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Isabella Royo
I'm Isabella Royo, intern at LawFair, with an episode from the Lawfare archive for December 24, 202025 on December 9, Lawfare contributing editor Renee Diresta sat down on the Lawfare Podcast with Jimmy Wales, the founder of Wikipedia, to discuss the foundations of trust in digital media. The two also discussed Elon Musk's effort to develop an alternative to Wikipedia, Grokopedia, powered by xai's artificial intelligence assistant, Grok X, formerly known as Twitter, has emerged as a major power in the digital information landscape, giving its algorithmic recommendations and content moderation serious power in public and political discourse. For today's archive, I chose an episode from September 19, 2024, in which Tyler McBrien speaks with Kate Conger and Brian Mack about Elon Musk's acquisition of Twitter, the birth of the character limit, the platform's approach to content moderation, and more.
Tyler McBrien
It's the Lawfare podcast. I'm Tyler McBrien, managing editor of Lawfare, with Kate Conger and Ryan Mack, two technology reporters for the New York Times.
Ryan Mac
He has effectively destroyed Twitter. It is X now. You know, it is a completely different platform. It is a place where he's going to get into ideological fights with government regulators and a place where he'll sue advertisers if they don't advertise on his platform. You know, it's yeah, that. That's X I guess today we're talking.
Tyler McBrien
About their new book character How Elon Musk Destroyed Twitter, as well as the social media platform's troubled history of content moderation and why the billionaire wanted it all for himself. So, Kate and Ryan, you've both spent a long time on what could be collectively called the Silicon Valley beat, including at different times, the Elon Musk, Jack Dorsey Twitter beat, content moderation beats of other, other social media platforms. So I want you both to take me back to April 14, 2022, when you woke up to a forward tweet from Elon Musk's account that said, I made an offer. So, Kate, we can start with you and then, Ryan, feel free to chime in after.
Kate Conger
So this was such a funny experience for me because I was actually taking some time with the White House bureau at that point. So I had kind of stepped away from the tech beat a little bit, and I was doing a three month stint with them to cover cybersecurity in the war in Ukraine and trying to just kind of leave Twitter alone. The beat had been pretty quiet and I was like, I can take a couple months away to focus on something else. And I think I had gotten to D.C. to start this maybe two weeks before the offer. So it really threw my plans and a lot of other people's plans into chaos. And from that point on, I was kind of juggling both of those things. So it was like half of my day was Ukraine stuff and then the other half would be Twitter stuff. And I think I felt like a lot of people did. When Elon made the offer, I think resoundingly, it was, is this guy serious? Is he actually going to do it? And I really went back and forth, I think on a daily basis throughout that summer, wondering whether or not that deal was actually going to happen.
Ryan Mac
For me, it was. Yeah, it was strange because I think leading up to it, I mean, it was known he was a shareholder. He had cross this 5% threshold for disclosure with the SEC because he was acquiring these shares very quickly. He obviously didn't disclose actually at the time, at the right time, but he eventually did disclose that he was a shareholder. And the discussion around the time was like, maybe he's going to join the board, actually, maybe he will be one of several people helping to operate this company. And that was really where the discussion was at the time. So to see him then go like full bore into this acquisition was very surprising. And just so on brand that it was a tweet that kind of set it off.
Tyler McBrien
Yeah, you Both write in the introduction, you called it an unbelievable but inevitable culmination of two storylines that you both had pursued for a decade as journalists in Silicon Valley. So I like that idea of it both being unbelievable, but also inevitable. But I want to back up even further. I mean, the book tells not just the story of this unprecedented, in many ways, business deal, but also the history of Twitter's content moderation policies, these three CEOs and their histories. So I want to just hear from both of you, what was the story or stories that you set out to tell in this book, as you know, and maybe in contrast with your, as it happens, reporting of when the deal was being negotiated and then. And then completed? Kate, we can go back to you to start.
Kate Conger
Sure. I mean, I think what we really wanted to capture was Elon as sort of a person who is profoundly shaped by Twitter and then who begins to shape the company himself. You know, in tracing back his history personally, we wanted to go into how he started using the platform, how he became kind of a hardcore Twitter addict, and what really shaped his views around what online speech should look like. And in doing that, you know, we also had to tell the story of what was going on with speech on the platform that he was so addicted to and the decisions that the company had been making around speech. And I think that idea of what social media should be, what kind of conversations that we should be having there is such a potent one and something that's been so heavily debated over the last couple of years. And so we wanted to also kind of spell out these three different CEOs, their different views on that topic and how they tried to approach it.
