You can read Part 1 here, Part 2 here, and Part 3 here.

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Learning to Code

Part 4: The End of Software

I started this journey annoyed about how one big tech company is shaping Washington policy with a well-financed influence machine to make tax and privacy laws more anti-consumer.

I discovered that from another corner of Silicon Valley, tech oligarchs might be offering tools that could level the playing field.

It was a good reminder that the effects of new technology are uneven.

AI’s radical democratization of intelligence has two sides. The question of whether it will replace workers dominates the discourse. The flip side gets less attention: how ordinary people can be empowered by AI.

Journalists have a long history of using new tools to supplement their reporting, especially in public policy. (Another example from ProPublica: their Nonprofit Explorer.) So instead of just writing about how Intuit deprived Americans of free tax-filing software, I figured: Why not also create the software itself?

That’s the full story behind TelosTax: I built a free, open-source, privacy-focused tax prep app that, at the very least, can bring awareness to the unsavory relationship between big tax prep and the Trump administration.

It is absurd that millions of Americans prepare their taxes with a product designed to siphon their data to sell them credit cards. But it’s even worse when the same company prevents the government from offering a similar service—absent the data mining—for free.

But by the end of this project, I realized something much bigger was at play in the collision between legacy software companies and new AI agents.

Why AI is addictive

The process of creating the app with AI was strange. I quickly learned that the tools can be addictive. I frequently got caught up piling new features onto the app just because I could: Tax Scenario Lab, Smart Expense Scanner, Audit Risk Assessment, TelosAI, obscure IRS forms, cool data visualizations. I added an external monitor to my laptop and populated it with six different instances of Claude Code to run tasks simultaneously.

I found myself yelling strange new phrases that alarmed my loved ones: “How can Claude only have a context window of 200k tokens?” (It’s now one million, thank God.) CLIs, API keys, and MCP servers became my superpowers. The pace of change was exhausting. Every tool I was using earlier this year has been significantly upgraded. New features that can completely change a project’s trajectory are released daily. In the middle of the project, Anthropic released Remote Control, which allows me to continue coding from my phone while I walk the dog.

It was not necessarily a healthy way to spend my time. The Harvard Business Review recently reported that using AI the way I was using it can lead to “AI brain fry.” I was nodding my head as I read that article.

As the weeks went by, the amount I spent on AI products ballooned—Anthropic Max, Google AI Ultra, ChatGPT Pro, Perplexity Computer. Playing models off of one another became a key part of the design process. GPT taught me how to write prompts to prevent Claude from hallucinating. Gemini was a useful skeptic of Claude’s overly ambitious pursuits.

I became adept at using a tool that sent Claude’s tax software ideas to three other AI models, which debated them and voted on the best way forward. They became Claude’s council of advisers and harsh outside critics. To find security vulnerabilities, I prompted them to think like hackers searching for bugs that will win them bounties. To test the tax engines, I told them to develop tax filer profiles with complex edge cases and obscure combinations of income, deductions, and expenses.

They were tough critics, but in the final rounds of pre-publication tests, Claude’s AI friends were quite impressed with him. GPT called the “pure-function engine architecture” the “crown jewel” of the app with “textbook clean architecture.” Gemini described the “authority chain (@authority JSDoc + YAML)” as “better than most commercial tax software.” Claude described the “privacy design with audit log” as a “genuine innovation” and a “masterclass in building trust.” Another model said that the “test suite methodology (oracle, metamorphic, fuzzing)” is “exceptional,” and the “documentation quality” actually “exceeds most commercial projects.” The “declarative wizard step conditions” were hailed as “brilliant.”

Do I understand all of that? Not really, but after weeks of constantly nitpicking every decision, it was nice to hear the other robots show some respect for the app. (Though, of course, these LLMs are wired to be sycophants, showering praise on their users.)

There was something empowering about using these tools to create bespoke software. I joked in previous posts in this series that I know nothing about coding, but the process actually teaches you quite a lot about design and many technical details, even while you learn almost nothing about writing in the programming language itself (TypeScript in my case).

This experience led me to a sweeping generalization: 2026 will be the beginning of a golden age of AI tool use. The number of AI tools that bring technological superpowers to amateurs will explode. We are entering the sweet spot where the tools are highly capable, fully under our control, and can make our jobs easier, more interesting, and more productive rather than replacing them. That’s a safe short-term bet. The more difficult question is whether this fun interlude is just a transition period on the way to the more doomsday and sci-fi scenarios of an employment apocalypse or AI misalignment that threatens civilization.

So how’d it do?

I released TelosTax as a free open-source app, so anyone could look at the code and suggest ways to improve it—or determine that it’s beyond repair. Experts can inspect how the TelosTax tax engines work, where the numbers come from, and whether the app accurately implements IRS statutes and regulations. My own testing was relatively limited compared to what a consumer-ready product would require, and I was fully prepared for the possibility that Claude, in its eagerness to please, built me a Potemkin app.

