Comedian Jamie Kilstein has undergone quite the transformation over the past few years, from being surrounded by liberals who have abandoned him to realizing conservatives are much more "open-minded." So, he wasn't surprised by how quickly the rich leftist residents of Martha's Vineyard shipped out the illegal immigrants Gov. Ron DeSantis sent over. Jamie gives his take on that hypocrisy, as well as the why he believes "nuance shouldn't be edgy"...

Transcript

Below is a rush transcript that may contain errors

GLENN: Jamie, how are you, my man?

JAMIE: I laughed so hard, at that intro. Because it was like -- I felt the same way. I was like, oh, tragic. Tragic. Tragic. No, I'll be funny. Everything is fine. And you're like, back in the day, before my life imploded, you know, a comedian gets introed for a radio show. And, you know, you've heard this guy on Conan O'Brien, and now my intros are just this long, tragic tale. And my next guest is searching for redemption, from purgatory.

GLENN: Right. Right.

My next guest has been considering suicide, but today he's fine.
(laughter)

JAMIE: We caught him on an off day! He doesn't know how to tie a proper knot.

But, man, I'll tell you, you did say something. And you covered this on your podcast. But you did say something so wild. Which is, me being painted as this sort of outside thing to be examined, is so bizarre. Because like, new answer shouldn't be edgy. Having multiple opinions on different issues, shouldn't be controversial. And the fact that I feel like, the people -- and you've gotten this too. Who have gotten the most thrown under the bus now. And don't get me wrong. I used to be that way. Pick a side. And started losing friends like the rest of us. But now, I think it's so healthy. And I also think it is representative of the majority of people. But the majority of people, are too nervous, to anger their own tribe stop if they do -- you know, if it's a conservative, who is like, I don't really care about gay marriage. Or if it's a liberal, who is like, yo. These drag shows are like, not okay. They're afraid to sort of get ostracized from their own group. Because, you know, things are so rough retain. We're clinging on any sort of life support. That we just keep it quiet. So I think the majority of people are going to start speaking up, like, hey, man, there's crazies on both sides, and there are also really cool people on both sides.

GLENN: So if your life hadn't exploded or imploded, do you think you would have come to this, or did it take a shipwreck to get you there?

RUSS: I think about this a lot. I think about this a lot. I do really think it has taken some sort of shipwreck.

GLENN: Yeah. I have to tell you, I think -- you know, I've said this all the time. You know, I'll be at church. And they'll be like, oh, share your testimony. And I'll be like, yeah. I really feel sorry for you guys. That you didn't have a life that imploded. Because I really needed redemption. You know what I mean?

I really needed -- and I don't know if I would have actually found it, if it wasn't -- you know, if I wasn't on a ledge.

JAMIE: Yeah. And I'll tell you, I -- you know, I -- I know I'm supposed to be funny. But I think this is important.

GLENN: No. Just be you. Go ahead.

JAMIE: Yeah. I think -- I think that it was -- and not to, you know, kiss up. When on a radio conservative show, people always tweet me pictures of red pills. Like, I know. I know. It's happening. But I will say, I did not feel that way for ten years. Because for ten years, I was only still surrounded with liberals.

And, you know, I'll -- I'll show many of them off-air, off any -- I would love to have you on my podcast. Like, I don't want to get in trouble. For the record, I don't think what you did was bad. And, you know, I cheated on my girlfriend in my 30s.

And my wife is furious. She thinks what happened to you wasn't bad at all. Anyway, we can't be seen together in public, and if you could lose this number.

And then I started, when I moved to Austin, Texas, which is I think legally required for white podcasters. When I moved down here, I suddenly -- I was hanging out with conservatives and moderates and Libertarians.

And people who, they didn't have to go check Twitter to see if they could be your friend.

People who just sincerely saw you for who you are.

How do you treat my family? How do you treat my kids? How do you treat me?

