In this week’s Open Tab, Australian-born, New York–based muckraker Lachlan Cartwright sat down with Substack co-founder Hamish McKenzie to walk through two decades covering media, money, and power—from The Sun and the New York Post to executive editor of the National Enquirer, where he went from breaking news to becoming an anonymous source in one of the biggest political scandals of the decade. His New York Times Magazine cover story on the catch-and-kill operation that protected Donald Trump and Harvey Weinstein took a year to write and earned him multimillion-dollar legal threats in the process. These days he runs Breaker, the twice-weekly media newsletter and podcast he founded after years of people telling him to strike out on his own—it’s tabloid flair paired with the standards of the broadsheets and, as he puts it, a healthy appetite for fun.

Hamish: You’re a newshound, a scoop-getter, a news-breaker, and a tabloid journalist of sorts.

Lachlan: Allegedly.

Hamish: Cut from the cloth of an old-school type of reporter. And that’s kind of special in today’s world, because lots of people are just random opinionators and mouthers-off.

Lachlan: I’m an old-school newshound. Some would say a muckraker. I spend a lot of time meeting and greeting and ingratiating and sourcing. I always say I’m only as good as my sources, and that’s how I get scoops—being out and about, going out into the world and finding out new information. And then coming back, standing it up, tapping it up. And as we would say, putting it in the paper, which is now a newsletter.

Hamish: You were the number two editor at the National Enquirer, and through your work there you discovered that they were essentially paying for stories so that they could kill those stories on behalf of some powerful figures: Donald Trump, Harvey Weinstein.

Lachlan: That’s correct.

Hamish: Tell me, what was it like to write that story and have it out in the world? Because it was complicated, and it involved so much personal stuff and was a big risk for your journalism career.

Lachlan: And legally a big risk, because I was under, and still am, a nondisclosure agreement. That piece was easily the hardest piece I’ve ever had to write, and it wasn’t fun to write it. It’s fun now to have written it and to talk about it. I remember being at the ASMEs, the magazine awards, and it was right around the time that the indictment had come down against Donald Trump, the hush money indictment. I saw Jake Silverstein, the editor of the Times Magazine, there. I didn’t know him. I said, “G’day, mate. I think I’ve got a cracking yarn.” And he said, “Well, let’s follow up, and we’ll meet about it.” I sit down to write it and I thought, “I can’t do this.” I was getting out old files and I was looking through text messages to re-create scenes, and, as I write about in the piece, my father died suddenly during when all of this was happening. I just thought, I can’t go over this stuff again. It’s just too much for me. And for months, I just couldn’t get anything on the page. It actually took me a year to write. Willy Staley [story editor at the New York Times] said, “Why don’t we do this in chapters? You’re good at writing your column, your newsletter. Why don’t we write this in chapters?” And I finally had the confidence knowing that I didn’t have to file 10,000 words, I just had to file a chapter at a time. I sat down and I wrote the first chapter, and I thought, “Okay, I might be able to do this.” It went through the machinery of the Times. They go [para]graph by graph and give you the colonoscopy of fact checking. They call everyone, and they re-report basically the entire piece out. But it took a year for the whole piece to come together. And it’s easily one of the proudest moments I’ve had when it did finally publish and the whole story was out there.

Hamish: Can you explain for the average person what catch-and-kill actually looks like?

Lachlan: It wasn’t a term I was familiar with when I took the gig as executive editor of the National Enquirer. The first year was run-of-the-mill tabloid fare: Jen and Ben. True-crime yarns. Not Pulitzer Prize–winning stuff. But there were yarns we broke that moved the needle.

It was towards the end of that first year where I had a tip from a very good source who calls me on a Sunday and says, “Weinstein is being questioned over a groping allegation in Tribeca, and I can get you the girl.” I immediately called [National Enquirer editor in chief] Dylan Howard and I said, “I’ve got a cracking one here.” And Dylan just immediately said, “Who’s the source?” Something tweaked in me—Why are you just immediately going to that question, as opposed to how do we get this story across the line?” And it was the next day that the Daily News broke it.