Ryan Mac
Yeah, and I think the taking the three perspectives is very important of those CEOs. Right.
Kate Conger
We.
Ryan Mac
We start with Jack Dorsey, who we start with. We start the book kind of with his return. You know, he is someone who founded the company, created, you know, the start of the platform, and then was kind of exiled and sent away. And, you know, our start of the book is him coming back into the fold, being the CEO, running the company and just, like, hating it. You know, he just despises it. By the time he leaves, you know, he's run into the ground with all these content moderation decisions. He hates going to Washington to, you know, have to testify in front of House members and senators. You know, he just. He is not cut out for the job. And he just, like, begins to question if this should be ever have been like, a business. You know, there's also the story of Parag Agarwal this kind of idealist guy who worked at Twitter for a long time and worked his way up to the top, and it was a very surprise pick for the CEO position among employees. You know, and he kind of gets this job thinking he's going to implement so many changes and, you know, bring about efficiencies. He was going to implement layoffs. And he just gets waylaid by this, this, you know, this force of nature in Elon Musk, who, you know, is the main character of the story and is the driver of this book. But like, to understand the history of Twitter, you have to kind of take into perspective all three of their. Their stories.
Tyler McBrien
Yeah, it was really interesting contrasting the three of them because there's. There are clearly through lines between them. Also, Dorsey played this sort of. I was unaware of this almost kingmaker role in that he championed Aggrwal and then he championed Musk. And I wasn't really aware, I mean, you know, he was the CEO, but I wasn't aware then these successors that the big role that he played. So where do you see their views of Twitter and Twitter's many, many confounding problems of content moderation and revenue? Where do you see the three of them converging and where do you see them? Where do you see the big differences between their philosophies?
Kate Conger
I think the agreement between the three of them is that something has to change with the way that we moderate online content. I think all three of were really united in the idea that the way that Twitter was going about it wasn't working. And then you see them really drastically deviate on how to solve that problem. And, you know, it's funny that you mentioned Jack's sort of kingmaker role in picking the people who would succeed him at Twitter because he had become so disillusioned with it, and yet he can't quite let it go. And so there's this theme again and again of Twitter just being this kind of, I don't know, I mean, just this addictive force for these people where they just can't quite separate themselves from it.
Ryan Mac
I think one of the funniest things, though, is like, the board taking his advice. You know, he is a guy, like, by the end of his. His tenure as the CEO the second time, like, he hated the board. You know, the board didn't really like him, and yet they're listening to his advice on who, you know, should be his successor. It's just this very strange dynamic. And, you know, he was literally like, tweeting out like I hate the board. Like, it, basically, I hate the board. Like, you know, it's just like this insane infighting that you never see at these companies. And yet he still had an incredible influence, you know.
Tyler McBrien
Yeah. I found it all the more strange given this stark contradiction that really leapt out of Dorsey getting, you know, actively not only tweeting out how much he hates the board, but also being so transparent about Twitter's problems. And this, this, I think, idea that he eventually came to, that you write about several times about this, the original sin of Twitter, that it should have never been a for profit company, but rather protocol, like, like email, which, which also Agrawal shared. So I was wondering if you could expand on that. This, this connection between Agarwal and Dorsey as well as. I wanted to make sure to bring up one of my favorite anecdotes from the book, which was during one of these one team events when I believe Dorsey was still CEO and he was talking about one of his health fads that he was into called Salt Juice. And I felt like it was such a perfect micro portrait of Agrawal. So first I was wondering if one of you could tell that story and then this relationship between Agrawal and Dorsey. Sure.
Kate Conger
So the one team that you're talking about, I believe is the first ever one team. And it was when they were still doing it in San Francisco at Moscone Center. And it's when Jack is really in his meditation health era and he got really into what the employees sort of lovingly termed salt juice. And so it's this sort of little cocktail that he would drink. It's just water, I think, Himalayan salt and lemon. And, you know, Twitter would serve it in the cafeterias, in the offices and have a little label that called it salt Juice. You know, just kind of like teasing him a little bit about it, I guess. But so this one team, when he came out on stage, he had everyone kind of check under their seats and there was like a little gift bag with the salt juice ingredients so people could, you know, mix up a little salt juice and drink it during his talk. And, you know, we had heard this amazing story about Parag just kind of whipping it out and like throwing all the salt in there and taking a swig before Jack had finished walking through the instructions and telling everyone, no, it's just a pinch of salt. You know, don't go overboard. But it was just, to me, this really interesting way to show their connection and the way that Parag was really willing to align with Jack and some of the things that he wanted to do and sort of, I think, like, was a good translator for Jack, that Jack would have these sort of kind of wild ideas about how he wanted to reshape social media or things he wanted to do at the company. And then Parag would come in as one of his deputies and sort of sort out the logistics of actually making that happen and figure out how are we going to take this sort of harebrained idea and make it. Make it work, make it functional.
