelchair who was living out old age on the sidewalks, fending off various lethal ailments with a small pharmacy of medications that he kept in a plastic bag. A garrulous, gregarious fellow who said he used to be lead singer in a band and, to prove it, sang a song for the doctor and his company. Paul listened with his arms folded on his chest, in him a pose of unease; when the man finished, Paul lifted his hands and applauded softly.

There was a boy who came suddenly, silently, out of the dark reaches of a street and into the pool of light surrounding the van. The boy wore jeans, sneakers, a black jacket, a black baseball cap, a black knapsack—all as if, it seemed to Paul, he meant to make himself invisible. And why wouldn't he, given what Dr. O'Connell had said about how people prey on the homeless and how the homeless prey on each other? In what seemed to Paul like one fluid movement, the boy swooped in toward the rear of the van, grabbed a sandwich, and glided away, and by the time Paul thought of trying to talk to him, the boy had disappeared back into the shadows.

Homelessness rounds for Paul tonight were like viewing his hometown upside down. People wrapped in blankets sleeping on benches over at Fort Point, right across the water from the place where he hoped to start successful, if not billion-dollar, companies. People who lacked the right to shit making camp two blocks away from the lighted skyscrapers of the Financial District and the huge rectangular plinth that houses the New England branch of the Federal Reserve. To survive without a home required technique, like woodcraft, it seemed—knowing how to let oneself into temporarily vacant places like ATM lobbies, knowing where to find a bathroom and a modicum of safety, knowing where to hide one's gear, knowing when one had better leave a sanctuary in the morning. From his early teenage years, Paul had the freedom of Boston's streets. He remembered the time when a gang of kids tried to run him over, and the time, late one night near City Hall, when he was mugged, a knife at his throat. Where would that boy who swooped in for a sandwich hide when, in a few months, these streets were transformed into alleys between snowdrifts?

A hopeless feeling began to settle on Paul. It was frustrating for an engineer to look at things that were hard to fix. What were the causes of homelessness? he asked the doctor, in between stops, in the back of the van. Bad luck for some, the doctor said, and for most others, alcoholism, drug abuse, mental illness, dreadful childhoods. Couldn't something be done at least about the substance abuse? Paul asked. The doctor replied, “Those who got sober, I can almost name all of them over thirty years, and almost all of them had lives before. Most of the people we've met tonight never worked.”

What would O'Connell do if he had the resources to launch a grand antihomelessness campaign? The doctor answered in stages, between stops. Of course he had ideas about how some of the problems might be lessened, and he would welcome the chance to try them, but he tended not to dream big, not from day to day. He didn't let himself. The root causes of homelessness were old and various, and included, on the national level, a skewed economy and an indifferent government—a constellation of causes that lay far from a cure. “But,” the doctor said, “the clean socks we can do.”

Not long before midnight, the van stopped beside a little park, Curley Park, half a block from Faneuil Hall and near Quincy Market. It was a tourist spot by day. At night it was occupied by several of the doctor's patients.

The park's benches were arranged in a semicircle around a lifelike bronze statue of James Michael Curley—congressman, governor, and four-term Boston mayor, a child of Irish immigrants who had remained immensely popular among the city's working class, even while serving part of his fourth mayoral term in prison for bribery. Paul's grandparents had probably voted for him. Yet another statue of Curley was seated on one of the benches. The light was dim there, but there was enough of it to see the bronze mayor frozen in a pose clearly meant to suggest that he was talking to whoever was sitting at the bench's other end. Just now, that person was a man called Bobby No Shoes, who was conducting a spirited but incoherent argument with the statue when the doctor approached, Paul following.

A lanky-looking figure was sitting on one of the other benches—alone and with his head bowed over his knees. When the doctor introduced Paul, the man looked up, and in the dim light Paul could make out the gaps where the man's front teeth should have been. Paul thought the guy looked scared. His clothes looked clean, though, and when he spoke, it was clear that he was sober. He said his name was Tim.

Tim. It gave Paul a start to hear his brother's name assigned to a man living on a bench.

Paul sat down beside him and asked how he was doing tonight, and Tim said he was okay but tired. Starting a little before dawn and for about three hours a day, he delivered newspapers downtown. But he didn't make much, not nearly enough to have a place of his own.

Did he know the other people in the park tonight? Paul asked.

Yes, they were drunks, Tim said. And there were some others here tonight he didn't know. He didn't like it when there were strangers around. He didn't feel safe with them around.

It must be hard to live out here, Paul said, and Tim replied that he'd been given an apartment for a while, but he'd had to share it with a roommate. “That didn't work,” Tim said. He added, by way of explaining why he was living in the park, “I'm not a shelter guy.” And then, after a little more quiet talk, Tim said he was “bipolar.”

“I'm bipolar, too,” said Paul. “Whatever bipolar means.”

Over on Mayor Curley's bench, a very drunk woman had joined Bobby No Shoes. They were sitting with their arms draped over each other's shoulders, laughing raucously about something, their voices mingling with music from across North Street. There was a row of bars and restaurants over there, with lighted signs of varied colors in their windows and over their windows, a festive array, which made you think of lighted Christmas trees standing in the dark. The night obscured a great deal. In the half-light of the little park, the hard times recorded on Tim's face were mostly hidden.

Paul was having long thoughts: What flavor of bipolar afflicted this guy Tim? Maybe Tim's variety had caused him to do something bizarre periodically, something that had got him fired over and over again. A person could do some odd things when hypomanic, Paul knew, and they were things that would get you fired from a lot of jobs more quickly than from software engineering. Sitting on the bench beside Tim, Paul thought about a remark that a few friends of his had made over the last two years. When Paul had told them how uncomfortable he felt about his Kayak fortune, several had replied, “You shouldn't feel that way. You worked hard for your money.” The implication Paul heard was that poor people wouldn't be poor if they weren't lazy.
But I didn't actually work that hard,
Paul thought.
I'm just good at something that makes a lot of money.