Dave Portnoy on Trump, the manosphere, and his advice for Democrats

Steve Inskeep: Dave Portnoy has opinions about Donald Trump and bros. Somebody who maybe likes sports and wants to get laid, which I don't think is a bad thing. How does the founder of Barstool Sports think about voters like him? I'm Steve Inskeep on a special edition of Up First from NPR News. Dave Portnoy doesn't always get along with the media.

Dave Portnoy: They asked me for a quote about something the other day. I said I'd rather put a pencil in my eye than speak to you guys.

Steve Inskeep: But he talked with us about voters known as barstool conservatives. What keeps Portnoy on the president's side even after Trump tanked the stock market?

Dave Portnoy: I was mad, but I told myself, I was like, he said he was going to do tariffs.

Steve Inskeep: Also, what if anything could get more men to vote for Democrats? Stay with us for an extended conversation with Dave Portnoy. Barstool Sports has been around just over 20 years. It features podcasts, web stories, lots of ads for gambling. Lots. And also Dave Portnoy talking about things like watching basketball star Caitlin Clark.

Dave Portnoy: Because I was there for it. I was decked out. Fever hat, fever sweatshirt.

Steve Inskeep: Oh, yeah. Yeah, I saw that. His business model is to cover whatever guys might talk about while at a bar watching sports. This now includes politics, which he riffs about on social media.

Dave Portnoy: The thing about me is when I see something and I get an opinion and it bubbles up, if I don't get it out, I just combust. I just, like, I may just explode.

Steve Inskeep: When progressives denounce his language about race or women, as they often do, he says that's why men voted for President Trump.

Dave Portnoy: Maybe they don't trust the extreme left like you, who seemingly hate all normal white guys.

Steve Inskeep: He also criticized Trump when Trump's tariffs tanked the stock market.

Dave Portnoy: I went super viral when I said I lost $7 million. I'd kill to be back to losing $7 million.

Steve Inskeep: To be clear, he's still with Trump. But when we met face-to-face, we also heard some surprising nuances. One of Portnoy's homes is in Miami, and we met near there in a podcast studio. Let's just hear him in his own words. Welcome.

Dave Portnoy: Thank you. Thanks for having me.

Steve Inskeep: If people don't know, I want to know a little bit about your background. You're from Boston.

Dave Portnoy: Correct.

Steve Inskeep: Your parents were a lawyer and a teacher.

Dave Portnoy: School teacher, yep.

Steve Inskeep: Which I like because my mom was also a teacher and my dad too. And I read that you went to the University of Michigan and got a degree in education.

Dave Portnoy: Correct.

Steve Inskeep: Were you planning to be a teacher?

Dave Portnoy: No, I don't think I was. So at Michigan, to graduate, you need to pass your language requirement, which I just could not do. So I was through Spanish 3 in high school, got dropped back down to remedial Spanish when I took the test, couldn't pass it, just couldn't pass it. I realized if I transferred to the educational school, there was no language requirement. So that was my fast pass to get my graduation degree.

Steve Inskeep: So you were just trying to escape.

Dave Portnoy: I was just trying to graduate with a degree, yeah.

Steve Inskeep: But you had a vision of something else you were going to do in life.

Dave Portnoy: Yeah, I mean, there was a time when I thought maybe gym teacher was like something. I knew I wanted to enjoy my life, so I was a sports guy. But I was really, at that point, let me get the degree and get out of college.

Steve Inskeep: And you ended up developing your own business, which is a long and amazing story. But you started in, I mean, before the internet was as big as it is now. It was a physical newspaper at one time. Is this right?

Dave Portnoy: Barstool Sports was basically a four-page gambling rag, like fantasy sports, that type of thing. And I would hand it out outside of subway stations in Boston, literally up 4 a.m., screaming at people to take the newspaper. I'd do all the jobs in the paper. I'd write, sales, whatever. And then I'd go back to the subway station around 4 p.m., hit people on their evening commute. And that's how it started, and that's how it was for the beginning years.

Steve Inskeep: Did you have a vision for what it was going to be?

Dave Portnoy: No vision. I just really want to wake up and enjoy what I did. I was interested in the gambling industry. That was something that interested me. So fantasy, sports, that type of thing. I never dreamed it would be what it was today. If I could have squeezed out 60 grand a year, waking up happy, working for myself, that would have been a win.