Ryan Mac
I think it's so strange because, like, you know, Parag was the cto, but had very few reports. I think there were like, maybe half a two dozen folks that rolled up to him. So he's kind of like in sort of this, like, ivory tower position, but was very close to Jack. Like, he, you know, they had these, like, kind of jam sessions where they talked about ideas like content moderation, and, you know, they bonded over that stuff. So, you know, it's just like this relationship that he didn't have with any other executive. Funnily enough, by the way, I was actually at the 2018 One team, actually was a speaker. There was a panelist of journalists, although I never got the salt juice, so I can't tell you what that.
Tyler McBrien
It seems like a simple enough recipe. I was tempted to.
Ryan Mac
Yeah, I think at home.
Kate Conger
You could whip it up at home, I think.
Tyler McBrien
Right. So it was interesting to read about Dorsey and Agarwal's mind meld on a few things, like this idea of there should be freedom of speech, but not freedom of reach, which they had, you know, come to. To, or they, you know, they'd been taken by. And the kernel of which eventually became blue sky, if I'm not mistaken. But if. If Dorsey kind of represented this idea of we need to actually tear it all down and rebuild something different. Musk, it seemed like, was coveting Twitter almost in a I can fix her kind of way, despite all of these, you know, glaring problems. So I wonder if you could explain, you know, in your. In your view, why. Why was Musk so obsessed with Twitter, not just as a user, but also why did he want to, you know, buy it?
Ryan Mac
I. It's. It's one of the biggest questions of the book. And, you know, I think it's as simple as him loving the platform. You know, we trace his. His usage of it, and in 2009, ish.2010. Ish, like, he didn't really get it. He didn't. He didn't. He wasn't like a. You know, there were people in the early Days of Twitter that would tweet, like, you know, today I'm eating sushi and tonight I'm going like, I'm going to bed now. Good night. You know, he wasn't one of those people, and he didn't really understand the utility of the platform. Like, he would post, you know, pics of like, him going to the skating rink with his kids or like hanging out with Kanye. And he even had a tweet where he's like, I don't know if this is the right platform for me and my message. But he just, over time gets more and more used to it, uses it more, and like, begins to understand it's a platform for him to connect with his fans and his customers and as well as to push back on the media. You know, he was someone who was obsessed with how his story was told and would like, use Twitter to combat some random blogger in Belgium who, like, made fun of Tesla or, you know, Bloomberg Businessweek for getting his what he ate for breakfast wrong in a story. You know, that was just what he came to use it as. And he, you know, understood that this was like his way of being real with an audience and be building a fan base essentially. And, you know, Fast forward to 2022. You know, he is one of the most, like, heaviest users. He is. He's just addicted to the platform. He's spending hours on it every day. He's tweeting dozens of times a day, and he is wealthier than ever. Tesla's stock is through the roof. It's at all time highs and in the way that billionaires buy yachts or sports teams. I think he just coveted this company and forced through this transaction that kind of, in some ways is unprecedented of one person buying a single company to own and covet and call as precious, I guess.
Tyler McBrien
Yeah. And I wonder if we could pause here, maybe. Kate, you could describe the importance of Twitter as a platform. You know, it doesn't rank at the top of users, obviously. It's, you know, business models have been lackluster for the most part, and yet it plays this outsize importance in culture and politics, journalism. So I wonder if you could bring in that part of the aspect of Twitter's importance as a platform, musk or no? Musk.
Kate Conger
Yeah, sure. I mean, I think a lot of people talk about Twitter as being the global town square and it's sort of a hokey phrase, but I think there is some resonance to it and that's why people always come back to that. There's something about Twitter that has an immediacy that I think is really important for public discourse. And, you know, you, when you look at Twitter in comparison to other social media platforms, I think one of the things that has always made it really stand out is the fact that Twitter is like, stuck very consistently to offering a chronological timeline. They do have an algorithmic option, obviously you can switch back and forth. But other social media platforms are purely algorithmic. And when there's something happening in a moment that everyone wants to discuss, the power of that chronology becomes very significant. Right. Because you can quickly hop onto this platform, everyone's talking about the thing that you want to talk about, and you can jump right into that conversation. And so there's just this, like, this raw power and immediacy that happens there that has made it, I think, the top platform for social and political discourse. Obviously, there are other platforms that have far more users, make far more money, but when you have an urgent thing on your mind that you need to talk about, Twitter has always been the destination for that.
