Few writers possess the talent and range of Patrick Radden Keefe, and it is also fair to say that even fewer can outmatch his productivity. He is best known for his best-selling books on the Sackler family (Empire of Pain) and the Irish Troubles (Say Nothing), but he has also written books on people-smugglers (The Snakehead) and government eavesdropping (Chatter). Now comes the publication of Rogues: True Stories of Grifters, Killers, Rebels and Crooks, a collection of his magazine pieces for The New Yorker. It is a marvel of a book, showcasing not just Keefe’s diverse interests but also his skill at marrying investigative journalism with terrific storytelling. Keefe lives in New York.

JIM KELLY: The range of subjects in your new collection is both startling and impressive, from a vintage-wine con man to El Chapo, to a global arms broker, to Mark Burnett, the creator of The Apprentice, who turned Donald Trump from a mediocre real-estate developer into America’s top business boss and thus paved his way to the White House. Is there a common thread here among these characters that attracted them to you?

PATRICK RADDEN KEEFE: I’ve always been drawn to stories about big personalities: people who skirt the law or bend it to their will; rascals, hustlers, colorful characters. I’m also really fascinated by that gray zone where the licit and illicit worlds intermingle.

J.K.: The book’s final profile, originally published in 2017, is of Anthony Bourdain, the globe-trotting chef turned writer and TV star. You brilliantly capture his manic work ethic and his freewheeling approach to his TV series, which was, “I travel around the world, eat a lot of shit, and basically do whatever the fuck I want.” But what he appeared to be is not who he was, which was, as you say in your memorable phrase, “Apollo in drag as Dionysus.” What was it like to hang around him, and what went through your mind when you learned he had killed himself a year later?

P.R.K.: Traveling with Tony was one of the great highlights of my professional life. I spent a year hanging out with him, sharing meals, talking about his life. I ended up recording nearly 30 hours of conversations. Halfway through, I remember calling my New Yorker editor, Daniel Zalewski, and saying, “This is getting way darker than I anticipated.” But of course I didn’t know the half of it. His death was a huge loss. It’s a measure of the man’s vitality that he’s been dead four years and I still think about him all the time.

Anthony Bourdain and Patrick Radden Keefe at a talk in 2017.

J.K.: One of the most striking profiles in your book is of Amy Bishop, a neurobiologist at the University of Alabama in Huntsville recently denied tenure, who shot six people at a routine faculty meeting in 2010, killing three of them. Her background did not seem that of a mass killer; she had a doctorate from Harvard, she had a husband, she was the mother of four, she had no criminal record and no history of drug use. Yet, as the reader discovers, Bishop had shot and killed her brother in 1986, a tragedy ruled as an accident at the time. How you reconstruct her life is a narrative tour de force, relying on interviews with dozens of people, including Amy’s parents and Amy herself. How do you go about that most delicate of tasks, gaining the trust of members of a troubled family who have no reason to talk with you?

P.R.K.: Getting to know the Bishops was one of the more moving and profound experiences I’ve had as a journalist. Initially, they wouldn’t talk with me, but I kept going back to Braintree (the Massachusetts town where Amy grew up) and talking to more and more people who knew the family, and I guess word got back to them, and eventually they got in touch. The challenge—and it’s something I’ve encountered since on other stories—was that they were quite deep in denial. So I had to be as sensitive as I could be to that in my reporting, but then, in the telling of the story, I had to be somewhat bloodless. If I’m pulling punches and omitting important details out of a sense of compassion, I’m not doing my job.

J.K.: Come to think of it, the way families work is a major theme of yours, whether it be the Bishops or the McConville family, in your book about Northern Ireland, or, of course, the Sacklers, in Empire of Pain. Have you thought about why you are so drawn to family stories? Do you subscribe to the poet Philip Larkin’s line “They fuck you up, your mum and dad”?

P.R.K.: Ha! I love that poem, and in dark moments have occasionally invoked it, but I can’t really account for what it is about the bonds of family that so intrigues me. My own family life has been pretty happy, as these things go. I’ve noticed, though, that I’m particularly drawn to sibling relationships: Amy Bishop, who kills her brother Seth; Astrid Holleeder, who turns state’s evidence on the biggest gangster in Amsterdam, her brother Wim; Ken Dornstein, who spends three decades trying to track down the terrorists who killed his brother. (All of these characters feature in Rogues.)

J.K.: I am sure your mum and dad raised you well, and someone must have touted the value of education, since you have degrees from Columbia, Harvard, Cambridge, and the London School of Economics. You fell in love with writing by reading The New Yorker in junior high school, long before, as you write in your book, “long form” became the description of the stories you yearned to write. Are there two or three writers who you especially admired back then?

P.R.K.: Freud would have called it the narcissism of minor differences for me to point out that my law degree was not from Harvard but from Yale. The list of early influences is long, but the first time I remember reading a New Yorker article and then taking it apart, really thinking about its construction and wondering if I could ever make such a thing, was a 1995 piece about the O. J. Simpson verdict by Henry Louis Gates, called “Thirteen Ways of Looking at a Black Man.”

J.K.: You seem equally comfortable doing archival research and interviewing people. Which is more enjoyable for you? You also have been eloquent about the need to dig deeper than what is available on the Internet, since so much documentation has not been digitalized. When do you know it is time to stop digging and start writing?

P.R.K.: This is my perennial problem: I love reporting, and when I’m really stuck in on a project, I don’t notice the time going by. But I’ve got rent to pay and mouths to feed, so I’ve had to try and be more efficient. What this means in practice is that I start outlining early, and that creates certain narrative guardrails that can prevent the research from proliferating indefinitely. But yeah, it’s a problem. When I was writing my last book, I spent three days working my way through 30 boxes of legal documents that an attorney had volunteered to share with me, and not a single item from those boxes ended up in the book.

J.K.: All writers have routines, and I am very much interested in yours. Favorite time of day and place to write? Do you set a daily word goal? Any small tricks you have to keep you at your desk? John McPhee, when he was starting out, used to tie himself to his desk with his bathrobe belt to stay focused.

P.R.K.: I keep farmer’s hours and do all my best writing in the morning, on an empty stomach and an IV drip of espresso. When I was younger, I could write coherently at night; no more. My one big life hack of the bathrobe-belt variety is that I like to have a handful of different projects going simultaneously, so when I hit a roadblock or a period of discouragement in one, I can just focus my energies on another.

J.K.: Finally, a question about your best-known work, Empire of Pain. It is an infuriating book to read, but you never let anger overcome the narrative. For me, a fundamental mystery is why a family that tried so hard to downplay their connection to Purdue Pharma plastered the Sackler family name on so many college buildings and museum galleries. They could have given the money anonymously. How does their behavior square with what you discovered Isaac Sackler, a grocer, told his three sons in the 1930s?

P.R.K.: One thing I couldn’t understand was why generations of the Sackler family were so fixated on emblazoning their name on elite institutions. Then I discovered this quote from Isaac Sackler, the original patriarch, at the height of the Depression. He told his sons that he had lost everything, so he had nothing to give them—except his good name. I realized that this fetishistic devotion to the family name was an abiding trait, one which sprung from that moment. As the name comes down from so many institutions—the Met, the Guggenheim, the British Museum—it is fascinating to wonder what Isaac might have thought of the toxic legacy his descendants created. Often when you do this kind of writing, you feel like you’re howling in the wind. But that’s an irony I can savor.

Patrick Radden Keefe’s Rogues: True Stories of Grifters, Killers, Rebels and Crooks will be published on June 28 by Doubleday

Jim Kelly is the Books Editor for Air Mail