Steve Inskeep: It seems to me you then caught a couple of big waves. And one is the internet getting bigger and bigger. And the other is gambling and sports getting closer and closer, more intertwined. Is that how you see it?

Dave Portnoy: I caught a lot of waves. I want you to say, too, right time, right place, right guy throughout the years. But without the internet, I'm not here with Barstool, and Barstool isn't here. Found the right writers, right people to work. The gambling part of it, we actually sort of went away for a while. But I would say what elevated my bank account for sure was the changing of the law in the United States, where you could now legally bet on sports. We had started as a gambling newspaper. And then, I don't know, 10 years, I'm guessing, when that law changed, we were uniquely positioned with our audience for all these companies. It was a land rush. I mean, it was a goldmine of people throwing money at advertisers, different type things. So we were just right time, right place again for that.

Steve Inskeep: So I think about where your business is now. And I mean, you're at some intersection of sports, of gambling, of culture, a little bit of politics, a little bit of news. But what's the one-sentence description? What essentially is it that you're doing?

Dave Portnoy: It started, and I think it rings true for the most part. Barstool sports was supposed to mean anything guys would talk about sitting down at a bar watching sports. So that's pretty wide open on what it could be. The only caveat I'd say, which I didn't anticipate, we have a big female audience too and launch some of the biggest female podcasts and podcast stars. So it's really what a guy or girl may talk about in their living room or for guys in a locker room or girls in a locker room. That's really, it's supposed to be plain speak, basically, busting each other's balls and having fun.

Steve Inskeep: Does the, with those podcasts, does the audience segregate or self-segregate? Men and women listening to different things?

Dave Portnoy: It generally does, but it depends on the podcast. It depends what they're doing. I worked on a podcast until recently called BFF. And this was basically, I thought at the time, Barstool was starting to get old. And TikTok was developed. And if you went to people on TikTok and said, what's Barstool Sports? They've been like, we have no idea. So I knew I had to penetrate that audience. So we teamed up with a TikTok star, Josh Richards. Basically, think of a boy band except for TikTok. That's really what it is. And Barstool got big in TikTok. Now, that audience, male, female, everybody are talking about things for multiple people. Then we have Spitting Chicklets is a hockey podcast. That'll be very male-centered. Call Her Daddy, which is, I still think to date, the biggest female podcast of all time, that was really female-focused. So it's just what are they talking about?

Steve Inskeep: I follow on Instagram your pizza ratings, your political commentaries. The same things are on TikTok and every other platform.

Dave Portnoy: Correct.

Steve Inskeep: Are you in real life the same person that I see on Instagram?

Dave Portnoy: Yeah, it varies on what you're doing. It may be an amped up, a WWE version of it at times. And I have a vehicle obviously to get my thoughts out with it, but it's me for the most part. I mean, again, it depends the situation. I got arrested protesting Tom Brady and Deflategate. We went myself, three other Patriot fans who worked, handcuffed ourselves to each other outside of the commissioner's office and said, we want to talk to Goodell. I thought what they did to Brady was wrong, unfair, all of that. If I had a nine to five, am I going and handcuffing myself to, uh, in front of the headquarters? No, I'm not like, I'm not a crazy person, but we are in an entertainment business. So that worked for us.

Steve Inskeep: You wanted to make that point. You also wanted to get attention for making that point.

Dave Portnoy: Yeah. And even in that, we, one thing I will say about us, and I've said about that, and we do it for our readers, our fans. Sometimes I don't think about the effect beyond who I'm speaking with. And I think that sometimes surprises me, sometimes doesn't. But like our crowd knows me. So we've been around 20 plus years. So they can almost predict what I'm going to say before I say it. But a lot of times I'll see people who maybe less and less who don't know who I am. And like, holy cow, what's this guy saying? And they don't have the context or anything of who we are and where we came from.

Steve Inskeep: Who in your mind is your audience? The person you're talking to when you're talking.

Dave Portnoy: I'd say a very, I'd say like 90% of like normal Americans. Like I think the extreme left and the extreme right are like a little bit nuts. But this for the most part is people trying to grind through their day. They have a normal job. They're in college, whatever. They're trying not to take things too seriously and enjoy their lives and maybe have an escape for a couple minutes, hours, however they consume us. But really that's who I think our audience is.