Tyler McBrien
And as we're still talking about what sets Twitter apart, another thing that sets Twitter apart from other platforms in some ways is its content moderation practices and policies. So I wonder if we could just trace the evolution of that, because it's laid out really well throughout the book. I mean, you touch on just about every big content moderation inflection point in Twitter's history. Ferguson, Gamergate, Covid, the Hunter Biden laptop, January 6, the Trump ban, Russia's full scale invasion. The list goes on. There is a through line that to a certain extent, the tweets must flow as I think was an early Jack Dorsey mantra. But of course there have been many twists and turns. So how do you wrap your head around Twitter's philosophy of content moderation through the three successive CEOs? I know there's so many details within that question, but I don't know if you have a big picture narrative in your head.
Kate Conger
Yeah, I mean, I think early on, the view that Twitter had of what online speech should be was sort of shaped a lot by the cyberpunk ethos of some of the founders. And for me, and I think a lot of other people in that generation who grew up in that phase of the Internet, that was something that was very compelling about the early Internet. Like you could do whatever you wanted, you could say whatever you wanted, you could connect with whomever. It was this sort of anarchic open space. And, you know, I think Jack and the other Twitter founders were really attracted to that and they wanted to Bring that ethos into Twitter and not lose sight of that. And you see that as well, I think, in the way that Jack talks about wishing he had made Twitter a protocol. Right. There's something there that is compelling about the values that shaped early Internet and the idea of being able to interchange information freely between platforms without building these kinds of walled gardens that we have online today. So I think that kind of like cyberpunk open ethos was a really big part of early Twitter, and it shaped the idea, like you said, of the tweets must flow. Everyone needs to be able to say whatever they want.
Ryan Mac
Free. Free speech wing of the free speech party, right?
Kate Conger
Yeah. And it was really through some of these key moments that played out on Twitter that the company started to learn this might not work. You know, and we talk about in the book some of the studies that they did to kind of discover that having this kind of hostile platform actually made fewer people comfortable to speak. And they started to move towards this idea of, you know, wanting to elevate the voices of the many instead of the voices of the few and thinking about, okay, if. If this is a platform that's known for harassment and for abuse, there's going to be a couple of really loud voices that dominate. But people who are worried about, you know, receiving online abuse or harassment are going to be too nervous to engage with the platform. And so if we want to really enable speech for the broadest amount of people, we need to make it safe enough that people are comfortable to engage. And so that was kind of the beginning phase of Twitter starting to think about content moderation and introducing anti harassment and anti bullying policies. And then you go from there into, obviously 2016. The way Russian interference on social media platforms really kind of set off alarm bells throughout the industry. And I think made a lot of platforms mature their content moderation policies and systems to think about what, what intentional wide scale manipulation of these platforms might look like and how to counteract that. And so you kind of get into this big, bigger swell of content moderation throughout the industry, right? And then, you know, you start to see some of the backlash to that. The Hunter Biden laptop decision, for instance, I think is a big radicalizing moment for Jack where, you know, Twitter chose to temporarily limit that New York Post story from being shared. And, you know, Jack almost immediately regrets it and comes out publicly kind of throwing his content moderation team under the bus and saying, this was a bad decision, we should never have done it. And then you kind of go from there into Jack and Parag trying to figure out, okay, if we want to allow more types of content on this platform and not get trapped in this binary decision of take it up, leave it down, take it up, leave it down, how do we do that in a principled way? And that was really the mission, I think, of Parag's tenure as CEO was to figure out how to open up the platform and allow more types of speech without losing all of the principles of protecting users. And we talk about again, how he planned this project basically up until he had to run out of the building when Elon took over and never really got to see it to fruition. So then from there we go into the Twitter X that we know today, where Elon, I think, has shared that same mission of wanting more content to be on the platform, but hasn't shared the ideals of wanting to do it in a principled way, wanting to do it in a structured way, and wanting to do it in a way that protects many voices.