After that, Dylan came into my office and said, “We need to offer her a five-figure amount for her story.” And I was like, “We had the scoop yesterday and we didn’t need to pay her. And now you want to give her money to get her story.” And I just remember thinking, “Something’s off with this whole thing.” She doesn’t want paying. She wanted to get the story out. We had the story yesterday.

Hamish: Why did you start Breaker?

Lachlan: You were telling me for years to strike out on my own as an independent media. You were at me for years. And guess what? You were right.

Hamish: Thank you.

Lachlan: At the time, I thought you were mental when you were like, “What are you doing at legacy?” And you were the bloke who kept saying—because you’ve got to remember, The Daily Beast had a newsletter called Confider, which turned out to be an industry must-read—“Why are you doing this for these people? Strike out on your own.” And you said that to me again when I went to the Hollywood Reporter. Which you were right. I should have just gone straight from The Daily Beast and struck out on my own.

I was freelancing, writing for Vanity Fair and THR and The Ankler, and I thought, I could keep freelancing or I could try and create something myself. And getting back to my late old man, he was 41 when he started his business. And this was right around that same age. And I thought, “F**k it. I’m entrepreneurial. Here is this opportunity to go off and do it.” What’s the worst thing that can happen? I could lose my life savings.

Hamish: But people respect you more for having done it, even if it doesn’t work out. You are actually improving your career prospects by being entrepreneurial in the first place, by showing you’re willing to do something bold and taking on that risk.

Lachlan: Look, my history has been a series of punts, of gambles. Moving to London at 22 and not knowing anyone. Nailing that and going to New York. But it’s been a series of punts, and most of them have paid off in a weird kind of way. And I think the news gods respect that, if you do take a punt. And starting Breaker was a punt. It’s easily the best thing I’ve ever done. I’m working harder than I’ve ever done—16-, 18-hour days, seven days a week. But I’m creating something that, from the readers I speak to and the subscribers I interact with, is special. It’s something that if it’s not out by 8:30 p.m. on a Tuesday and Thursday, they’re texting me, “Where is it? What’s going on with Breaker?”

Hamish: You were starting this company with a partner. It didn’t work out for whatever reasons. What was that aspect of it like for you?

Lachlan: We had a business that wasn’t growing, so that was problematic for obvious reasons. I’m in a runway situation. I have a certain runway of money, and if this business isn’t growing, I’m in a pickle. And that pickle is me sleeping rough. Things got very real. We had to have a real conversation, and that conversation resulted in him going off in one direction and me having to think very carefully about: how do I propel this business forward?

I said to myself, “I have to resurrect this, and I have the fall to do it. The clock is ticking.” And I thought three things. One, you have to put on a killer event. Two, you have to relaunch the pod with a stellar lineup. And three, you have to break stories that are impactful and consequential. If you do all three, you save the business. If you don’t, we are fucked. And guess what? Fear is one hell of a motivator. The second season of the Breaker pod, we launched with Joe Scarborough, we had Tina Brown, Janice Min, Jeff Fager, David Remnick. A stellar lineup. We went from being in dive bars to two-star Michelin restaurants. I then broke a number of massive yarns, including breaking the Air Puck story—the deal that Puck was acquiring Air Mail. I broke a Murdoch yarn that CNBC picked up. And I put on one hell of a downtown media party. The New York Times came and covered it, wrote a style section piece. And that three-pronged approach saved the business. It led to a wave of subscribers, it led to a wave of revenue, and it led to me getting to Christmas and thinking, “We’re good. We’re going to hit profitability by year one.” And we were able to announce just the other week that Breaker is profitable. And mate, there was a time I didn’t think we were gonna make it. There was a time I’d wake up in the middle of the night and paint the bathroom, 50 shades of puke. [Now] I can si...