Steve Inskeep: There's this phrase that people use I don't know if you like it or not. The manosphere. Talking about male podcasters and internet stars talking to bros about bro things. Do you accept that there is such a thing and are you part of it?

Dave Portnoy: I think there maybe is. But I've seen myself lumped in all sorts of different manospheres. I've seen barstool Republicans. I've seen stuff that I would say are inaccurate how they describe us. There's always bros. I mean, I think when you say the word bro, it's somebody who, you know, maybe likes sports and wants to get laid, which I don't think is a bad thing at all. I think that can sometimes be like shamed recently since I've been doing barstool for sure. And I think the bros don't like being shamed for that. But I think it's a far more complicated word than just to be like, you know, the revenge of the nerd type guy in the football locker room who's like nerds. Like no, I there's certainly male focused publications and again I guess you could say we're one. That's what people say probably because they think of me. But then if you actually look at who we employ, we have just as much of the equal female stuff going on. So you know, bro, what they thinking? Rogan, they're thinking Theo Vaughn. I get thrown in that a lot.

Steve Inskeep: Do you accept it? Are you in that group?

Dave Portnoy: We have a male audience. Like we may feel very differently on certain issues. So I think if somebody says bro, what are they saying? You love Trump. I voted for Trump. It's more an indictment of I would say the Democrats, an endorsement of Trump politics. I think people would say that is not a typical bro standpoint. So I think there certain things. I think they think you, I would say I not. And I don't know that like Rogan is. I think there's intricacies within each person. It's hard to just say well that fan base or that person is all these rules.

Steve Inskeep: Do you think that?

Dave Portnoy: I think it's blunt talk is mostly just saying I think it's being the bottom line blunt and more not politically correct. Like not caring necessarily what that is. If you want to say that's bro, I'm definitely that. I don't care what people think about me. But I guess I just don't think it's as straightforward as what I perceive when people mention me.

Steve Inskeep: Has something happened in society that has made men like that more political than maybe they would have been 10 years ago?

Dave Portnoy: I would say I had no plans. If you told me we'd be on NPR and in a political leaning podcast like five years ago, I'd be like you're crazy. It's something I have no interest in. I've actually always with Barstool prescribed to the Michael Jordan like red states buy sneakers and so do blue states. So we're not in politics. You're in business. In politics, you're gonna piss half the people off no matter what you say. So that's a potential customer. Why don't you want them? So I didn't think I'd be here. But during Barstool it became increasingly obvious that you couldn't tell jokes and you couldn't do things that I don't think you should be ashamed for. And I felt like that was becoming prevalent. Maybe it's because of Barstool where we consider ourselves a comedy brand and would come under fire for things. So not, and it was on schools, it was in the media. And really, I felt that that was a something that drove me to probably be a little bit more political.

Steve Inskeep: One of your posts in recent weeks, you talk about your feeling that the political left makes, I believe the phrase was normal white guys feel like you're evil or bad or something like that.

Dave Portnoy: Yeah.

Steve Inskeep: I'd stand by that.

Dave Portnoy: At this point in our conversation, Dave Portnoy took a breath. Some listeners get a break now and then we will hear why Portnoy says he stands by that.

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Steve Inskeep: So he asked Dave Portnoy about a social media post in which he said he felt the left was out to get normal white guys like him. Here's what he said.

Dave Portnoy: I'd stand by that. And there's an element to me that I felt if you're, and now this is somebody, I started a business from scratch and really didn't get any help, moved home, worked, didn't take a vacation day for 10 years and grinded my ass off to get where it is. And I felt that there was, I should somehow have shame as being a white person who wants to make a lot of money and live a great life. And that bothered me. And there's different things that happened along the way that really reinforced it. Like, I know you had AOC on. She jumped into my world. I didn't really even know who she was, but we had a rival website way back in the day, Deadspin. Hate them. They went from being the most off-the-cuff, non-PC website to doing 180. They deleted all their history, and suddenly, you couldn't say a joke. They apologized for all of it. Anyways, they were going out of business, and they had a union and we do not have a union and I just hate Deadspin. So I did something like, hey, the union couldn't stop these guys from losing all their jobs and we pay well and do great. AOC jumped into the fray and tweeted at us, it's like illegal for us not to have unions and threaten unions. Our reaction to that was we created a fake union within Barstool and we were actually playing it like they were fake calling to leak like, you'll never believe what Dave is doing and all this stuff. This turned to a big thing. I had to apologize to the National Labor Relations Board.

