Ms. Breed was joined by about 30 city workers, including her aides and security detail, public health officials and eight police officers. Their numbers dwarfed the four homeless people who were staying put on the sidewalk.

Joel Beiswanger, 49, sat amid a pile of his belongings as the police officers stood nearby and watched him. Wearing a bright orange sweatshirt and pajama pants emblazoned with Santa Claus, he said he found shelters too stressful and had nowhere else to go. He said he has been homeless on and off since he was 14.

Mr. Beiswanger took issue with Ms. Breed’s statement last week that she wanted to make it “uncomfortable” for people to live on the street.

“Where are the bathrooms at? Showers? Where is there comfort?” he asked. “Every week, someone comes through and takes everything you own, no questions asked. I guess it’s how you get your votes.”

Emmanuel Siple, 48, woke up from a nap in a tent nearby. He said a drug and alcohol problem and divorce had led him to live on the streets, and he resented being “micromanaged” by city workers. The threat of jail won’t convince him to stay in a shelter, which already feels like jail, he said.

Ms. Breed did not engage with the homeless men, observing them from across an intersection. She said she did not want to be recorded by a group of activists for homeless rights who had shown up to monitor the clearing and take videos of the workers.