David Urban has been credited with helping then-candidate Donald Trump win the 2016 presidential election. As a former senior advisor on Trump’s 2016 campaign, Urban played a pivotal role in Trump’s strategy in Pennsylvania, one of a handful of swing states that also proved to be crucial in the 2024 presidential election. Urban’s resume has run the gamut. Prior to his political career, he attended the U.S. Military Academy at West Point and earned a Bronze Star in Operation Desert Storm. Now, he can be seen on CNN as a conservative political commentator.
N Magazine: How did you discover Nantucket?
David Urban: I came in for a wedding and stayed at the White Elephant 30 years ago. My wife and I live in Florida. We were looking at places—Martha's Vineyard and Newport and Block Island and Maine. Post-COVID, we came up, and we were hooked. We kept renting, until it became apparent that buying a house is much more cost-efficient than renting.
N Magazine: You were instrumental in Trump’s victory in 2016. How surprised were you that Trump won that year?
David Urban: When you’re traveling around a big state like Pennsylvania, you talk to people. I’d pull into a gas station [in 2016], and everyone talks about the election. I would say, “Well, who are you going to vote for?” Everywhere I went the answer was, “Trump, of course.” The vibe on the ground was, “Something’s going on here, something that’s different.” So early on, I knew that this was not a normal race. In 2020, I didn’t get that sense. I said to [Trump], “Listen, I’m not feeling it,” and he said, “You think Biden can really beat me?” I said, “Yeah, I think he can.” I said, “Listen, you’ve had nothing but negative press for four years. The kind of legacy media just beat the hell out of you, and we’re in the middle of a pandemic, like a black swan event where people just want change.” I said it’s going to be 50,000 to 75,000 votes in one way or the other, so we need to keep fighting here, and sure enough, Trump won Pennsylvania by 45,000 votes in 2016, and lost by about 80,000 in 2020.
N Magazine: You remained steadfast that Trump would win the 2024 election and potentially win big. What made you so convinced?
David Urban: You start to know the market conditions. I knew from being on the ground in Pennsylvania and talking to people, and I knew the corporate media narrative did not match what I saw on the ground. The pollsters kind of missed it, and I think people weren’t necessarily telling them the truth. When people don’t tell you the truth, it’s hard to poll. Pollsters might miss that, but when you’re on the ground, you don’t miss that.
N Magazine: If you were a leader in the Democratic party, what would you say to the party about its focus following the election?
David Urban: Some Democrats say they lost because they weren’t progressive enough. Clearly, that’s the wrong answer. The most Hispanic county in the United States had a 72-point swing for Trump from 2016 to 2024. What’s going onto make us see that kind of change? I think it’s largely due to the economy. If you’re an average person and bread and milk is three times more expensive, you’re getting frustrated. Democrats are talking about democracy and these lofty ideas, but people are more concerned with kitchen table issues that affect them. I think with the economy and social issues, Democrats are out of touch with where people are. The Democrats thought abortion was going to be the biggest issue in the world and that it was really going to dominate. It was a dominant issue in the 2022 Midterm Elections, but it’s a more distant issue than the economy.
N Magazine: Does this election help launch Pennsylvania Gov. Josh Shapiro’s run for president?
David Urban: He’s a friend of mine. I think he’s an incredibly gifted politician. Other Democrats like Gretchen Whitmer, Gavin Newsom or Wes Moore don’t have the political background or talent that Josh does. He’s wildly popular in Pennsylvania and I suspect that he will find a way to work with Trump. That will only reinforce his standing among Pennsylvanians. While Democrats lost, Josh Shapiro won.
N Magazine: Would you accept a spot in the Trump administration?
David Urban: No, I’m an outside guy, not an inside guy. I enjoy being able to have a little bit of input and a life. Being a public servant is incredibly hard. The time span of the people who go into these jobs is about 18 months because it’s all-consuming. They don’t get a break. There is no break for the weary. It’s 24/7. You go in to work for these jobs that are woefully underpaid, incredibly overworked, and at the end of the day, nobody thanks you. Nobody says, “Hey, David, you did an incredible job today.” You get torn to shreds because you’re trying to help our country.
N Magazine: Let’s talk about you personally. You were recruited to play football at Harvard. But you chose the U.S. Military Academy at West Point instead. Was that a difficult decision at the time? And in hindsight, what was the meaning of that decision?
David Urban: I was recruited by Harvard’s famous coach, Joe Restic. Joe Restic was to Harvard as Bobby Bowden is to Florida State, or Nick Saban is to Alabama. But it was a pretty easy decision. I visited Harvard with my best high school friend who is now a tenured professor at the Harvard Business School. I remember we went and visited Harvard together. He said, “How about going to West Point with me?” And I said, “That’s fine.” It was a whole duty and honor [for] country thing. I viscerally felt it was just the place for me. When you go there, they had a big poster at West Point that said, “Most of the history we teach was made by those we taught.” They have Robert E. Lee and Ulysses S. Grant and Gen. Douglas MacArthur, and all these famous folks up there. And you thought, “Wow, I want some of that.”
