PHILADELPHIA—This guy I went to high school with lives several blocks from our old school. He saw my post on Facebook that I was in town and he shot me a text Tuesday morning. Our parents used to live a few miles from each other in the Philly suburbs, but I hadn't seen him or even really spoken to him in many years. I asked him if he was free to meet for a beer.

So we sat across from each other at a table at a corner bar not far from our old high school and talked about what we've been up to, and who in the class is now married, and who has kids, and who served in the Middle East, and who moved away for a few years then came home. Then I pulled out my tape recorder and asked if it was ok to hit record, and he said yes, and we started talking about the election. What follows is that conversation, edited for clarity.

So are you a registered Republican?

Yes.

Since when?

Probably since I got my license. Since I turned 18, I guess. Only voted once. It was the reelection of Barack Obama, last go-round.

2012?

Yes.

Who'd you vote for?

I did not vote for Barack Obama. I voted for Mitt Romney. I had to go to a car dealership. I voted. I walked out of the booth. Someone asked me if I was voting to support the president, and I told them, "You have a better chance of me buying a new car today." Just wasn't a fan. I'm Irish. I realize the world's gonna break apart, so, I was hoping for McCain four years earlier, was hoping for Romney, and Barack got elected. Do I hate the guy? No, I don't hate the guy. It's the president. I respect the president. I respect the office. Love the country.

Do you plan to vote for Trump?

Yeah. As of today, I think that where I'm gonna end up casting my vote is Donald Trump. Gary Williams looks pretty interesting.

Gary Johnson?

Yeah, whatever. I played a lot of lacrosse in college, took a lot of hits to the head. Gary Johnson, yeah. Bill Weld. I think their marketing platform is really interesting. Especially on social media. I think they really are doing a good job at capturing those people that are like, "I have to vote for one of two idiots, who am I gonna vote for? Oh wait, these guys actually have good resumes." But yeah, I think I'm leaning more towards the Donald. Do I think he's gonna build a wall? No. Did building a bunch of roads and bridges take this country out of a tough time decades ago? Yeah. Building a wall, will that take us out? I doubt it. Do I think it's gonna happen? No. Is Mexico gonna pay for it? Doubtful. Does it sound kinda funny? Yes.

What is it about Trump that appeals to you?

His brutal honesty. I feel just very hesitant with Hillary with regards to her honesty. John, if you and I click on an advertisement on the wrong side of a web page, we're gonna get a year's supply of Viagra. Are you telling me she didn't see the word "CLASSIFIED" at the top of a piece of paper and decided to send it out to people from her Gmail or Yahoo account? Come on. I'm not the brightest bulb in the box, but even I know that's stupid.

I'm not the brightest bulb in the box, but even I know that's stupid.

So is it a matter of supporting Trump, or is it a matter of disliking Hillary?

I would say 60/40. Distrusting Hillary, not disliking. I have a lot of respect for where she comes from. I'm thrilled at the opportunity for our country to nominate the first female candidate for the presidency of the United States. Do I think we need a woman president? We don't need one. Would it be great if we had one? Absolutely. How many other countries have a supreme leader of the female variety? We're about due. Do we need the right one to be the first one? Preferably. But nominating and electing for the sake of sex, that's naiveté, in my opinion. We could have a robot for all I care. As long as they do right by the country and do right by the people, I'm ok with it. But yeah, 60 is distrusting, not disliking, Hillary. Forty is siding with Trump.

When you talk about these things at a bar with your friends, what do most of them say?

Well a lot of our, my friends come from our background. You know, upper middle class, white, educated parents that live out in the suburbs, where they sent their children to private school, where taxes continue to rise. For instance, my parents live in one of the highest-taxed school districts in Pennsylvania as well as in the U.S., and our high school in that school district is a dump. Taxes continue to rise in that area. So a lot of people in our age group are voting with their parents, to be absolutely honest with you. Especially the ones that just aren't politically educated. I went to school in D.C., but I didn't take note of politics. Only time I took note of politics was when the inauguration was going on and I had off from school. (Laughs.)

Are your parents, and your brothers, and your extended family, are they going to vote for Trump?

I don't know. I think it's like, it's a firecracker. We don't trust her. We don't want her. Do we have to go with him? That's a sad state of affairs for the election, in my opinion.

Do you feel obligated to vote at all?

Yeah, I think I do. I really had some Irish guilt about that first election I didn't vote in. Whether it be the people with the clipboards out in the park asking, "Are you registered? Did you vote?" And I didn't even take the time to fill out the absentee ballot because I was down at school at the time. So, you know, I definitely feel obligated to vote this go-round.

