The Clintons had recently purchased their home in Chappaqua, but they hadn’t moved into it yet. After an inane discussion about Hillary Clinton’s choice in home decor and lack of a New York driver’s license, Matthews began to offer his thoughts about a statement she had made concerning New York City homelessness policy. A taped statement by Clinton began his next segment. Mitchell snarked along with her host after that:

CLINTON (videotape): No violent or dangerous person should be on our streets threatening themselves or our community. But we don't help matters by throwing them out of shelters onto the street or putting them into a revolving door jail time where they go in and out and are on the streets again. The goal should be treating such people and, where necessary, putting them into situations where they can be treated effectively.

MATTHEWS: Boy, you've got a tough job being an objective reporter in a race like this. I don't even have to try. Here's a woman complaining about homelessness and how they're being treated when she hasn't even checked into her shelter yet!

MITCHELL: She's a—

MATTHEWS: This woman doesn't even have a home in New York!

MITCHELL: She empathized; she's a homeless person.

MATTHEWS: Right!

Ha ha ha ha ha ha ha! Clinton was talking about the homeless—and she didn’t even have a home yet! And then, things went from bad to worse. Jack Welch’s favorite fruitcake decided to say a few weird things about his own interactions with the homeless:

MATTHEWS: Let's talk about the homeless, because the homeless—most of us men, maybe more than women, because guys reach into their pockets for change—women have to go in their pocketbook. I really think it's easier for a male to give a half a buck or a quarter to somebody on the way by because of guilt or—

MITCHELL: We still manage to give.

MATTHEWS: I know, but you could stop—and also guys, I don't know what it—

MITCHELL: And we're guiltier than you guys are.

MATTHEWS: I don't think that's true. I'm—I always feel like saying I give—in San Francisco, it's a big problem there; you give a guy a half dollar or whatever you have available or a quarter or a dollar even sometimes, if they really look in trouble, and then you feel like the next guy you get to, he doesn't have a—you had—like you had—you put a, you need to put a badge on, “I just gave at the last corner here.” HA! But you get hit with the same kind of ferocity, the same kind of—sometimes pathetic, sometimes intimidating manner. And I think people who pay taxes and, and give to church or synagogue or something, say, “Wait a minute, I do a decent job here,” and if a person comes up with a particular case, I'm gonna be open to him. But if they're just here to intimidate me—you know, that's what it's about.

MITCHELL: Well, that—that's exactly why Rudy Giuliani has sort of the right tempo of New Yorkers. He really gets that.