Now in his second season doing The Problem With Jon Stewart podcast that also has a video component on Apple TV+, the comedian just had SF Mayor London Breed come on for an extended conversation on what he calls San Francisco's "complicated soup of problems."

We all know that Breed prefers the word "challenges" to "problems" when it comes to talking about things like homelessness, Tenderloin drug dealing, and the city's struggling downtown. But Jon Stewart isn't one to mince words or fall back on euphemism, and it's somewhat refreshing to hear the mayor in conversation with someone as intelligent, compassionate and no-bullshit as Stewart.

He begins the podcast by acknowledging that San Francisco has been a symbolic punching bag for conservatives for decades. "I don't know if it's Sodom and Gomorrah, but certainly it's one of them," Stewart says.

And he says, for conservatives and people who are just generally intellectually lazy, "San Francisco" has just been shorthand for talking about a slew of societal problems that are hardly confined to just cities, let alone liberal cities.

"Rural areas, city areas, they are all facing these devastating, complex issues, and it's super easy to point to the liberal bastions that are confronting them," Stewart says. "But red states take fentanyl, too, baby. Red states have property crime. Red states have homicides, sometimes at much higher levels."

The conversation Stewart has with Breed is an extension of last week's episode in which he focused on incarceration in the U.S., and he discusses with the mayor how she's been criticized both for being "too tough on crime and too lenient on crime."

Breed talks about her focus on the Tenderloin, saying that she had been advised in the past not to "touch it" politically, because "once you touch it, you own it," and it's "always been that way" and is unlikely to change. (Stewart also says, "I was there in the 80s. It's always been like that.")

"For me, many of the people who live [in the Tenderloin] are people I grew up with," Breed says. "Many of the people who live there are formerly incarcerated, have substance use disorder challenges, immigrant families and business owners, and seniors — this is a community of people who live in poverty in many instances and are neglected. Why should they have to live in the kinds of conditions where the streets are not clean, where there's open-air drug-dealing, where there's violence consistently?"

Breed mentioned that she had pushback for wanting to crack down on fentanyl dealing and Stewart asks, "Who is arguing against arresting fentanyl dealers?" And Breed gets a chance to throw some familiar shade on the Board of Supervisors.

"There are members of [the Board of Supervisors] who feel that they are the carrier of the torch for progressive values in San Francisco... and to be clear, these are people who don't know what it feels like to live in these conditions. And they are constantly pushing against the recommendations that are even being made by the people living in those conditions," Breed says.

Stewart and Breed get into a conversation about solutions, and Breed says that conservatorship for the severely mentally ill is another tool — and one that needs to be available even though some argue about infringing on people's liberty.

"All of a sudden, people are, like, 'Wait a minute. Conservatorship? Look at what happened with Britney Spears. We don't want to take away someone's rights," Breed says. But she goes on to cite an example of an elderly woman, presumably familiar to authorities, who "walks around naked dragging a blanket" and gets violent when anyone tries to approach her. "The only thing we have to do is detain her, put her on a 72-hour hold, she goes through the process, 'I'm okay, I can take care of myself,' and that's it, and that is not a solution. That is doing the same thing over and over and expecting to get a different result."

When it comes to drugs, Breed discusses her desire to "make it normal for people to get treatment" and "make it normal to have safe-consumptions sites, so that people struggling with addiction can not do it in isolation... and when they're ready for treatment they can get the help they need... People are always going to be addicted to something, so how do we create a better system?"

Stewart asks, "Do you feel like you're just spitting in the wind?... Does any city, not just San Francisco, but does any city have the kind of resources, and the kind of will, to tackle this enormous mental health crisis, and this enormous substance abuse crisis, which is fueled by so many other things in a city — is that a realistic goal? Or is the goal just to stop the bleeding?"

"I think what we are trying to do in San Francisco, sadly, is just trying to stop the bleeding," Breed says. "We can't do this alone. We can't arrest our way out of this problem... we need help from the state and federal government."

They then get into talking about diverting resources from building prisons to building more mental health facilities and adding in-patient beds in cities where we need them most.

Listen to the whole podcast on the Apple Podcasts app, or online here.