People living in tents or RVs around Columbus Park were given two weeks to move.
Homeless advocate Shaunn Cartwright handed out water, fruit and hygiene kits throughout the day.
"This is what happens is you have a guy who's mentally ill, deeply, and he's sitting here trying to push his own van by himself when it's 95 degrees," Cartwright said.
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The city says because the encampment lies under the San Jose airport's flight path, they are required to keep the area clear of birds, trash or campfire smoke.
"This does nothing to help get any of those people housed, and it's not for any reason other than to make it look like you're doing something," Cartwright said.
Some people just moved their things across to the city-owned area.
Sandra Uecho lives at that encampment with her children and three grandchildren including 7-year-old Mila and one-month-old Liya.
"Estamos muy asustados," Uecho explained they're scared.
They moved from Columbia five months ago. It's difficult to find a job without a proper work permit. Having an option where the entire family can be temporarily housed together is what's she's hoping for.
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The city aims to have the area fully cleared by the end of the month.
Mayor Matt Mahan released a statement:
"Our fundamental responsibility is keeping people safe - that's our highest priority above anything else we work on, including ending homelessness. There are certain cases, where an encampment is so unsafe and violating so many laws, that we can't wait for our solutions to scale," said San Jose Mayor Matt Mahan. "The FAA requires us to keep certain areas around Columbus Park clear because it is in the airport's flight path. This is exactly why we're working with urgency to expand safe sleeping, safe parking and tiny homes so that we have adequate capacity to serve the people living in unsheltered, unsafe conditions along our streets and creeks. We simply don't have enough capacity today for the over 4,500 people living outdoors."
Similar efforts are underway in the East Bay.
The mayor of Antioch, Lamar Hernandez-Thorpe, had words for surrounding cities.
"I want to be very, very clear that Antioch is not going to be a dumpsite for the Bay Area's problems," Hernandez-Thorpe said.
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Mayor Hernandez-Thorpe is proposing to change the city's no camping ordinance to specifically include trails, waterways and city plazas - not just city parks.
He said the city applied for nearly $6 million from the state for 'encampment resolution funding' and he does not want that funding compromised.
"All you have to do is drive around and see the new RVs that are coming to Antioch, we all know where they're coming from, they're coming from other cities that are deliberately pushing people out," Hernandez-Thorpe said. "That's not fair for the guy who graduated from our local high school who has been waiting for services."