I told Claude to design TelosTax with strict privacy as the core architecture. It has two modes: free and AI-assisted. The free mode is as strict about privacy and data retention as you could possibly get. The entire app runs in your browser. There are no accounts and no cloud services to connect to. After you load the app, you don’t even need an internet connection to use it. No data leaves your device. The app forces you to save and encrypt your tax return, and if you lose your password, there’s no way to recover it.

But I also wanted to have AI tools as an option. If you turn them on, you can dictate or type in plain language any tax information you have, and the AI will enter it for you. You can right-click any element on any page in the app to ask the AI about it. You can do the same with every IRS tax form. The AI will keep track of your filing progress and nudge you when it sees a deduction or credit you might want to take.

Using AI comes at the cost of privacy. What you type or speak into a chatbot is sent to the AI provider’s servers for processing. To partially mitigate this, I built a PII stripper into the app. If you enter addresses, dates of birth, Social Security, credit card, bank account, or other similar personally identifiable information into the AI chat, a warning appears explaining that the information will be redacted before it’s sent. The AI settings include an audit page that logs every AI message and shows exactly what was sent from your computer after you hit send, including any contextual information that is normally invisible. As far as I know, no AI product offers this transparency, even though it was trivial to add.

To use the AI functions, you need a paid Anthropic account and an API key. I chose Anthropic because the company has clearer privacy and data retention policies than OpenAI and Google. (Anthropic says it doesn’t use data sent via API to train its AI models, and it deletes your data after 30 days.) This is probably all a little over-engineered and over-complicated for a demonstration project, but I wanted to really test the limits of whether it’s possible to fully replace a complicated piece of software.

So how did it hold up during the 2026 tax season? For roughly nine out of ten tax filers, the app worked as advertised by Claude. I created several moderately complex federal returns in both TurboTax and TelosTax and got identical results. And several users who were generous enough to do testing for me had similar positive experiences.

But it struggled with highly complicated returns that require power-user functions such as robust document import. A Telos reader who happens to be a CPA found the app choking on his multiple K-1 and 1099 PDFs and, even worse, making errors in self-employment tax calculations.

Software really is dead

But I am convinced that with enough time, any of these bugs could be fixed by Claude or similar frontier models. In playing around with Claude Opus 4.7, released on Thursday, I can already tell it’s significantly more sophisticated and would have caught many of the coding errors that I and other users found in the first versions of the TelosTax app. The key here is the pace of progress. A year ago, you could barely use AI to write complex code. A year later, AI can create highly sophisticated, though still buggy, software that requires significant human testing to perfect. A year from now—and perhaps sooner, given the early reports of Claude Mythos’ capabilities—it will be trivial to create something like TurboTax on your own.

But a year from now, creating an app similar to TurboTax to do your taxes will seem anachronistic. Just over the course of this project, the available AI tools have changed so dramatically that if I were starting over today, it wouldn’t even make sense to build a full-featured tax app that tries to address every tax filer’s unique situation.

We have rapidly moved into the agentic era, where a user simply asks Claude to accomplish a task, and Claude decides which existing tools it will use to complete the job and which tools it might need to build itself.

The AI agent is becoming the starting point for all digital work. Spending any mental energy deciding which app to open to complete a task will become increasingly less common. Most power users have already moved to a model where you grant Claude or a similar agent, such as OpenClaw, wide access to a computer that is always on and then just tell the AI, via your mobile device if you’re out and about, what you want accomplished. This is not exactly a new idea. It’s essentially Apple’s Siri on steroids.

I’ve fully embraced this workflow in my own life. I love nothing more than procrastinating by fiddling with the latest productivity apps. But I’ve ditched almost all of them for Claude. I now start my day by telling Claude what I want to accomplish. The AI asks me a few questions and maps out a plan. It monitors all the apps I used to check obsessively, and pings me when something truly requires my attention. The biggest downside to this new agentic era is that agents handle so much digital scutwork so well that I no longer have any excuse to divert my attention from writing and other high-priority human work.

I find all of this both exciting and terrifying. In the days and weeks ahead, I’m going to return to covering hardcore politics here at Telos, but I also plan to devote more attention to the issues we explored in this series. Drop me a line and tell me what you think.

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You can read Part 1 here and Part 2 here.

Learning to Code, Part 3

Don’t Call It Vibe Coding

AI researcher Andrej Karpathy is a big deal in the tech world. He was a member of the original team at OpenAI, the former head of AI at Tesla, and the founder of Eureka Labs, an AI education startup. A year ago, he coined a term that helped launch an amateur coding…

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Learning to Code, Part 2

Why Everyone Hates AI

My decision to create an alternative to TurboTax came at a good time. Fortunately, you don’t need to know how to code anymore to create software. Unfortunately, you have to use AI if you want to build anything decent, and I shared the same view as so many others: it suc…

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TelosTax

It’s tax filing season, and as I was making my way through TurboTax’s clunky, overpriced app, I started to get frustrated. I’d spent almost $200 on the software, and it kept interrupting my data entry with scammy upsell offers.