Steve Inskeep: Huh.

Dave Portnoy: Things like that drive me nuts. Anybody who objectively looked at what we're doing, new bar so it's like these guys are joking around. You had to apologize. Why? Because we threatened our employees. I tweeted out as part of the ongoing satire of what we do, anybody who creates a union I will bust that union to shreds and you'll be gone. And it continued like she'd say she'd throw bar back and weed up the ante and it was our own people with a union we had created as kind of like a Saturday Night Live skit creating all the issues.

Steve Inskeep: So do you think you ought to have a real union?

Dave Portnoy: No, no. We definitely shouldn't have a union. You know what our union is? Talent. Like if we've made, so if I look at the people who've come and gone just briefly, like Alex Cooper left Barstool, made 70 million from Spotify. I think McAfee got about 100 million at ESPN. Bussin' with the Boys, the podcast just got 60 million from FanDuel. Also, I don't fire people. We pay great and if you're great, we use a model like, I look at us like an athletic team, right? If you are a great player and we sign you a two-year contract, at the end, you'll have the option. You can go get more money because we can't pay you. You stay with us and we pay you. But talent for us, we're in a talent business. So talent pays. There's no, we pay well, we do well. If you look at the history of our company, almost nobody leaves. We don't fire everybody. So we absolutely do not have a union. But I find it interesting, all the companies kill us for that debacle. They all have unions and their people all have been laid off and gone out of business. We haven't. We're thriving and have been for 20 years and people love working for Barstool.

Steve Inskeep: So there's this phrase, Barstool conservatism.

Dave Portnoy: Yes.

Steve Inskeep: Which you've heard. I looked up the definition of it on Wikipedia. I'll read you some of the words they have. Barstool conservatism. Pro-Trump, libertarian, no lockdowns, a COVID reference, no abortion bans, unwilling to accept liberal social norms, embraces sexual libertinism, anti-authoritarian, and lots of f-bombs. That's their definition.

Dave Portnoy: Yeah. I think I think most of those I agree with. So I guess a question for that would be, are they talking about me? Are they talking about Barstool? Because if you look at any media organization, unless you're talking about something that's political, we have people all over the place. We have people on the far left, we people on the far right. I mean, we have a gay podcast, we have straight podcast, we have sports podcast, girl. So we're all over the place. So I don't know that it's fair to judge the whole company based on what you think the views of me are.

Steve Inskeep: Is that a good summary of your views?

Dave Portnoy: I think for the most part it is. I think for the most part it is.

Steve Inskeep: You haven't done any f-bombs in this interview by the way.

Dave Portnoy: No, because NPR.

Steve Inskeep: Can I do enough? You can do it. You could, we could bleep if you, you should express yourself the way you.

Dave Portnoy: I feel like I'm speaking freely, but if it comes to the top of my mind, I'll let it rip. It's available.

Steve Inskeep: It's available. Let me ask another question now. Having voted for him, has Trump met your expectations so far?

Dave Portnoy: I think he has. I think Trump, for the most part, has done exactly what he said he was going to do. Now, people are getting upset at him trying to do what he said he was going to do. But he has, in my mind, done what he said he was going to do. Like, I had a rant about tariffs.

Steve Inskeep: Yeah.

Dave Portnoy: Right? Because I'm in the stock market and I do a show. You lost a lot of money.

Steve Inskeep: Yeah, I lost a lot of money.

Dave Portnoy: And so I'm going to rant about that. And he had a quote later that it wasn't his stock market. I think it was Biden's. Well, that's garbage. It's yours. Your direct statements are causing it to go up and down. It's bounced back. But I was mad, but I told myself, I was like, he said he was going to do tariffs. That wasn't like he was hiding that and pulled it out. So for the most part, I feel like he's trying to do exactly what he ran on and what he got voted for.