Pennsylvania is historically blue. Do you think your vote will matter?

I think every vote matters. There's no reason why any vote shouldn't matter. Whether it be the trust fund wealthy or the poorly educated. Everyone has stake in the game.

What do you make of Philly and the DNC? As a lifelong person who's been here, do you feel proud of Philly to be hosting Democrats? Do you feel annoyed by the people you see around the city?

I'm a Republican capitalist, John, to be absolutely honest with you. I think that alumni from our high school are in the mayor's office and they made sure that, hey we had the Pope come to visit and we had the DNC. I think it's awesome for business. All of our hotels are filled this week. All of our restaurants are packed this week. I have friends who work in event planning, and they hit their quotas. They're doing extremely well. The city has a lot to offer from a tourism standpoint. It just puts us again on the map. It's awesome. Yeah it's a nightmare for traffic, but at the same time, the tax dollars that were brought in, and the police force, they get, you know, they get to work. Our police force is fully utilized. I could care less if it's the Democratic Convention or the Republican Convention. Am I going to welcome something that's hateful or non-welcoming to any and all observers? Am I gonna welcome a KKK rally? No, I'm not gonna welcome one of those.

Timothy A. Clary Getty Images

Did you watch the RNC last week?

Yeah, I watched a little bit of it. I watched a little when Donald spoke.

What did you think of it?

I was interested to see how his son painted him. I was definitely interested to see how his daughter painted him. Definitely got a good chuckle out of his wife's speech, you know, Michelle Obama's. I don't know if that was an inside joke or what. You know, certain Republicans think that Donald's been planted by the Democrats to get Hillary elected. And Hillary's claiming the Russians leaked those emails to get Donald elected. It's a pretty good game of Clue. I'm waiting for Colonel Mustard with the candlestick to show up.

One of the principle themes of his speech was law and order. In terms of both the local level, where he talked about the attacks on police in Dallas and Baton Rouge, but also on the national/international level, in terms of terrorism, in terms of immigration, Syrian refugees. Of course, he's said he wants to bar Muslims from entering the country.

Yeah, that goes up there with the wall. Do I really think he's gonna put a wall up? No. Do I really think he's gonna stop everyone who practices the Muslim faith from entering this country? No. Do I think we need extreme reform? Yeah, I really think we need to stop putting one hand towards the finish line and waving everyone in. I applied for Global Entry. I have to go to the airport and submit myself to an interview. I think at the very least an interview needs to be conducted. I think at the very least some background needs to be done on where these people have visited and where they come from.

What people?

People that are coming from these war-torn countries. Do I think that we need to help? Absolutely. But at the same time, you're subjecting certain countries, for instance, Germany had their second attack this past week. It was from an individual who had mental illness, who wasn't able to be deported because he had mental illness, but was listed for deportation at least once, and it's like, that's a powder keg that was put into the corner. Because of that, individuals died.

The beginning of your sentence there, you said, "Do I think he's actually gonna check everyone? No. Do I think he's gonna build a wall? No." Why would you vote for somebody who says they're going to do things that you don't think they're going to do?

(Long pause.) Bernie Sanders and certain individuals told me that I was gonna go to college for free. Do I really think I'm gonna go to college for free? No. There's just those empty promises. We all thought we were gonna get free healthcare, too. People aren't going to the same doctors that they grew up going to. I think that's just a matter of the political game.

What do you think is the defining issue of this election? Or the biggest issue facing the United States right now?

Government spending. Government debt. It's one of the main things that, sadly, I lean towards Donald. It's weird like, I'm ashamed to say I'm voting for him, but I'm probably gonna vote for him. He looks at that number of our nation's debt and is like, "Whoa, that's not good." She looks at it like, "It's there, I can't cut it, if I cut it it's going to hurt us." No, there are ways to cut it. There's excessive spending going on. I remember driving on various highways here in the mid-Atlantic and seeing like the "road rejuvenation project funded by Barack Obama." We spent 13 million dollars on those signs alone. I'm throwing that number out there. It was in the tens of millions of dollars. In the teens. Shit, we spent that much money just to promote the fact that we did it? Why did we do that? Just do it. Do I really think we spent 4 billion dollars on a website for Obamacare? No. Do I think Donald Trump spent 3 dollars on his website? No. Do I think there was probably a smarter way to do it? Yes.

What causes you shame to say you're going to vote for Trump?

