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Meet The Man Helping To Shelter Mid-City's Homeless

Linda Pennington
In this undated photo, homeless outreach specialist Jessie Angeles Jr. kneels in front of a makeshift shelter in a City Heights canyon to speak with its homeless resident.

Erin Papaleo knew she’d be homeless after multiple surgeries put her out of work and she couldn’t pay her $900 rent. She figured she'd save money by living on the streets for just a few months. That was more than two years ago, and the associate’s degree holder is still sleeping beneath North Park storefronts.

"My thinking at the time was very naive," Papaleo said.

Papaleo is part of the homeless community living outside San Diego's downtown region and away from its large concentration of shelters and services. To help her and others living on San Diego's mid-city streets, a coalition of community organizations and representatives is bringing resources directly to them.


The group of business organizations, nonprofits and elected officials tapped Jessie Angeles Jr. to serve as a homeless outreach specialist in the City Heights and North Park neighborhoods. Angeles' job is to regularly roam hot spots in the communities and offer assistance to those living without a home.

VIDEO: Meet The Man Helping To Shelter Mid-City's Homeless

"North Park and City Heights — there’s limited amount of resources that can assist people that are experiencing homelessness," said Angeles, who is employed by People Assisting The Homeless, or PATH.

Since beginning the gig in January, he travels along the streets and into the area's canyons to offer snacks, toiletries and a range of services. He can help homeless individuals get an ID, food stamps, health insurance, cash assistance and hopefully a spot in a housing program.

While he's not the first outreach specialist to venture into the neighborhoods, he is the only one who visits the same areas over and over again. He said that's made him a familiar face among the skeptical community, even to people who aren't initially interested in receiving aid.


"It’s mainly planting the seed, the idea that the services are out there for them and when they see me again, they’ll ask me, 'How can I get there?" he said.

That's how it worked with Papaleo.

Tarryn Mento
Erin Papaleo wears a found Slayer T-shirt with a plaid flannel top while sitting outside a North Park coffee shop, March 7, 2019.

"It wasn’t until I think the second or third time that Erin actually went up to me and was like, 'Hey, I want help,'" Angeles said.

Papaleo is now one of his 23 clients. She said before meeting Angeles, she struggled to navigate the network of resources on her own, especially over the phone.

"You’re probably going to call that first number, maybe spend however long on hold, talk to somebody for a few minutes who's going to give you another number and probably about four or five phone calls later, you’re going to end up with that first number again," she said.

Angeles agreed the process can feel overwhelming.

"Even working in social services, it’s frustrating to contact another service provider and get in contact with the right person," he said.

After connecting with Angeles, Papaelo is just steps away from securing a bed in a housing and treatment program in North County. Angeles helped put her on the path by traveling with her to the DMV to obtain an ID — a document he said people on the streets are often without. With identification, Papaleo can access Medi-Cal to become eligible for the opportunity in Oceanside. At the same time, Angeles worked the phones on her behalf.

"I’m actually calling the facility trying to find a point of contact so we can set up an appointment for a screening time," he said.

He hopes to have her under a roof within the next couple of weeks. If so, she'd be the third person he connected with a housing opportunity.

Angeles will be on the job for at least one year. Funders will examine the results of an impact study to determine if they'll fund his position again.

Tarryn Mento
Homeless outreach specialist Jessie Angeles Jr. drives his work vehicle around areas in North Park where people without shelter typically gather, March 7, 2019.
Meet The Man Helping To Shelter Mid-City’s Homeless
A new homeless outreach coordinator serving City Heights and North Park is part of an experimental project to bring support to the area's homeless population. You can hear this story and other local news every morning by subscribing to San Diego Stories, KPBS’ daily news podcast. Subscribe via iTunes,Google Play or your favorite podcatcher.

Corrected: January 28, 2023 at 9:30 PM PST
Editor's Note: Price Philanthropies, which provides funding for the coordinator position, is also a supporter of KPBS.