Portrait of a man sitting on a couch.
Zengzheng Wang

The first encounter was on a cold Autumn afternoon in 1989. A woman carrying two bulky bags over her shoulders caught the attention of legendary journalist Gay Talese as she stood on the corner of Lexington Avenue and Fifty-Ninth Street in New York City.

She appeared to be in her early forties, with delicate bones, blue eyes, and short curly blond hair. Talese continued on his way, but the image of the woman stuck with him. A few blocks later he turned around and walked back to ask her an awkward question. “Are you a homeless person?”

The encounter was striking. Her appearance wasn’t that of the stereotypical homeless person and neither was her story. She was a married hair stylist who once owned her own salon. Her husband lived in Queens with their three children in one of the two homes they bought together. The other was in the Pocono Mountains of Pennsylvania. But she left it all behind for reasons she didn’t say.

Talese wrote about The Homeless Woman with Two Homes in New York Magazine and it was recently republished in his latest book, “High Notes: Selected Writings of Gay Talese.”  While her story was unique, he also noted at the time that “urban destitution and despair are now spreading to the degree that identifying their victims visually is often impossible. Increasingly, the victims in our streets are looking like the rest of us.” It was the first time Talese, famous for defining literary journalism with his profiles of Frank Sinatra and Joe DaMaggio, had spoken to a homeless person so directly. But it wouldn’t be the last.

Talese has since gotten to know some of the homeless individuals near his third-floor apartment on the East Side of Manhattan, where he has lived with his wife Nan for almost 60 years. One such person panhandles in front of a bakery two blocks from his house. Another is on Madison Avenue.

“There are people that have been in my area who have been here for years,” Talese said in a recent interview with Street Sense. “There’s certain streets that I know certain individuals. You see them there, it’s their turf.”

He sees them as businesspeople who are just trying to make a living.

“When you see a business from year to year still located in the same place, you have to say they’re doing business,” Talese said. “Whatever it is they’re selling, it’s selling enough they’re paying the rent. Well, when you see the same faces soliciting funds with their hand out begging for a dollar, or maybe settling for less, they must be doing enough to keep themselves from starving to death.

“That’s not a comforting thought,” he said.

In 2009, around the height of the great recession, Talese decided to lend his writing skills to some of the panhandlers in his neighborhood by helping them make their cardboard signs more timely and attention grabbing.

He had been on his way to cash a check on Madison Avenue when he stopped to ask a panhandler, “How’s the economy affecting you?,” Talese wrote in his column for the New York Times.

“No different,” the panhandler said. “It’s always lousy.”

Later, Talese saw another panhandler, this time with a sign that read “Homeless. Please Help.

“I dropped a dollar into his container, but at the same time thought that the sign might benefit from updating — it needed a touch of stimulus, that word that dominates the headlines,” Talese wrote in his column.

He pulled out a strip of laundry board and wrote: “Please Support Pres. Obama’s Stimulus Plan, and begin right here … at the bottom … Thank you.” The panhandler promised to copy it to his sign the next day.

“The next day, on Sunday, and during the Monday holiday as well, I handed out these boarded messages at random to people who approached me for money, explaining why I thought their economy would be stimulated by my street signs,” Talese wrote in his column. “I further pointed out that the big bankers and industrial leaders the government was bailing out had lobbyists and public relations companies doing their bidding; but these wandering men who were seeking handouts in the street had to tap into the topicality of their plight, had to link themselves into the headlines and the top priority of President Obama. Stimulus, stimulus!!”

He later went back to see the panhandlers he had given signs to.

“Some of them said they had a lot of conversation with people, Talese said. “They saw this sign and it was different. And this prompted conversation. So those people, seeking whatever kind of financial help they could get, were not faceless.”

One of the reasons homeless people have become faceless is because they don’t have anyone to represent them, according to Talese.

“The people that are homeless are very often quiet people,” he said. “They don’t have lobbyists, they’re not organized in a union, so they don’t have a spokesperson, you don’t know about them, and sometimes they don’t want you to know about them either because they have their own shame, and their own secrets, and their own willingness or their own eagerness to be divorced from others.

“They are in the shadows of our vision,” Talese said. “And because they don’t offer us any reward for caring, they don’t increase our sales, they don’t increase our ratings or give us hits… they represent nothing that’s desirable. And so, they go from generation to generation, generally, unrecognized in any meaningful way.”

Talese believes homelessness should be a bipartisan issue.

“I don’t care whether it’s an Obama world, or a Trump world, or George Bush, or whoever the president is,” heTalese “There’s no excuse for how little regard and humanity is shown to people who have lost their way.”

Especially in a city as wealthy as New York.

“I have seen how sad the city is in the shadows of some of its churches and some of its stores along main avenues in the afterhours from six, or seven, or eight o’clock at night — especially in the warmer months,” Talese said.

“The city of New York, with all of its money, shouldn’t have those sights,” he said. “They’re the result of our own greedy capitalism and our lack of heart as a democracy.”

As for the person he wrote about in The Homeless Woman with Two Homes, Talese called several salon owners he knew and hoped to get her a job, but he never heard from her again.

“She said she’d call me, I gave her my phone number, and I then called these people before she was supposed to call me back, and they said ‘yes they’d be glad to see her [and] offer her a job if she was as qualified as I thought she probably was,’” Talese said. “She never called me back.”

Homelessness has skyrocketed in New York City in the years since Talese wrote about the homeless woman with two homes. Over the past two decades, the homeless population living in the city’s shelter system has increased 115 percent, from 23,868 in 1994 to 60,000 in 2016, according to the New York City Department of Homeless Services shelter system census.

For most New Yorkers, Talese said, homeless people “are considered an inconvenience.” It’s an observation he made nearly 30 years ago, after he took the time to get to know a homeless woman at Lexington Avenue and Fifty-Ninth Street.

“These mysterious people live among us each day, sleep at our door, walk shoulder-to-shoulder with us on the street,” Talese wrote in The Homeless Woman with Two Homes. “Yet, regrettably, we do not know them, and too many New Yorkers, with the donation of a few quarters daily, are able to buy their way out of whatever momentary concern or discomfort is caused by the presence of the homeless.”