When investigative journalism is as considerable as it is at The New York Times, deeply buried skeletons are routinely dug up, even if reporters don’t always know what they’re getting into, or for how long.

In Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success, Susanne Craig and Russ Buettner, investigative reporters at The Times, set out from their nearly decade-long examination of former President Donald J. Trump’s finances. That foundational work, which won a Pulitzer Prize in 2019, forms the basis for a volume that sifts painstakingly through critical eras of Trump’s past. Craig and Buettner’s fresh reporting turns over a wealth of untold anecdotes that unfurl like a generational family crime drama. The reader is left awash in both new insight and staggering hindsight.

Perfectly timed ahead of the U.S. election on Nov. 5, Lucky Loser succeeds where political books often fall short: It’s a definitive work about a president, and it’s exceptionally fun to read. The sweeping and entertaining narrative, driven by meticulous journalism, opens with a young Fred Trump, Donald’s father, and ends on the steps of the White House. With the most consequential American election in a century less than three weeks away, it feels especially urgent.

In a recent conversation with Zoomer, Buettner and Craig, who is Canadian and grew up in Calgary, talked about investigative reporting, how a fortunate son became a lucky loser, uncovering the origins of his fondness for ALL CAPS, and what they’re reading now that they aren’t reading about Trump.

Shawna Richer: Political books don’t always have titles that leap off the shelf. Where did yours come from?

Russ Buettner: The massive amounts of money coming his way, the more we looked at it, was completely separate from him having any expertise in anything at all. It was really a framework for thinking about the whole thing. From the first conversation we had with our editor it was ‘Lucky Loser.’ And we stuck with that.

SR: How do you get from three pages of Trump’s tax returns in your mailbox nine years ago to this?

Susanne Craig: That’s the wonder of daily reporting and investigative work. We got the first tax returns in 2016, right before the election. Once he was president, we looked more at his wealth and the foundations of his wealth, and that led us to look at Fred Trump. We worked for 18 months on a story that showed Donald inherited hundreds of millions of dollars from his father, and tax fraud went into that. In 2020 we got decades of his corporate and personal tax returns, which led to more stories. A really rich narrative needed a book, his life was so singular.

 RB: It would have been impossible at any other newspaper in the world. Part of the secret sauce of The New York Times is being able to go down a road not always clear what will come from it and without much direction, other than trying for a long time.

SR: It’s hard to be surprised by Trump at this point. Did anything shock you?

RB: When he first starts working for his dad, he’s so different from his father, yet his father completely supports him. There’s this impression that he’s wealthy when really he’s just on his father’s arm for that entire period. In 1985, he just had a couple of projects and all of a sudden, with that flush of success, he believed he could do anything. He could run anything. He didn’t need partners and he didn’t listen to his own experts. His instinct was the best. That pattern started then and became calcified over the course of his life.

 SC: Learning that kid Donald Trump was just a jerk. He would go to the Atlantic Beach Club, and we talked to someone who remembered Donald standing on the high diving board as guests were coming in, and cannonballing off, spraying everybody. Everybody would get soaked and then Donald would deny it. He’s been that kid his whole life. This was a pattern that would drive his father crazy. It’s why he ended up at the New York Military Academy.

SR: How did his entitlement evolve?

SC: At the academy, Donald used his classmate’s jacket for senior picture day because it had more medals than his, because it made him look better. And on The Apprentice he started going around Mark Burnett, the TV producer who gave him this incredible deal where he was getting half the money that was coming into the show from product integration. Donald was cutting side deals. He was already getting hundreds of millions of dollars, but it wasn’t enough. He just couldn’t help himself. This behaviour has been going on his entire life.

 SR: Was showing how we arrived at the Trump we know today a journalistic choice?

RB: Early on, it felt like the story was going to be how he became the guy you saw in the White House. He emerged so vividly in all of these little vignettes and moments in his life.

 SC: We don’t go into the White House era, but by the time you get to the end of the book, you know the guy you’re going to meet in the White House. Even just understanding Fred, you come to understand Donald. We went down to the Library of Congress to look at some documents, and Fred Trump’s handwriting is on some of them, which we hadn’t really seen before. He’s writing when he’s angry in all caps! We found ground zero of the all caps.

  SR: Will Trump be lucky again in November?

 RB: Even our understanding of him can’t be predictive of what will happen. He’s still a very viable candidate. It’s a close race. I’m happy to be a spectator.

 SR: Canadians sometimes look at America and think, ‘Oh, that’s happening down there.’ How should they reckon with him?

 SC: With Canada, it matters a lot for trade. We’re connected, from economics to social impact. I don’t think you can underestimate what an influence America is and how the direction that it’s going affects everybody.

 RB: He pulled out of treaties. He pulled out of every agreement on climate change. We’re closely tied together in that regard. He made it acceptable to be irrational. He made the world safe for Beavis and Butthead. You don’t need to know policy. You can just say ‘they’re ugly and they’re idiots.’ That’s a huge, huge change.

 SR: What are you reading?

 SC: Long Island Compromise by Taffy Brodesser-Akner. It’s amazing. Everyone’s raving about it. And I just finished Trust by Hernan Diaz. The structure is outstanding.

RB: The last book I finished that was not about Trump was The Kingdom, the Power, and the Glory: American Evangelicals in an Age of Extremism by The Atlantic writer Tim Alberta. His observations were genius. His father was an evangelical minister and his tension is how did this happen out of this thing that was so central to my life? How did goodness become this force of ugliness?

This interview has been edited and condensed for length and clarity.

Shawna Richer is an assistant editor on The New York Times national desk.