In today’s episode of Winner, Winner, I’m in conversation with Cait Conley, who’s running for Congress in New York’s 17th congressional district against Republican Mike Lawler.
Cait is a decorated Army veteran and national security expert. A fourth-generation Hudson Valley native, Cait served 16 years in the U.S. Army with six overseas deployments and later led counterterrorism efforts at the National Security Council and election security at the Cybersecurity and Infrastructure Security Agency. She’s been a mission-driven, independent leader focused on protecting democracy, lowering costs, and strengthening critical infrastructure, bringing real-world experience to the fight to deliver results for working families.
New York’s 17th congressional district is located in the lower Hudson Valley, just north of New York City, spanning Rockland and Putnam Counties and parts of Westchester and Dutchess. It’s a highly suburban, affluent, and diverse district with an economy tied to finance, healthcare, and professional services.
Politically, NY-17 is one of the nation’s most competitive swing seats: it’s rated near even and has recently voted for both parties in top races. NY-17 has a PVI of D+1, and Harris won the district by less than a point in 2024.
The district is on the DCCC’s Red to Blue list for the 2026 election cycle.
You can watch the episode here.
I asked Cait about what her message is to win in this district and why she’s the candidate best-suited to flip this seat in November.
When I look at this, it’s the same way I looked at service in uniform. You’re out there fighting for everyone. When I was out there putting my life on the line for our community, for our country, I never cared if someone was registered for one party or the other, or even if they voted.
What I cared about was they were here, and my job was to protect them. And so for this, I look at it the same way: Government’s job is to deliver for the people, not a party, not people of a party, but people. And we’ve gotten way too far away from that.
My frustration with what is going on is it’s not just because of Trump and this administration. Don’t get me wrong — there is a lot of that. But it’s also because even before Trump, things were broken.
And so to your point on what is my message to win, 28 percent of registered voters in New York-17 are unaffiliated or independent. A Democrat or Republican cannot win this district with just their registered voters alone. You have to have a candidate who is going to get voters to choose them as a person, not just a party. And so my message to them is, “I want to be your fighter.”
I know you’re frustrated. I know things have gotten really, really hard. And government has failed. I know you feel like America no longer works for working families. And you’re right. And my commitment to you, as someone who’s grown up in these working class families, is I will go in there every day and make sure we fix what is wrong. That we focus on delivering, not excuses. And that’s the lifestyle I come from. You don’t get to hide behind excuses and, “oh man, I wish it had happened this way.” Where I come, the stakes don’t get any higher, and you find a way to still succeed. And so for this district, service matters. I don’t like to quote Mike Lawler, but I quote him here because it’s part of how I’m going to beat him: He talks about how New York-17 is “a district of heroes,” where over 50% of households are either veterans, the family of veterans, first responders, or the family of first responders. And so, Lauren, when we talk about service and the reflection of character that service means, the Hudson Valley gets it.
I went into service because of these communities in the Hudson Valley. And that’s going to be a big part of earning their trust.
If elected, Cait would be part of what could be a majority-Democratic Congress. I asked her what she thinks should be the message from Democrats about meeting voters’ needs and how she thinks elected Members of this next Congress can prove the Democratic Party can be effective leaders for this moment.
We have to focus on working and delivering. “We are here to work and deliver” must be our North Star. And we have to actually be true to that, not just in words and slogans, but in actions.
We talk about how the Democratic Party has lost so much of this country, but we have failed to communicate effectively, using both the wrong messengers and the wrong messages. We haven’t delivered in a way that has actually made people’s lives better, so I think we have to be more than just slogans and truly recognize we’re in this place because we, too, have failed to meet the moment as a Democratic Party and must do better. And if we do that — if we follow through, if we deliver — then we earn the trust of people and their support; we get them to believe in the institutions again.
I think that is essential because right now you are seeing Americans losing faith in the American government and apathy taking hold. I do believe the Democratic Party has tremendous opportunity come this November, but where I caution everyone is just because you see frustration and anger toward one side doesn’t mean people are automatically supporting the other side. And it is this distance that we must close. This is the work that we must do to bring people over. That is about us showing up and being those leaders that the people deserve and need.
We have to deliver no matter who is sitting where. And in that way, I think it’s not just about a single leader. I think it’s about having the right people who can speak on the right message and carry the level of credibility necessary to help bring the American people along.
I think for too long, the Democratic Party has had this strategy in its communications where it’s like, “oh, if we’re right, people will follow.” And I’m like, “no, no, no. If you want to be effective, you’ve got to bring people along.” And so that has to be our focus: on how we move forward.
Lastly, Cait and I had a conversation about why it’s so important to be a depolarizing presence in politics when so much of the political environment is so polarized.
Right now, polarization, I think, is the biggest reason our nation is failing. We have seen how partisanship and this degree of polarization has torn apart not just this country, but communities and families.
We have to get back to the point where I believe this nation is at its best, which is when we have two healthy political parties. They can differ on the path, but we share a goal of what’s best for this nation and how we get there, which is America at its best.
This Republican Party is not the real Republican Party. It is a MAGA cult loyal to Donald Trump, not this country, not service, not the people. I’m sorry to say that, but that is the reality we are facing. I hope that gets fixed. But right now, that is broken. And so I do believe we need leaders to step up who say, “I don’t care how you politically identify. What I care about is that you’re a member of our community, of our country. And we owe you better.”
When you look at us as a nation, we share so many of the same values, far more that unify us than divide us. We just keep focusing on the differences. And that can’t be the way forward. Because at the end of the day, we’re neighbors first; we’re Americans first — not Democrat or Republican. I believe we have to get back to that.
That’s what it’s like in the military: In the military, it’s about the mission. No one cares what color you are, if you’re a man or a woman, what your political affiliation is. They just care that you’re there, and you’re there to serve, and you’re going to have their back.
I believe the way we tackle hard problems is by coming together and being willing to work together to find the right solutions. And that can’t happen if we continue to be just these polarized echo chambers that would rather yell and complain and get angry instead of solve things.
What gives me hope is the fact that the majority of people are sick of it, too. People are fed up. They don’t want more tearing at one another; they want government to do its damn job. They want people who are going to solve problems and be serious professionals who are trying to do the hard work. That is what gives me hope as someone who has spent over a year on the trail, going to every corner of this district — a district that I believe represents so much of America.
People want better, and they know they deserve better. And better means focusing on the mission. And in this case, the mission is making sure America’s best days are still ahead of us.
Mike Lawler is one of the most bipartisan Republicans in the House. He has even filed a number of discharges against his own party. So I don't know how Cait thinks she can do more to depolarize than he has.