And these are people from Jiu-Jitsu. You know, all over the place. And not necessarily from the political sphere. And that's when -- I mean, we're talking this year at 40. You know, I had an affair ten years ago, eight, ten years ago. We're talking this year at 40 years old is the first time. Meeting you, it's the first time, that I've been like, oh, what happened to me was a blessing. What happened to me did lead me to find God. It did leave me to open my mind. It did lead me to changing my views on certain things. But, dude, when it felt like nobody had your back, it was just me -- and I've had people tell me.

You know, I had a great comedian. Brendan Fraser, I did his podcast a long time ago. And I was still living in LA. And he was like, bro. This is going to be a blessing. You get to restart. And I was just like, shut up. Like, my life is awful. Like, I live -- my apartment in LA, after my divorce was so bad. You know how hard it is to break a lease, especially like in LA and New York. It was so bad, that when I couldn't afford it anymore, and I went up to the landlord to be like, hey. I have to break the lease. He literally looked me in the eyes and goes, just don't tell anyone what you saw here. And I was like, oh. Okay. Like, that's out of a horror movie. It's out of a horror movie.

So then I was like, no. Dude. I don't see how things are good.

And now that I've been around -- and I never thought I would say this -- the more open-minded people. I thought liberals were the open-minded people, because we listen to Kendrick Lamar. But, like, no. The conservatives I've hung out with are more open-minded. And, again, it's funny. Because I used to make fun of religion too. It's like, no. They're the ones that talk about forgiveness. I thought liberals were the ones that talk about forgiveness. Because of prison reform. I thought we were open-minded. But the ones who absolutely practice what we preach. Who I've met. And there are plenty of liberals who are cool.

GLENN: And there are plenty of conservatives, that they suck.

JAMIE: That's the total opposite, and that will be monsters. So it's fine.

GLENN: Right. Right. Right. Right.

So let's talk a little about Ron DeSantis. Ron DeSantis. And how did you view this? And what did you -- what did you learn?

JAMIE: Put your lab coat, buddy. I went all over the place with this. I went so schizophrenic with this. Because when it first happened. I was like, stupid, liberals.

I thought it was so funny. Because I've hung out with rich liberals. Like, there's part of me, that I'm surprised the Martha's Vineyard didn't have the immigrants like, sentenced to death.

I hung out with people, who will tweet about Black Lives Matter, but will cross the street when they see a real life black person. I've been to vegan Hollywood parties, that are just missing a whites only sign.

And separate water fountains. I've been around these people. And so, seeing them have to confront their own hypocrisy was good.

And just to the liberals, by the way, and to attack the media. The media just wants us to see the worst cases.

You know, there were people who took residence, and who fed them, who cooked them meals, and we've never seen that stuff. You know, the media --

GLENN: Yeah. But I'll bet you, it wasn't the people who had the big houses. I'll bet you it was the average person that was there year-round, and those aren't rich people.

JAMIE: No. I bet you, you're 1,000 percent right, 1,000 percent.

Yeah, that's always the funniest thing. When you see Black Lives Matter, or the little lawn sign, in between like eight layers of armed security.

Where it's -- it's performative, right? And so I thought that, you know, I was like, good. But then, I don't know if you had this moment. Where you are on DeSantis.

Oh. And I also will say, I do love this sort of no nonsense exit. Where it's just like -- where we sent a bunch of people -- it's the Texas attitude. And I feel like Florida is like the Texas of the sea.

But then there was this moment -- there was this moment, where I was like, ha, ha, and I was looking at my conservative friends on Twitter, and they were making jokes about it. And it was really funny. And then, again, I don't know if you guys had this. But I was like, where did he get those brown people from? I had this moment of like, wait a second. Did Ron DeSantis like, did he kidnap a bunch of immigrants? Did he traffic them? Was he holding them in his basement?

I had no idea, where -- and that, by the way, that's the most Florida man thing you can do is just kidnap a bunch of immigrants.