Ryan Mac
I think I would add in there the role of advertising as well. Twitter built a company around the idea that people will make content for free. We will get brands to then buy ads on our platform, and, you know, your typical ad revenue, you know, based model. And advertisers in the content moderation discussion don't want to see kind of a free for all on the platform. You know, they want to. They want to make sure that their stuff is brand safe, their stuff is next to brand safe content. And so, you know, that definitely played into the thinking throughout the years as well of Twitter. And it also gets back to, you know, Dorsey's original sin here was, you know, creating a company that was reliant on advertising and could be beholden to advertisers, essentially. And we're now seeing that play out now with Elon, you know, essentially suing advertisers for. For not advertising on. On X, which is just. Just an insane move.
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Tyler McBrien
The other aspect of the content moderation story I wanted to pick up was the human labor element both internally in Twitter, the trust and safety teams and gutting them or building them up, and then also the contractors of the droves of contractors who have to sift through sometimes extremely traumatic material. Can you bring in that aspect? There are some other characters in the book who played big roles in Twitter's history, like Ul Roth. Yeah, can you bring in also this labor question of other workers who are dealing with the content moderation problem.
Kate Conger
Yeah, I mean, I think that was one of the concerns that Jack and Parag both shared was that as Twitter grew, they felt like they had to have this ever expanding workforce of content moderators. And like you said, a lot of that labor is contract labor and people end up being paid fairly little to look at incredibly traumatic content as a service grows and matures. You just have to keep adding to that. There's really no limit if you have a lot of people posting, there's no limit to how many people you might need to moderate that content. And it was something that I think they were really worried about and wanted to find other solutions for. But I think that this, this work in general of moderating content online, it's very traumatic for both those frontline workers and for the people who are setting these policies at these companies. And I think that's a story we tried to get into a little bit as well and show the impact that working on these problems, setting these policies and making these decisions has had on the people who had to do that work and sort of the trauma of that that follows them after they end up leaving these jobs.
Tyler McBrien
I want to turn now to the deal itself and how it went down the book. I was amazed by how deeply reported it was and how you were able to both tell this incredibly nuanced, detail oriented story of backroom deals, sometimes complex financial transactions, but then also tell this parallel story about how it was also a snap decision sort of made on a whim, that both things are true. So without getting into too much detail, because there is so much in the book that is, like I said, really engaging and almost reminded me of the balance of detail and accessibility that you find in a succession or an industry or something. But without getting into too much detail, how did Musk pull it off? How was he able to buy Twitter?
Ryan Mac
I think we need to calculate for, or at least discuss that he didn't want to buy Twitter too. You know, he makes his offer, he realizes that his offer is way too high, you know, then starts, then backs out or attempts to back out and says, you know, he starts to try and find excuses. He says there's a bot problem, for example, Twitter sues him to enforce the purchase agreement and they do this dance and, you know, within, you know, eight months, the. The deal is signed. And, you know, that is, that is just insane. I don't know. It's just like I've never seen another acquisition play out like that. But how did he do it? I don't know. I think there is a lot of shooting from the hip. You know, there is a lot of him telling his lawyers and bankers he wants it to be this way, and they have to kind of backfill his request. What was really helpful is the lawsuit itself kind of showed the letters being sent back and forth, the text messages that we were able to kind of just tell, sometimes hour by hour, descriptions of what was going on. He would say something on text, and then a letter would be sent to Twitter arguing why they had the right to back out of the deal, for example. So that. That kind of gave us this rich kind of sandbox to plan with all the reporting that we had and as well as, like, you know, talking to dozens of people involved with the deal.
Kate Conger
Yeah, I mean, I think that the thing that I find so fascinating about Elon Musk and unique in the tech industry is his need to handle all of his business himself. You know, any other CEO of his stature has, like, a whole team that's kind of assisting them with these things. And it's so fascinating because, you know, Elon just really handles it all on his own. And so you see him, you know, as soon as he decides to buy the company, starts running through his Rolodex and texting all his friends, asking them to invest. And it comes together in this very casual, informal sort of way. You know, even up to the close of the deal. Right. He had kind of, as Ryan mentioned, gone back and forth about whether or not he wanted to buy the company, suddenly decided that he did, and then had to round up all of that money at the very last minute from the people who had promised it to him. And, you know, it comes down to the wire at the close of the deal where, you know, he's still short a couple million dollars and is hitting people up trying to figure out how to get that money. So, yeah, I mean, how did he do it? I just. Your force of will, I think, is the only way to explain that.