N Magazine: You earned a Bronze Star in Operation Desert Storm. How do you describe your military experience?
David Urban: There are two types of Bronze Stars. One is for valor, for something like jumping in front of a hand grenade. And then one’s for doing really great stuff while in combat. Mine was for achievement, not for valor. I always want to make sure that’s correct, because I never want to be in a position like some people we find in the media today who are claiming things they’re not. There are so many people who are super heroic, and it’s still red, white and blue. I’m very proud of it, very proud of what I got it for and what I did. The military is about grit, hard work and teamwork. It’s about the golden rule—treat others like you’d like to be treated. Success in the military is no different than success anyplace else. If you’re the lowest private, you’re treated the same way as the chief of staff of the Army or the chairman of the Joint Chiefs of Staff, who I’m good friends with. These are the best people that America has to offer, who are your colleagues, your peers, your employees.
N Magazine: How would you describe the state of our military preparedness now?
David Urban: I know Mark Milley, the former chairman of the Joint Chiefs of Staff; Charles Q. Brown, the current chairman of the Joint Chiefs; Randy George, the chief of staff of the Army. Mark Esper, the former secretary of defense, was my good friend. The [former] secretary of the Navy, Richard Spencer, and [former Secretary of the Navy]Kenneth Braithwaite. All these folks are people that I know, and so I’ve got a better than average comprehension. I think our military today is probably the best military, best fighting force, the best men and women, the best trained, the best equipped that we’ve ever had in the history of our country. They are incredibly talented. They are loyal. They’re very smart. They operate at a level where most employers would kill to have these folks working for them.
N Magazine: You’ve had experience in the Persian Gulf and have observed what’s going on in the Middle East. What is your opinion as to where we go relative to Israel’s war with Hamas and growing tensions in the Middle East? How do you get a permanent solution?
David Urban: To see how perverted—and that’s the only way to put it, perverted—that Hamas has made Gaza and Gaza City, and what they’ve done to the people there, it’s just a shame. It really is a shame, because the Palestinian people do not want to have the outcome that they’re living through right now. If you pull the thread, it all goes back to an emboldened Iran funding and fueling Hamas and then Hezbollah [in Lebanon].It comes back to our relationship with Iran, and I do lay this at the feet of the Biden administration of being too soft on Iran and kind of opening back up when they lifted sanctions on Iranian oil, on the purchase of Iranian oil. I think the solution is to have incredible sanctions. Make them a pariah on the world stage. We need more sanctions on Iran, not less sanctions, because they’re going to find a way around even the sanctions we put in. The sanctions were working under the Trump administration. When you lift your foot off the brakes and put on the gas like we did, you see the results. I think you trace a line from the actions of the Biden administration to where we are today.
N Magazine: Let’s talk about CNN, not a bastion of the right, yet you are a prominent voice there. You’re the Trump guy. What is that experience like?
David Urban: It’s great. Mark Thompson, the CEO, isa great guy. He’s really supportive. Scott Jennings, my colleague, and myself are the two Republican pillars. There are some other folks they have, but we’re the people that get the most rotations. I think CNN is very fair to me and to my Republican colleagues because they give us a lot of air time. They give us a chance to make our point, and it’s incumbent upon us to deliver. Is it more difficult sometimes when it’s David Urban versus a host and two other panelists who hate Trump and a clip teed up that’s the worst possible clip they could have? There’s no clip that’s teed up about Trump that’s great. It’s always the worst Trump moment, and then it’s, “David, how can you defend that Trump moment?” That’s where it’s tougher. I accept the challenge.
N Magazine: What are you most optimistic about over the next four years? What are you most pessimistic about over the next four years?
David Urban: I am concerned about our debt. We keep whistling past the graveyard. As long as the U.S. Dollar is a reserve currency, we’re great, but the second that starts being questioned because of our incredible deficit, we’re in trouble. If global markets think we’re a risky place to do business, that really impacts us. I think we need to promote a dollar-based stable coin globally that can be traded. As payment systems become frictionless and people get on blockchain of payment, I think we need to make sure we’re at the forefront of that like we were at the forefront of the internet. I’m also concerned about the division in this country. No matter who won the election, half of the country was always going to be disappointed .I would hope the winners would afford some grace to the losers, and the losers would extend an olive branch to the winners. We may not agree on how we get to the destination, but we’re on this journey together. My biggest fear is that political violence will reemerge, but I’m now hopeful that we can strike a middle ground, and that President Trump will realize his place in history. This is an opportunity to cement that and build a Rushmore-like legacy. I do believe America’s best days are ahead of us. You see rocket launches and the promise of artificial intelligence and how it can help us. There’s so much in the future that’s so positive that we can corral.