Steve Inskeep: What do you think about the way he's doing tariffs? I mean up down constantly up and down.

Dave Portnoy: Yeah, so that mess the stock market for sure. As he said, I think someone asked him the other day, he'd say it's a negotiation. And I think it's too early to tell where it lands and how it goes. And I think I said that one of my rants it was cut off because people clip everything, but it's like we'll see how it plays out. The stock market goes up and down. You can't kill the stock market. You can't kill the economy with this tariff scheme. But I think Trump would say I'm the greatest negotiator the world has ever seen.

Steve Inskeep: Do you suspect or assume as I think a lot of people do that somebody on the inside may be making money as he keeps saying things that make the market go up go down?

Dave Portnoy: I always think people are making money on the inside, so yeah. I'm sure people are making money.

Steve Inskeep: Does that bother you?

Dave Portnoy: It does bother me. But back to AOC, I agree with her that politicians shouldn't be able to trade stocks period. That that's crazy to me. But I don't think it's unique. In a weird way, like the Trump meme coin, that's so blatant in your face. I'd almost rather have that than like Hunter Biden doing some back deal that I don't know about. So none of it to me is good. But it's more straightforward to just have a dinner and everybody who's paying me should come to dinner.

Steve Inskeep: Yeah.

Dave Portnoy: Yeah. Which is what Trump did with the coin.

Steve Inskeep: With the coin.

Dave Portnoy: Yeah. So again, I don't like it and they are I sure making money, but this isn't. I wouldn't sit here and say well damn, like Donald Trump the first president ever to be making money. Like I think they all do. I don't trust any of them.

Steve Inskeep: There probably a lot of your readers that invested in that meme coin and have lost as it gone up and down.

Dave Portnoy: Well, yeah, meme coins is a crazy world. I actually made money on that one. But meme coins to me, and it's a whole different discussion. That is, you can't cry if you lose money in a meme coin. That's if you went to Las Vegas and put a dollar in a slot machine, pulled the slot and lost and cried, hey, I didn't know I was going to lose. Like now you may say the public should be protected against that. But meme coins are a dangerous.

Steve Inskeep: You said you made money on the Trump.

Dave Portnoy: On the Trump one, I did. I made about a million bucks.

Steve Inskeep: How'd you do that other than buy low, sell high? Was there some effect to it?

Dave Portnoy: That's just totally it. Like I think I bought it at 24. I went to bed. It was at 75. I said, get me out of this. And then I made a million, and I put on the Buffalo Bills to win the Super Bowl. So I'm back down even.

Steve Inskeep: Well, but you had a lot of fun.

Dave Portnoy: Yeah, it was a good ride.

Steve Inskeep: Let me ask about another thing in that barstool conservatism definition. Anti-authoritarianism. Does anything the president has done to expand his power or to reach for more power concern you?

Dave Portnoy: No, not yet. I agree with a decent amount of what he's trying to do. I'd have to get a specific example. There could be specific examples where you're like, I'm like, no, I don't agree with this one. But the things, I should add. Sending people overseas without court proceedings. This to me is a complicated issue because for the guy, and I forget his name, the one with the tattoos, but not the tattoos. The Maryland man, the Brego Garcia.

Steve Inskeep: Yeah.

Dave Portnoy: I think he's a bad guy. Like, I don't think he should be the one that Democrats are putting a flag in the stand and being like, what are we doing here? Even though they're like, well, you know, his tattoo meant something else. I think the tattoo, they didn't have the actual. But I think for that to be like your flagship guy, where I have the issue, you got to be right 100% of the time. Like, he I don't have a problem with. But God forbid you, and I don't necessarily think you should go back in time. Like, I don't think if somebody isn't here legally, but they're a productive member of society with no issues, I don't think then you go and say, get out of here. But if you've been committed of a crime or have something and you're here illegally, I don't have a problem with them getting kicked out of the country. I think that's okay. To answer your question, I don't have a solve because how do you do due process with all of them because you'll never get through it because of the time and energy it takes to do that go through the courts. So I'm stuck. I don't have an answer for you. You have to be right 100% of the time because the due process, how do you know? So I don't have the answer for you.

Steve Inskeep: That's you're right. You're right. I mean the court system is slow, it takes years.

