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'The Big Break' reveals how D.C.'s oddball influential players gamble and schmooze

SCOTT DETROW, HOST:

In his new book, Ben Terris profiles Beltway power players to tell a story about Washington and the culture that drives it. It's called "The Big Break: The Gamblers, Party Animals, And True Believers Trying To Win In Washington While America Loses Its Mind." And as the title suggests, it's filled with some pretty interesting people.

BEN TERRIS: Sean McElwee is this fascinating character in Washington, a rising star Democratic pollster, started an organization called Data for Progress. He had been kind of a big deal in Democratic politics as a socialist, democratic socialist type, hosting happy hours in New York City when he lived there. He's become a more pragmatic member of the Democratic coalition now that he's moved to Washington and doing polls that the Biden White House loves.

DETROW: But as we soon learn, not everything is as it seems. Terris explains why he took this approach.

TERRIS: The point of the book was to find people that most American ones have not heard of, right? I mean, Washington is filled with characters who are unbelievably interesting, filled with drama, filled with intrigue. And so much of the Washington, you know, book genre focuses on very specific people, famous people.

DETROW: Yeah.

TERRIS: And I wanted to find people that, like, you know, evoked what Washington was really like in an interesting way and could feel new. And Sean was one of these great characters in that way. He used to be the abolish-ICE guy, and then he became the please-stop-saying-defund-the-police guy. And so I thought that made him interesting in general. But then in spending time with him, I found out that he was actually much more interesting than that and for reasons that he probably wished were not interesting, including a gambling habit. You know, I'd go to poker games at his house, and the gambling he was doing often had less to do with cards and more to do with politics. He was a pollster who bet on elections, including elections he worked on, including against candidates he worked for, kind of a Pete Rose of politics situation that I couldn't believe he was talking about openly in front of a journalist and bragging about with his friends.

DETROW: And when it comes to Sean and specifically his gambling habit on the political races he's working on, you make this point at the end of the book that you can get away with a lot when you're right - swagger, loose lips, an ostentatious gambling habit. But that changes very quickly when you're suddenly not seen as the up-and-comer or the winner or somebody that people want to be around and associate with. And it's interesting to me how quickly that happens. It seems like suddenly, on a dime, his gambling went from a joke among a lot of Democratic operatives to, well, we can't be associated with this guy because of this.

TERRIS: Yeah. I mean, for a while, he was like a wunderkind, right? And when you're a wunderkind and you are getting bigger clients and your polls are helping the Democratic cause and you've created this tool that your team appreciates, people think of him as, oh, well, you know, he's got eccentricities, right? He - maybe he gambles on politics. Maybe he encourages his staff to gamble. Maybe he even Venmos them money and calls it DFP stimmies (ph) - for Data for Progress stimulus that he gives to his staff so they will bet on politics. Maybe he does all that sort of stuff, but he's helping us win, and he's a team player. We're a team, so we support him, right? There's - Washington is, like, kind of a funny place sometimes, right? I hope that people can read it as a romp but also read it, understand why things are the way they are and realize that, you know what? Things are twisted there, and this is why.

DETROW: Let's talk about another person who probably could not exist, at least not in this blatant form, before Donald Trump came to Washington. And that's Robert Stryk, who finds a place for himself as somebody with loose ties to Trump world, somebody who can get people in with Trump world. And he finds himself creating this career for himself as a lobbyist to foreign governments, often unsavory foreign governments.

TERRIS: I've been profiling kind of oddball characters for a long time, and I've never met anyone quite like Robert Stryk.

DETROW: And reading about his story, it seemed to me on one hand, this is something that seems brand new and unusual - right? - just this one person striking up deals with increasingly controversial countries for increasingly controversial topics and just trading in on the fact that he has some loose ties to Trump world. But on the other hand, isn't he really doing what's been done all along, but he's just a little more blatant about it? He has this quote to you at the end, once Biden has become president and his business model has dried up, where he says, "I only got a four-year crack at it. I want another four-year crack at it. I deserve it. I earned it. I'm still here today. Those bleep-bleep-bleep got 40 years to do it and bleeped this country up. I want four more years." Doesn't he kind of have a point there?

TERRIS: Yeah. First of all, there's a lot of bleeping when you talk to Robert Stryk. Yeah, and he does sort of have a point. I mean, the point of this book was to look at the years after Donald Trump, right? Donald Trump came. The book is called "The Big Break," right? And it's called that because the country went through a big break. This is what - you know, what happened when Trump shook up the country's psyche for four years and longer, when, a lot of ways, Washington was revealed to be what it was because of Trump. He showed kind of this griftiness (ph) and this obsession with showmanship that was always there. But you could see it even more clearly once he was president.

And after the fact, once Biden comes in, a lot of the rules of how to play the game revert back to where they were, to a degree. I think Trump has changed Washington in a lot of ways. But for somebody like Stryk, who was able to take advantage of the Trump moment, it wasn't really clear how he could take advantage of the Biden moment the same way. He'd gotten in the door, but now people weren't necessarily as interested in talking to him because there was a president who did things in a more, quote-unquote, "normal" way than when Trump was around.

DETROW: I want to ask you a couple questions about your writing process and your reporting process because you have this book. But I also think for years, the profiles you've written for The Washington Post have been some of the most insightful profiles about people in Washington that are out there. And with Stryk, you let the reader into something that usually is not reflected in a book or a piece, and that is how someone responds in real time to the idea of you reporting on them and profiling them. You're someone who's very skilled at getting people to open up to you. And I feel like you do write with a lot of empathy. But sometimes, because of the details you've acquired, you can write details and scenes that are just devastating. And I'm wondering how you handle this response of a person you profiled as a reporter and as a person.

TERRIS: Well, it's very difficult, honestly. I mean, when somebody trusts me with their story, that is a lot of responsibility. It's their story, not mine. But that's only the case to a degree - right? - because they also have a story they want to tell. And my job is to tell the story that I think is true. And I think somebody like Stryk appreciated that I was taking him seriously. A lot of folks didn't take him seriously. He's a strange guy. He's a cowboy-hat-wearing, you know, guy who lives out on Alibi Farm who couldn't make it work as a lobbyist for many years, went out and became a - owned a winery in Oregon, ran for the mayor of a small town in California, got basically run out of town. He's a strange guy who is not often taken seriously. I did take him seriously. But the problem with being...

DETROW: Yeah.

TERRIS: ...Taken seriously is I take it very seriously, and sometimes I'm finding things that people aren't comfortable with. I'm revealing things about people that they're not comfortable with. And it can be difficult because everyone has a story they want to tell about themselves. And that's not always the truest story.

DETROW: That's Washington Post reporter Ben Terris. His new book about Washington is called "The Big Break." Ben, thanks so much.

TERRIS: Thanks so much for having me.

(SOUNDBITE OF AND SO I WATCH YOU FROM AFAR'S "I'LL SHARE A LIFE") Transcript provided by NPR, Copyright NPR.

Brianna Scott is currently a producer at the Consider This podcast.
Tinbete Ermyas
Scott Detrow is a White House correspondent for NPR and co-hosts the NPR Politics Podcast.