Andy Robledo added “Orange Tent Guy” to the job list on his LinkedIn profile last November. He earned the nickname when he supplied roughly 250 unhoused Chicagoans with orange ice-fishing tents to help them survive the cold.

Robledo said that within a week of installation city officials threatened to remove some of the tents from under viaducts and in alleyways. He said a standoff ensued, and the city backed down afterward and vowed to collaborate. A Department of Family and Support Services statement said they are not affiliated with Robledo, but met with him “several months ago” to discuss street outreach and cleaning protocols.

Since last fall, Robledo has been fundraising to purchase new tents. Each tent costs roughly $500 to buy, install and heat. He will host a pop-up market this Saturday at Marz Brewing on the city’s South Side to raise money for the 250 tents he aims to put up this winter. The event, from noon to 6 p.m., will feature music and vendors selling a wide array of items.

Sporting a tie-dye shirt and pink Crocs in his plant-filled Pilsen apartment, Robeldo said he’s already counting down the days until the temperature outside drops.

“In less than 150 days, I think there’s going to be a lot of people left outside,” Robledo said, “and I think we’ll need to build a lot of tents.”

He knows the number of tents needed is far from what he can supply.

City data show more than 6,100 people were experiencing homelessness as of this January. That’s compared to roughly 3,900 individuals who were unhoused in 2022, though some critics say this number is a vast undercount. And the city’s shelter system is struggling to meet demand amid two converging crises: homelessness and an influx of asylum-seekers.

Robledo is hopeful about the new mayor and his support for “Bring Chicago Home” — a plan to increase the real estate transfer tax to fund homelessness prevention.

In the meantime, Robledo said he will keep giving out tents and food to people on the streets. Not everyone is on board with that idea, he said.

Robledo said his work has drawn criticism from people who say advocates like him should focus on getting people housed instead of giving them the means to survive on the street. But he has also received support from other organizations that share in his mission.

Farhan Ahmed of CHI-Care, which feeds hundreds of unhoused people across Chicago each week, is one of several nonprofits donating meals to the people Robeldo helps.

Ahmed said his support for Robledo’s cause stems from their shared belief that everyone should have access to food, water and shelter.

“Most unhoused people, they’ve been kind of orphanized,” Ahmed said. “There’s no one really there to help pick them up. So we should just try to do the best that we can instead of criticizing people who are helping.”

Ahmen said it can be hard for people to empathize with the unhoused if they’re never seen what it’s like to live on the streets up close.

For Robledo, his own struggles led him to his volunteer work. He overcame alcoholism four years ago, he said, after he quit his corporate job in pursuit of “something more.”

He then started delivering plants in a pickup truck. When the pandemic struck, Robledo watched from the driver’s seat of his car the long lines of people that stretched outside food pantries.

“I could have been out there just like a lot of the unhoused folks that I’ve helped get sober, get into housing or have built tents for,” Robledo said.

Today, he uses profits from his plant delivery business to buy meals for the unhoused. And since then, he’s put names to the faces from those queues.

It’s them he said he can’t turn his back on as winter approaches.

“If we wait until the weather’s bad to start caring about this … It’ll be too late.”

Anna Savchenko is a reporter for WBEZ. You can reach her at @annasavchenkoo.