Dave Portnoy: So but you can also churn people and hundreds of thousands of people can get deported every year. Yeah, so it can be done in the system. I don't think if you have a criminal record or you've done something illegally, I think this guy had a restraining order, his wife, and you're not here legally, then you shouldn't be in this country. That I have no problem with. How to accomplish that higher goal is a little more complicated.

Steve Inskeep: Bill Maher, who I think maybe is sympathetic with you in some of his positions, has been very critical of Trump but went to dinner with Trump and says he told Trump, you're scaring people. Do you think Trump is scaring people? And does it bother you if he is?

Dave Portnoy: He's definitely scaring people. He's definitely scaring people. But he was scaring people. He's been scaring people. How long has he been on the political scene now? 12 years? In this iteration, yeah. He was even doing things before. Yeah, so I think he's been scaring people throughout. I don't know. He scares my dad. I've said this many times. My dad is an anti-Trumper, hates him. Trump deranged him in syndrome. I think the fear is overbuilt. I also think a lot of it, there's no way for the toothpaste to go back in the tube. Like, he scares people. There's no, but Bill Maher's saying you're scaring people. I don't know what he would do differently at this point in the game to put people at ease. And I don't know that that's his responsibility necessarily to put, I mean, yeah, you want to unite the country. That was my number one thing when I said, if you said, Dave, what is your critique of Trump? I'd say he's intentionally divisive. Like that is something you want to bring the country together. But man, the people who don't like him hate his guts. Like they just, I feel like he could cure cancer and they'd be like, why didn't you get AIDS while you're at it? You know, I just don't think there's anything he could do that they would give him credit for, accept him for at this point. That that's his story on that is sort of written and he obviously digs in and trenches around it. Part of me I can see in that because if like you come at me I think unfairly, I like you're gonna get, I'm not gonna try to play nice with you. And he doesn't. Now I'm not the president, so that's an obvious difference.

Steve Inskeep: When you call your dad, do you talk politics or avoid talking politics?

Dave Portnoy: We got to avoid it. We maybe will last a minute and there's just no way he and I will ever see eye to eye on certain things ever. He considers himself the number one Trump expert in the world. He's like, Davy, I know Trump more than you. I've been following him my whole life and I know things you don't know and he's a bad guy. It just the people who he bothers follow him all the time. Yeah, paying attention all the. Howard Stern quote like the people love me listen for five, the people hate me listen for 10. But yeah, my dad qualifies for that. So my mom will put a stop to it. But I'm not one of those guys who sits here. Like my dad, I think really when he got elected, he's like, the world could not be here in four years. Like he could do something with this much power where we're just not here. I don't feel that way. I think Trump is a rational, sane guy. I actually think he's brilliant. But a lot of people hate things he stands for. They think he stands for it.

Steve Inskeep: Now, if you've been listening closely to Dave Portnoy, you've heard that he's for Trump, but not all the time. They're on every issue. And that raises a question on the minds of many Democrats. Could they win back a few more men? Some people have a break here, and then we'll ask Portnoy what he thinks Democrats could do.

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Steve Inskeep: Democrats, as you probably know, are asking, why are we doing so badly with men? We have this gender gap used to work for us with so many women. Now it works against us. They're having focus groups. They're commissioning studies. What would you tell Democrats to do differently, if anything?

Dave Portnoy: There's a lot of things, probably. It goes back to what you said, and I don't know if I have specific examples, but I really, truly feel like men have been, I don't know, demonized is not the right word.

Let me use an example of a story. This was from a Deadspin writer who hated our guts. Drew Brees, quarterback of the Saints, broke, I believe it was the touchdown record or the passing record, some big NFL stuff. They stopped the game. His family's on the field. And he says to his two kids, "See, boys, if you set your mind to it, you can do anything." There's a big think piece that he alienated his daughter by not including her in that discussion. Boys. Boys. He said "boys." His daughter was there.

It's like you've lost the plot of reality. Not everything is nearly as serious as it may seem. To me, again, guys can say a girl is pretty without being sexist. That doesn't make you a sexist pig. Simple things like that. It feels like you have to say things in hushed circumstances. Everything is blown out of proportion.

