Their conversations invariably begin with small talk: Where did you grow up? What high school did you attend? How long did it take you to grow that mustache?

Before finally: Would you consider accepting shelter?

Since August, a group of roughly 25 volunteers, including those who were once homeless, have been applying this delicate approach when speaking to people living on the streets. The volunteers' goal is offer people a way into the city's shelter system by building trust — never through coercion.

Known as the Street Homeless Advocacy project, the effort is the brainchild of civil rights attorney Norman Siegel, a longtime critic of city government but ally of Mayor Eric Adams. The initiative, which is premised on securing consent, began four months before Adams floated a plan to forcibly move people believed to be mentally ill into hospitals.

As a result, the project has become both a counterpoint to the city’s position and a test of Siegel’s 30-year friendship with Adams. Over that time, both men have rallied around a host of seemingly intractable issues ranging from police brutality to affordable housing, but have disagreed on how to best address homelessness and mental illness.

But the group has showed promising outcomes so far. Volunteers have successfully engaged with around 380 homeless New Yorkers, according to Siegel. Of those, 116 agreed to accept the offer of a bed in a non-congregate shelter. That amounts to a more than 30% success rate.

The 79-year-old has represented a long list of underdog clients: homeless New Yorkers, Adams when he was an outspoken NYPD captain, public housing tenants, individuals fighting redevelopment,  and even Gothamist during its blogger days.

But Siegel now finds himself in unfamiliar territory.

“Most of my career has been being the outsider,” Siegel said. “But now there's an opportunity for me to be a little in the inside, have some access, but also still be who I am, which is the outsider, the gadfly, the troublemaker causing questions that need to be raised.”

Siegel, who formerly led the New York Civil Liberties Union, argues the mayor’s approach is not only bound to fail due to a lack of sufficient mental health services, but also violates the constitutional right to liberty.

The plan also offends him as an ‘out of sight, out of mind’ way to ease the public’s feelings of discomfort and fear toward homeless people.

...Now there's an opportunity for me to be a little in the inside, have some access, but also still be who I am, which is the outsider.
Norman Siegel, civil rights attorney

He says he has made his objections known to the mayor and his advisers.

But even as he has criticized Adams' plan for tackling street homelessness, he has run his volunteer outreach group with the mayor's backing. City Hall provides him with a space to hold meetings, additional staffing from the city’s Department of Homeless Services and a way to transport people immediately to shelters once they accept the offer.

Prior to going out every Thursday night, Siegel obtains a report from the Department of Homeless Services on the count and location of single and multiple occupancy beds available in the city’s shelter system. The number for the city’s Homeless Joint Command Center, which monitors city streets and coordinates assistance, is saved in his cellphone.

So is the phone number for Adams, with whom he regularly speaks.

Adams, who can be defensive when criticized, speaks warmly about Siegel despite their stark differences on this issue.

“Rooted in what we are doing is love,” he said in an interview with Gothamist. “And when you love someone, you know that you're going to disagree with them sometimes.”

The mayor added: “We're both moving in the same direction. He's using a different road than I am using. But if he gets there first, we're going to adapt to his plan completely.”

Rooted in what we are doing is love. And when you love someone, you know that you're going to disagree with them sometimes.
Mayor Eric Adams

There are signs that the city has since backed away from the original plan to involuntarily remove people from the streets. Last month, Adams notably made no mention of forcible removals when he released what he called the second phase of his mental health plan.

Earlier this week, an NYPD official shared data with the City Council showing the number of people that have been involuntarily transported to hospitals after being suspected of having mental illness through mid-March is lower compared to the same period last year.

Siegel is now focused on expanding the number of volunteers, which he hopes to grow to at least 100. On Sunday, the group will hold a recruiting event at NYU that is open to the public. The outreach comes as a coalition unveiled a campaign called “We ❤️ NYC” aimed at inspiring civic pride and volunteerism.

Volunteers receive a three-hour training. Those who have enlisted come from all walks of life, including advocates who are well versed on city policies and at least five people who have or are currently experiencing homelessness.

Siegel is not blind to the mammoth challenges of a housing problem that costs the city more than $3 billion a year in shelter services. Every week, the volunteers share the systemic and emotional obstacles they encounter in convincing people to leave the streets.

Their responses will come as no surprise to advocates. What works: single rooms. What doesn’t: congregate shelters.

But on a recent Thursday, there were only seven single rooms available.

A lack of identification can be another hurdle, as is the rule that a homeless individual can bring no more than two bags into a shelter.

The group is beginning to track outcomes by getting homeless people to sign a waiver that allows volunteers to inquire about them once they enter the city’s shelter system. Siegel has also pitched a plan for the city to use eminent domain to seize vacant hotels.

Siegel said he has told the mayor that he believes New York City can be a national leader on the issue of homelessness.

Last Thursday night at South Ferry Terminal, Siegel was joined by two other volunteers. Patrick O’Connor, 17, from Long Island, said he was referred by his father, a friend of Siegel’s. Jamal McLeod, 52, had recently been homeless himself.

McLeod often led the conversations, which could last as long as a half hour. By 9 p.m., they had succeeded in getting one individual to accept shelter.

One 63-year-old man initially tried to wave them off and suggested he was not worth their time.

“I’m a bum,” he said.

“No. You’re a human being,” replied an emotional McLeod.


New Yorkers looking to volunteer with the Street Homeless Advocacy Project should email: [email protected]

The NYU event on Sunday will run from 2 p.m. to 5 p.m. at the Silver Center in room 206.

This story has been updated with outcome data reported by the Homeless Advocacy Project.