Guy had a show called The Apprentice where he used to fire people. It's not shame, it's just like, it makes me giggle. I would say shame's not the right word. I hope you don't quote me on that. It just makes me giggle to say "I'm throwing my hat towards that guy." You see those videos of him on WWE Raw, body-slamming Vince McMahon. Buzz-cutting Vince McMahon. But at the same time, you know, Hillary's had those funny things. Bill playing the saxaphone in a pair of Ray-Bans always makes me giggle, too.

It's a pretty good game of Clue. I'm waiting for Colonel Mustard with the candlestick to show up.

You mentioned the spending of the Reinvestment and Recovery Act, on the signs…

It sounds a lot more smarter when you say it than when I do.

And on the money for the Obamacare website. There are a lot of different numbers that float around. It's hard to tell what's what. Where do you get most of your news?

Two people that I trust most with regards to political conversation are my dad and my older brother. I'll always remember my older brother saying, "I get more news from Jon Stewart than Fox News or MSNBC." I think John Oliver is a great alternative. Jon Stewart's replacement is pretty good. I get a lot from those shows. You know, I do watch CNN, I do watch Fox News. You know, we always joke, we're a Republican household. Do we only watch Fox News? No. But we jokingly refer to it as "Channel 1."

Those guys, though, Jon Stewart…

They HATE Trump.

They destroy Trump. So if you're getting news from them, is that causing any concern?

Not really.

What do most people on your Facebook feed seem like and sound like? If you see political views floating by, where are they?

Bernie. Yeah. A lot of Bernie. A lot of Bernie and a lot of Trump. Not many Hillary. It's ridiculous. This is the first time I've actually ever thought of it. It's a healthy mix of strong Republican, Democrats, straight, gay, religious, non-religious, and to be absolutely honest with you, it's stick to the Republican line, or Bernie Sanders was cheated.

It's that binary?

Yeah.

Things are so far apart.

And little-to-no mention of Hillary unless it's like the funny meme.

So you're 28?

Twenty-eight years old.

Are you where you thought you would be at 28? In terms of career, money, quality of life?

That's an interesting question. Where I am with my career, we always joke about it, we always want more. That's the Prep mentality. It always wanted us to want more. Am I doing well compared to my counterparts? I think so. You know, I bought a modest condo a year ago. I'm pursuing a masters in business right now. I work for a Fortune 100 company. I'm able to provide for myself. Now, I'm beginning to think about marriage, providing for myself and my girlfriend. Do I wish I could have more? Yeah. Do I hate the fact that I have student loans with interest rates between seven-and-a-half and 10 percent? Yeah I hate that. Do I always remember the moniker like, stop treating students like cash cows? And giving banks zero percent interest loans? It sucks. Do I make my loan payments on time? Yeah. Are they in deferment right now? Yeah, but I still pay 'em. I paid loans off for my high school education, too, that were in my parents' name. I paid my parents back for high school loans because my dad didn't go to college. He worked manufacturing jobs. My mom worked two nursing jobs and sent three boys to private school and sent all of us to private Catholic school for undergraduate. Did I pick my college based on the number of scholarship dollars? Absolutely.

Do you think that electing Trump is going to improve your life? Or the lives of people that are not you?

It's a team sport for me. I think it's best for the country. A lot of the statistics and figures he throws out there sound dopey, but I agree with the fact that he says the unemployment rate doesn't include people who stop looking for jobs. It's not as low as it is. It's a lot worse. I think companies that have left this country and seek tax shields in other countries deserve a slap on the wrist. But at the same time, as a country, we haven't welcomed business. We haven't welcomed manufacturing companies in this country. We have individuals that have, with high school education or lower, that could make a living for themselves or a life for themselves, and instead are seeking other avenues, both legal or potentially even illegal, that harm this country. I think a strong America is a working America. A strong, working, low unemployment country is the best bet. I think additional government spending and programs that don't produce jobs are not the right direction for this country. But if Hillary gets elected this week, and she gets everyone back to work, I'm all for it. It's just hard to trust any word she says nowawadays.

What would you say to her if she walked in this bar right now?

Hello Secretary Clinton, can I buy you a beer?

What would you say to to Trump?

Hello Mr. Trump, how's your golf game?

He doesn't drink.

Does he?

He doesn't drink alcohol or coffee. And he says he's never smoked or done a drug. Do you believe that?

It's one of the things I liked about Obama. He admitted to smoking and he admitted to inhaling. At least he was honest about it.

John Hendrickson Deputy Editor John Hendrickson is the Deputy Editor of Esquire.com, where he oversees the site's 24/7 news operation as well as all politics coverage.

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