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Next Question with Katie Couric

George Conway's Political Transformation

Next Question with Katie Couric

Katie Couric Media

News, Health, Society & Culture, Commentary, Documentary,, Health & Fitness

4.4 • 4.7K Ratings

🗓️ 14 May 2026

⏱️ 70 minutes

🧾️ Download transcript

Summary

Once a loyal Republican who celebrated Donald Trump’s 2016 victory, George Conway is now one of this administration’s most outspoken critics and a Democratic candidate for Congress in New York’s 12th District. In this candid, wide-ranging conversation, he sits down with Katie to discuss what motivated him to run for office and why this moment requires more than commentary and criticism. He traces the early days of the first Trump administration, when he began to see something he could no longer ignore, and how that realization reshaped not just his politics, but his personal life, including his high-profile marriage to political consultant Kellyanne Conway. Along the way, he examines why so many Americans remain loyal to Trump, drawing on psychology, identity, and what he calls a growing “permission structure” for division and resentment. Ultimately, he sees this as a moment that demands engagement, not passivity, and one that will help define the future of American democracy.

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Transcript

Click on a timestamp to play from that location

0:00.0

You know, there are two reactions to Trump that you could have, and you can see how some people had one and some people had others.

0:13.9

It's like nails on a chalkboard. Some people kind of can get used to the screeching and the noise and others.

0:20.4

It drives them to do something to and the noise and others it drives them

0:21.0

to do something to leave the room.

0:23.6

And I was one of the people that it didn't take much.

0:27.1

And ever since then, it's, you know, I've rethought everything, rethought everything about

0:32.3

my understanding of human nature, rethought everything about what, you know, what the purpose

0:36.8

of the whole governmental enterprises, rethought everything about what, you know, what the purpose of your whole governmental

0:37.8

enterprises, rethought everything about, you know, what's the importance of, like, empathy.

0:46.9

Hi, everyone, I'm Katie Couric, and this is next question.

0:54.1

George Conway is not your typical Democratic congressional candidate. In fact, until just a few

1:00.4

months ago, he wasn't a Democrat at all. And now he's running to represent New York's 12th

1:06.4

district as one. For decades, he was a conservative Republican, a top lawyer, a proud member of the

1:12.8

Federalist Society, and someone who celebrated Donald Trump's 2016 victory. He was even considered

1:19.4

for a role in Trump's Justice Department. But instead of joining the administration, Conway became

1:26.1

one of its fiercest and most relentless critics.

1:30.0

That opposition didn't just come to define his public life. It also reshaped his personal one.

1:35.8

Until a few years ago, he was married to Kellyanne Conway, who managed Trump's first campaign

1:40.8

and became one of his most loyal advisors. Their political divide played out in real

1:47.0

time in full public view, with Donald Trump himself, once calling Conway a stone cold loser

1:52.8

and husband from hell. Now, after years on the sidelines, as a legal and political commentator,

2:00.0

he's stepping into the arena himself

...

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