And my story probably makes me more sensitive to it, but you're talking about accusations. We had a story that people still bring up. The New York Times literally asked me for a quote about something the other day. I said, "I'd rather put a pencil in my eye than speak to you guys. I don't trust you at all." And they actually printed the quote, which I didn't expect. Dave's like, "We asked him for a quote. He said he'd rather put a pencil in his eye." And then the sentence below was that Dave has admitted to being a racist in the past.

What they're referring to is when Black Lives Matter happened, people who did not like me or Barstool went through every post, everything I'd done for 15 years. We had a Super Bowl party with Ja Rule and Ashanti performing. I do these emergency press conferences. It's like, "Emergency press conference, you'll never believe who we have at the Super Bowl party. I'm going to sing five songs for you. The lyrics, the first 30 seconds, you guess who it is." One of the songs, five years prior to BLM, had the N-word in it. I sang the lyric in front of the camera on YouTube, put it on. Didn't think twice about it. I won't do it again. Posted it. Nobody said a word in real time.

Five years later, this is what people say: "Dave's a racist." To me, if you can't look at intent and use some rationale, that shouldn't be the end of it. Like, am I racist? For the New York Times to literally say "Dave a racist" because of that incident, after 20 years of doing stuff, is wildly disingenuous. I think you can say I shouldn't have said the word, but it wasn't that big a deal, and I said I would never do it again. But there is context to things. There's more texture to things. A lot of times I feel like in this internet age, it has blown out... I mean, that clip still gets used against me if someone doesn't like me. I hear it every time.

Steve Inskeep: Does your story also suggest, though, that things are really not that bad for guys? I mean, you've done really well in life.

Dave Portnoy: Yeah, I don't know that it's bad. But I don't want to be demonized for it. And I want to say it's bad. I don't know that my story is an indication of anybody else's story.

Steve Inskeep: There was an episode that we don't have to totally recount, but somebody at a Barstool bar held up a sign that says "F the Jews." You had a very strong reaction, which is understandable, but over the top almost. What really set you off about that?

Dave Portnoy: It was probably building. I've been doing Barstool for 20 years. Since the conflict in the Middle East, the amount of anti-Semitism I deal with daily is astounding and growing. So it already caught my attention. The fact that it was so blatant, that it actually made it onto the sign in our bar, and somebody felt it was okay to do that, that someone put it on the sign, that nobody had a visceral reaction like "What the hell are you doing?" — all of that really, really, really bothered me.

So I almost film my unfiltered, candid reactions all the time. I could be watching a sports event. This pissed me off to no degree. So I picked up the phone and made a video of how I felt, and it turned into a days-long episode on the internet.

Steve Inskeep: Do you think it did any good?

Dave Portnoy: I don't know if it did any good. I think it raises attention to it a little bit. I've had plenty of Jewish people come up to me and just thank me. They're like, "Thank you for saying something. Not enough people are saying something." Whether it's true or not, I'm glad I spoke up.

Steve Inskeep: It is interesting that you spoke up because you have been a free speech guy.

Dave Portnoy: Still am.

Steve Inskeep: Not necessarily a contradiction in saying you disagree with somebody else's offensive speech. But is there a line you would draw somewhere between what's appropriate and what's not?

Dave Portnoy: I'm a big free speech guy. If you're going to put somebody in danger, like you can't yell "bomb" in an airport. You can't do that. That's not free speech to me. This, you can yell "F the Jews" or do that. Where I think a lot of, I would describe them as morons, confuse free speech with consequences for free speech. You can say whatever you want, but there are consequences to what you say. And that could be me airing you out, hoping you don't get a job in the future and things like that. People seem to confuse those two elements. I am fully free speech outside of "I'm going to murder you." That's not free speech. That's a threat. That's different. But saying "I don't like Jews" — I don't like you either, but you can say it.

Steve Inskeep: You started to run for mayor of Boston once upon a time.

Dave Portnoy: Yeah.

Steve Inskeep: You got screwed.

Dave Portnoy: Yeah.

Steve Inskeep: What happened?

Dave Portnoy: You needed 12,000 signatures to get on the ballot. I had a pretty well thought out plan because of all the colleges in Boston. I thought I could register them, get them to vote. The signatures can be thrown out for one of two reasons: you can't read them or they're not registered in Boston. We didn't do this ourselves. We paid a reputable firm to gather the signatures. They got 20,000 of them, and somehow only 11,000 of them were legible. So I think there was a concerted effort to keep me off the ballot.