The only thing that would have made that more Florida, is if you would have had an alligator guarding them. Bro, just hire actors. Just hire Mexican actors.

They're in right now, cast Latino-esque, or whatever they're called. But don't take real starving, desperate people and trick them, just to own the libs.

Like, I would have rather Ron DeSantis like put on a festive Mexican costume and the little fake mustache, and just gone to Martha's Vineyard himself.

Like, it would have been great. But that was one of those moments, where like, I couldn't let myself fully get wrapped up in --

GLENN: But wait a minute. Wait a minute. He didn't. And everybody signed a release form. They knew where he was going. Come on, man. You wouldn't -- I will -- I'll claim to be an illegal, if you'll -- if he'll send me some tickets to go to Martha's Vineyard.
(laughter)

JAMIE: Yeah, but then you do ask yourself questions, right? Where you go -- like, what I had to do was take myself out of it. And go -- and think about being.

I mean, it's the crazy thing, right? Where you just go, okay. What's it like to be those people?

And I think we're so used to looking at the news through the lens of social media. Where it seems like a video game. And as a video game. That's hilarious. And round one. And the liberals look ridiculous. And I will give Ron DeSantis credit as well. Which is, this is what it took. The media. This is how far we have to go, to get the media to cover this crisis.

GLENN: Yes.

JAMIE: And I was also really surprised -- because I said them, where I was like, hey, did Ron DeSantis just kidnap a bunch of Mexicans or whatever? Venezuelans, whatever? And a lot of conservatives, who I thought were essentially just build a wall. Not my problem. I don't want to see that. Were actually giving me very heartfelt responses. Where it's like, no. Dude. Of course, we don't want to see immigrants families starving. It's just the system has been so broken, that this is what happens, right?

They see that both sides.

GLENN: I have to tell you, when the response from the left and the media has been so telling. They -- they keep saying, all these cities keep saying, they're sanctuary cities. We don't have room.

Wait. You have -- New York, you think a little teeny town of 20,000 people can handle 25,000 people that just came across the border? And you don't even talk about it. You don't talk about the fentanyl. You don't talk about the actual smuggling of humans. The rape that is happening from these drug cartels, as they're bringing people over. It's a horror show. And they don't care.

JAMIE: Yeah. I'm so glad you said that, because this reminds me.

Because I was thinking of when you said New York, I started thinking about LA. And there was part of me that was like, God, LA can just build houses for TikTok influencers. Like, why don't we help real people, right?

But I remember the last time I went to LA, which was just a couple of weeks ago.

It was bad. I mean, the homeless problem was just as bad, if not worse, than you do see on social media.

And I have this like, heartbreaking moment. Because, again, as we look at stereotypes of the left, and the right.

You have liberals saying, hey, man. Don't worry about it. Likable, you know, let them build a tent. Let them -- and they're doing it under the guise of, we would be compassionate. And then you have conservatives, which I've seen. Who just go, ew, gross. Look at this. Look at what a disgusting mess this city has become. Blah, blah, blah. And what's not happening in the middle is legit compassion, where when you walk by these people, seeing them as people. Asking yourself, how we got here. And then looking for a solution, right? So you have politicians like -- I think it's Michael Shellenberger, who tried to dethrone Newsom.

GLENN: Yeah, yeah, he's great.

JAMIE: He's great. And he was a big liberal. And all my friends on the left, hated this guy. So when I researched him, I thought he was just going to be like, march the homeless in the ocean.
(laughter)
And I started like reading what he's trying to do, and it's like, no. This guy is actually willing to be hated. And is trying to say, don't put them in tents. Don't put them in hotels. It literally doesn't work. You believe in science? It doesn't work. We have to get them into treatment. We have to help them.

And very similar to what you were saying, about immigration. Where it's just like, I feel like the left is so good at pretending to care, right?

And pretending to be compassionate. But it's like, man, if what we're doing isn't working.

GLENN: Right.

JAMIE: And, in fact, making it worse. We have to look at the other side.