Ryan Mac
I would also add to that there is, like, a view of the world he has, which is to boil down things to first principles. And if he's told why he can't do something or he can't do something, he's going to ask why. And so, for example, he wants the deal to close very quickly when they're signing that first purchase agreement. And he doesn't understand why it would take so long. Why does it take months for bankers and lawyers to. To, you know, go over every detail, do due Diligence. Why can't it just be done now? If he forces his lawyers to do the deal, I think in like a 48 hour period where they sign the purchase agreements through a weekend, you know, by Monday, he has the announcement and he makes that tweet, you know, I made an offer. But like, you know, that really screwed him in a lot of ways. Like he didn't do the due diligence that he would have done to understand Twitter's business and how the war in Ukraine would affect advertising and etc. It was just really rushed and ill advised and in part because he just doesn't take advice from anyone. He thinks his way is the best way and his gut feeling and gut instinct is the way to go about things. And either you get on board and you work with him to do that, or you, you know, you go away and you don't, you're not part of his, his circle. So, yeah, I mean, that's, that's kind of the best way in understanding why the deal proceeded in the way it did.
Tyler McBrien
Yeah, I think this compulsion toward total control came through a lot. If I'm not mistaken, one of the original catalysts maybe of the, of his decision to make an initial offer came only 24 hours after he joined the board. And he was just had so many frustrations about the limitations of, you know, one of 10 members of the board, which is, you know, already, I'm sure, a very powerful position.
Ryan Mac
I would say, you know, he. This is not a man who joins boards, right? This is not a man who wants to be a one voice among 10. It's his voice, right? He is, he is the king, the God, you know, the, the only one. And it's, it, this, this kind of hero centering of himself plays out through his whole life. You know, he is the man who's going to get us to Mars. He is the man who is going to electrify, you know, vehicles. And he, this is how he has become so successful. I mean, who's to argue with a net worth of $250 billion? And so when he joins the board, you know, he realizes what does it mean? I have to like, attend meetings and, you know, give advice and I can't run this company. Like, I see this problem on my Twitter feed. How come I can't address it immediately? This sucks. I have to go through consensus and he just gets in a fight immediately with Parag over a small issue and just is like, screw this, I'm not going to be on the board. I'm going to buy the company. And it's kind of through this fit of rage that we see this transaction just kind of spark into life.
Tyler McBrien
Yeah, I thought it was an interesting detail contrasting the makeup of Twitter's board with, I think it was either Tesla or SpaceX's, which consisted of, I think half the members. One of them was his brother. He retained all the control, which doesn't sound very much like a board to me. In other senses.
Ryan Mac
Yeah, both companies, I mean, Tesla less so now that it's public company. But Kimbal Musk, his brother, is on there, a lot of his close friends, some of his inner circle people that have believed him in him for years and have gotten rich alongside with him. And that's coming, you know, it's causing corporate governance questions to this day.
Kate Conger
You know, it doesn't sound like much of a board to our courts either.
Ryan Mac
And how do you hold him accountable? Like this is, you know, and these people have every incentive to keep him in power. Like they've become very rich off of him. You know, Tesla's chairwoman is extremely wealthy off her association with the company. So it's like, why keep this person in check?
Tyler McBrien
Yeah. In fact, I remember one of the criticisms that Elon raised while his brief stint on the board was that his fellow board members didn't have enough stake in the company and therefore didn't have the company's best interests in mind. Which was an interesting inversion. But I will say, before this next question, I was very tempted to turn this entire conversation into sort of armchair, you know, psychologizing of this incredibly interesting man. I'll just put it that way. You know, at the risk of turning this into that, how do you reconcile, you know, Elon, the self mythologizing man who has built these huge companies with this other side of him, thin skinned, paranoid, impulsive, you know, Is the answer just that, you know, he contains multitudes or I don't know how you've. After having followed him for so long and reported on him for so deeply, how do you think of these contradictions?
Kate Conger
You know, I try to think of it from Elon's own lens because I think that's just, I don't know, I think that's probably the best way to understand his own self conception. And he often talks about his origin story and his experiences with abuse as a child. And I think that some of the traits that we often see in people who experience child abuse, you know, it's something that makes you feel like you have to earn love and support rather than Just be given it. And that you have to push yourself very hard to get that recognition and to get that acknowledgement. And I think Elon has talked about how much that's shaped him and the way he interacts with the world. That he wants to push himself to extremes in order to succeed, that he wants to push other people and drive them in that same way. And that can often bring him to be, I think, quite cruel to the people around him. But that's sort of how he, I think, gets all of those ideas and those concepts of himself together in a room to be someone who on the one hand is incredibly successful, incredibly powerful, and someone who's also very impulsive and struggles with some of his human interactions with other people.