Steve Inskeep: Have you thought about running again for something?

Dave Portnoy: Every once in a while it's fleeting. I think you can accomplish a lot more in the private sector than probably you can in the public. I think we've done a good job at Barstool with helping in the private sector, raising money at different times. I don't know. I don't trust those politicians. I feel like I go to a whatever and really get frustrated with everything.

Steve Inskeep: I'm sitting here thinking, you're pro-choice, so you would have trouble running as a Republican in most places.

Dave Portnoy: Yeah, I'd have to be.

Steve Inskeep: And you're not a Democrat, that's for sure.

Dave Portnoy: Yeah. Growing up, I would have said I think libertarian is probably more where I'd fall. The problem is the political party. I think people are craving what I would say is fiscal conservatism and social liberties. I think that is the majority of the country, actually. I think that party, if that party was like an established party, I think that candidate would be very strong.

Steve Inskeep: I think about people in my family that I grew up with whose views are a lot like yours, and they're basically Republicans and basically vote Republican, but they think about it. And when you talk with them, you find out, well, this guy voted for Obama once, and this guy voted for Clinton. Have you voted for Democrats? And would you vote for a Democrat?

Dave Portnoy: Yeah, 100% I would vote for a Democrat. And I have voted for a Democrat. I campaigned for Paul Brown back in the day. And I've said this mindset: what the Democrats lost themselves, the election with this whole Biden cover-up of him — I don't know, I call it dementia or whatever it is, cognitive disabilities, fading, whatever you want to call it. I was talking about that for two years. I think to an intelligent mind it was quite obvious. And if you said it, and not like somebody like me but like you, that old interview with Lara Trump with Jake Tapper where he's screaming at her for even insinuating it — that type of attitude and the way they handled the election is why they lost.

What drives me to make rants on social media and Instagram is I feel as though the left will look at you with a straight face and say they are the moral clarity, moral compass, moral superiority. And it's like, well, you've been lying for like two years to our faces about this. You may not like Trump, and people always say lies. I think most of his lies tend to be crazy euphemisms, like if you win a game by 20, you say 100. I think they've been far more honest with the American people.

Steve Inskeep: Do you believe he's won all those club championships that he says?

Dave Portnoy: Well, I don't know. Do you think Putin or Kim Jong Un shot like an 18 on a full regulation golf course? I mean, he's a great golfer for his age.

Steve Inskeep: Have you played with him?

Dave Portnoy: No. I've seen the clips.

Steve Inskeep: In the clips he would have...

Dave Portnoy: That was the funniest. And I do find comedy in politics. That whole golf debate between him and Biden, I thought was some of the best comedy material we've had in a long time. I'm going back, that was the high point of that otherwise low debate. And it was the only thing that Biden really got under his skin about, what he said about his handicap. So take the small victories there.

Steve Inskeep: You probably know that in surveys, most people do not like the direction of the country. It's true last year, it's true this year. Sometimes it goes up a little, sometimes it goes back down. How do you feel about the direction of the country and where we're going?

Dave Portnoy: My biggest... I think Trump is doing what Trump wants to do. I want a United States. And when I say that, people don't hate each other. And I do feel like we've lived in a world where there's a lot of hate in this country based on groups, sectors. Maybe I'm wrong. I've said it probably 10 times during this interview. I do think we're far more alike than we are not alike. But it seems like the differences are what has carried the day for a long time. And if you turn on the TV or the news, maybe that's always been the case, maybe that's the internet age. Sometimes I can't tell. Something that you may not even know about gets blown up on social media. But I wish we got along more. That would be my biggest concern as somebody that sees there's just so much hate.

Steve Inskeep: Dave Portnoy, it's a pleasure talking with you. Thank you.

Dave Portnoy: Thanks for having me.

[Musical break]

Steve Inskeep: This has been a special edition of Up First from NPR News. We visited Dave Portnoy in the 305 Podcast Studios in Miami, where they moved aside a few of the plants to make space for us. Our producer is Adam Barron, our editor is Rina Advani, and our executive producer is Jay Shaler. I'm Steve Inskeep.

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