Tyler McBrien
It's very well put. And I want to now turn, as we're reaching the end of the conversation, to the hallmarks of Musk is X. As it stands now, you both mention in the book that this is a story that's still happening. You write, musk's conquest is not over. So this is something that continues to unfold. You know, things have happened since you published the book. I believe that, you know, X being banned in Brazil has happened after you wrote the book. What are the hallmarks of Musk's X as it stands? What do you see as the major features?
Ryan Mac
I mean, X. X is created in his own image. It is exactly what he wants it to be. It is, you know, algorithmically boosting his own tweets to the for you page more so than ever. It is, you know, he is a place where he is the most followed account. You know, I think he's nearing 200 million followers at this point. He's 197 million. It is a place where you can buy engagement. It is, you know, as a, you can purchase a blue check mark, you can start saying whatever you want and you get boosted in the replies because, you know, he viewed the media as our, you know, members of the media as, you know, untrustworthy and undeserving of those blue badges. And he kind of saw, you know, the selling of them as the way to democratize them. Well, that's attracted folks that believe in his mission. And it's kind of like a self selecting group of people that you now see at the top of your replies are boosted in the for you page. So he has, you know, our book is called, you know, the subtitle of our book is about how Elon Musk destroyed Twitter. He has effectively destroyed Twitter. It is X now, you know, it is it is a completely different platform. It is a place where he's going to get into ideological fights with government regulators and a place where he'll sue advertisers if they don't advertise on his platform. You know, it's. Yeah, that, that's X, I guess I.
Tyler McBrien
Want to also ask, by the time this airs, the book will have come out. But of course, you know, you stop writing a book, you know, months at least before it comes out. I'm curious how well you think it has aged so far, given that this is such a fast moving story and how it will continue to age.
Kate Conger
I mean, this was a source of incredible anxiety for me. I think we talked for all of us, for all of us. We talked to so many other authors about the book writing process because this is our first book and we wanted to know what to expect. And everyone told us, oh, the writing is really hard. It's so grueling, you lose your mind. And maybe this is like my red flag. But I enjoyed the writing of the book. I thought that part was fun. But the anxiety of having to stop and wait for a couple of months for this thing to print and be published was awful because we are dealing with a subject who makes and breaks news every single day. That being said, I think we've gotten very, very lucky so far. You know, we made the decision to end the story with Elon and Trump kind of coming together and aligning. And I think that, that in hindsight has worked out very well. As you know, Elon has become nothing but more vocal in his support of Trump since we stopped writing. And, you know, I think that we're really going to see Elon sort of flex the muscle of X going into this election and try to really use the platform for its maximum political influence.
Ryan Mac
I mean, we've, we've seen that, you know, he held it an X space the other day where he interviewed Trump, you know, for two and a half hours, and they both rambled on about their, you know, pet peeves or whatever political issues. You know, he is in the tank for one political candidate, right? Like, it's pretty clear there is one campaign that is spending a lot of money in on X ads. You know, so if we were to keep this book going, I think there would be probably like 300 more pages of, like, things that he has done this week, you know, conspiracy theories that he has engaged with, you know, countries that he's been kicked out of. But I think we had a pretty clean break. And I'm, I'm glad because I did. I do think it ages pretty well. Like it continues to go in that kind of down that rabbit hole.
Kate Conger
Well, and you talked about how it might age into the future and you know, who knows. But when we set about to write this, we really wanted it to be something that was very character driven and would be interesting to read even well into the aftermath of this transaction. I think it's a very historic deal. It's one that deserves to be documented in depth. But ultimately I hope that this book will stand on the strength of the characters and sort of the the human portraits that we've brought to play here.
Tyler McBrien
Well, I couldn't agree more. I think every musk and X headline I've seen since I finished the book has only added color to this portrait that you painted. So congratulations on an excellent book and thanks so much for joining me.
Kate Conger
Kate and Ryan, thank you so much.
Ryan Mac
Thank you.
Kate Conger
It was really fun.
Tyler McBrien
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Episode: Lawfare Archive: ‘How Elon Musk Destroyed Twitter’ with Kate Conger and Ryan Mac
Host: Tyler McBrien, Managing Editor, Lawfare
Guests: Kate Conger and Ryan Mac (NYT Tech Reporters, Authors of ‘How Elon Musk Destroyed Twitter’)
Date: December 24, 2025 (originally recorded September 19, 2024)
This episode offers an in-depth discussion with Kate Conger and Ryan Mac, two seasoned technology journalists, about their book, How Elon Musk Destroyed Twitter. The conversation explores Musk’s tumultuous acquisition of Twitter, the platform’s fraught history with content moderation, the contrasting philosophies of its three most recent CEOs, and the consequences of the platform’s transformation into "X." Throughout, Tyler McBrien guides the authors through vivid anecdotes, keen analysis, and reflections on the real-time nature of this ongoing story.
“When Elon made the offer, I think resoundingly, it was, is this guy serious? Is he actually going to do it?” (03:40 – Kate Conger)
“...to see him then go full bore into this acquisition was very surprising. And just so on brand that it was a tweet that kind of set it off.“ (04:56 – Ryan Mac)
Three CEOs, Three Philosophies:
Addictive Nature of Twitter:
“Twitter just being this kind of...addictive force for these people where they just can't quite separate themselves from it.” (10:01 – Kate Conger)
The "Salt Juice" Anecdote:
“...Parag just kind of whipping it out and like throwing all the salt in there and taking a swig before Jack had finished...” (12:26 – Kate Conger)
“...in the way that billionaires buy yachts or sports teams. I think he just coveted this company...” (15:49 – Ryan Mac)
“...that immediacy that I think is really important for public discourse...just this raw power...” (18:26 – Kate Conger)
Philosophical Shifts:
“Twitter chose to temporarily limit that New York Post story...Jack almost immediately regrets it and comes out...saying, this was a bad decision, we should never have done it.” (22:04–24:06 – Kate Conger)
Musk's Different Approach:
“Elon...hasn't shared the ideals of wanting to do it in a principled way...and wanting to do it in a way that protects many voices.” (24:42 – Kate Conger)
Advertising’s Role:
“You just have to keep adding to that...it's very traumatic for both those frontline workers and the people who are setting these policies.” (33:39 – Kate Conger)
“He just doesn’t take advice from anyone. He thinks his way is the best way and his gut feeling and gut instinct is the way to go about things.” (38:30 – Ryan Mac)
Autocratic Control:
“This is not a man who wants to be a one voice among ten. It’s his voice, right? He is the king, the God, the only one.” (40:25 – Ryan Mac)
Personality Analysis:
“I think Elon has talked about how much that's shaped him...he wants to push himself to extremes in order to succeed, that he wants to push other people...” (43:34 – Kate Conger)
“He has effectively destroyed Twitter. It is X now...It is a completely different platform.” (45:41 – Ryan Mac)
“I think it's a very historic deal. It's one that deserves to be documented in depth...I hope that this book will stand on the strength of the characters and sort of the human portraits...” (49:23 – Kate Conger)
On the Twitter purchase:
“He just coveted this company and forced through this transaction that kind of, in some ways is unprecedented of one person buying a single company to own and covet and call as precious, I guess.” — Ryan Mac (15:49)
On Twitter’s addictiveness for its leaders:
“There’s this theme again and again of Twitter just being this kind of, I don’t know, I mean, just this addictive force for these people where they just can’t quite separate themselves from it.” — Kate Conger (10:01)
On content moderation’s impossible balance:
“You need to make it safe enough that people are comfortable to engage...that was kind of the beginning phase of Twitter starting to think about content moderation and introducing anti harassment and anti bullying policies.” — Kate Conger (22:04)
On Musk’s autocratic approach:
“This is not a man who joins boards, right? This is not a man who wants to be a one voice among ten. It's his voice, right? He is, he is the king, the God, you know, the, the only one.” — Ryan Mac (40:25)
On the transformation of Twitter:
“He has effectively destroyed Twitter. It is X now. It is a completely different platform.” — Ryan Mac (45:41)
Musk's Twitter takeover was impulsive, personal, and transformative.
Driven by ego and personal values, Musk changed the platform’s mission, rules, and culture—often autocratically and sometimes recklessly.
Twitter has always wrestled with its identity and responsibilities.
Leaders struggled (and failed) to reconcile ideals of open discourse with real-world harms and business needs.
The transformation into "X" is a paradigm shift:
What was once a “global town square” is now a personality-driven platform reflecting Musk’s unique philosophy and political inclinations.
This story is unfinished.
The consequences of Musk’s changes—for free speech, online safety, business models, and political impact—are still unfolding.
For anyone seeking to understand not just “how” but “why” Twitter became X, and why this story matters for democracy, media, and tech, this episode is a vital listen (or, in this case, a vital read).