Then I hit a screen that blocked me from continuing until I decided whether to agree to a new set of terms. My experience using the app would be much better if I said yes. I read the tiny fine print.

Intuit, the $125 billion company that makes TurboTax, wanted all of my tax data for five years so it could share and monetize it across all of its software offerings, including Credit Karma, the fastest-growing part of Intuit’s data empire.

“Right now, we can only use your tax info to help you prepare and file your return,” an FAQ cheerily noted, “but with your consent, we can do a lot more.” I would be able to “work smarter,” “file faster,” and receive “an even higher level of service.” Buried in the last lines, I learned that my tax return data could be sent to something called the Intuit Product Development Center.

In India.

Unfortunately, the alternatives to paid tax prep software are limited. The IRS used to offer Direct File, a free online tax filing system that was popular and easy to use. But Intuit mounted a massive lobbying and influence campaign, convincing the Trump administration to kill Direct File, which makes the company’s aggressive attempts to monetize the most sensitive financial data of the 40 million Americans who use TurboTax even worse.

I found all of this extremely annoying. But over the winter, Intuit’s fellow tech industry oligarchs delivered a potential solution: AI-coding tools that enable anyone to create software.

So I decided to build my own TurboTax.

I should point out that I know nothing about coding. The last time I remember coding anything on a computer was in 1983, when my fourth-grade teacher, Mr. Bilitsky, taught our class how to use BASIC on a Commodore PET.

I have no specialized knowledge of U.S. tax law.

And yet, in just a few weeks, I created what appears to be a full-featured financial app that prepares complicated federal and state tax returns for free.

It’s TurboTax on steroids.

Naturally, I decided to call it TelosTax. The app guides you through your taxes step by step in an interview mode. If you’re a tax pro, you can enter your info directly on any of dozens of IRS tax forms. It can import your tax documents. It can organize your spending transactions by tax category. It has a dashboard where you can adjust sliders for over 20 different tax variables. It gives you a FICO-like score to assess your likelihood of being audited. The app produces pretty donut and bar charts summarizing your finances and flow visualizations that trace the trajectory of every dollar of your income, deductions, credits, and the taxes you pay.

Without any special skills, I was able to prompt coding tools to translate thousands of pages of U.S. tax law and regulations into an app that can produce a federal tax return for any American—from the simplest W-2 employee taking the standard deduction to a complex filer with, say, farm income, rental properties, asset depreciation schedules, AMT adjustments, crypto sales, a Roth conversion, net operating loss carryforward, and every imaginable combination of deductions and credits.

On the public repository where TelosTax now lives, I’m listed as the “author” of the app’s 234,000 lines of code, despite the fact that I did not write even one of those lines. I asked my new robot friend, Claude Code, the AI that wrote the whole thing, how long it would have taken a human to do the job.

“Without AI assistance,” Claude said, “I’d estimate 2-3 years for one person with the right skills.”

At first, that flattering response made me marvel that I had built something this complicated in just a few weeks.

But then it filled me with dread, because it hinted at the obvious limitations of using these tools without the proper training in coding or tax law. Two-hundred-thirty-four-thousand lines is a lot of code. Like good writing, good code is concise. The frontier AI models—Claude, GPT, Gemini—are trained to be useful and compliant, which makes them sycophantic. Did Claude actually build me a bloated, unmaintainable pastiche of features that proves the opposite of what I intended—that the big software companies have nothing to fear from vibe coding amateurs?

If the app holds up and works as advertised by Claude, I’ll never need to use TurboTax again. But the reverse could be true: maybe Claude, in its effort to please, created a Potemkin app that simply fooled me into thinking it was in the same league as a product designed by hundreds of engineers at a Fortune 500 company.

To help answer that question, I’m making the app public as a free open-source project so tax professionals and actual human coders can vet it. The idea behind this series is to explore two related issues:

• Whether new AI-coding tools are really up to the task of replacing premium software

• How journalists can use AI, which everyone seems to hate, for a positive public-interest goal

So consider TelosTax an experimental prototype and don’t use it to prepare your taxes unless your return is carefully reviewed by a professional. It’s possible Claude got everything wrong. If you’re a tax professional or programmer who would like to help stress-test the app, please email me at ryan@telos.news. But anyone can play around with it, dig into the code, and contribute to the project. You can check out the code and documentation on GitHub, and the app is now live at its new home: https://telostax.app. I’ll report back on how it holds up, and whether Intuit has anything to worry about.

The rest of this series is divided into four parts that track my own circuitous journey exploring these issues over the last month:

• Part 1 (Today): How Intuit Killed Direct File — The story of Intuit’s attack on a popular program—and how the Trump administration gave the company everything it wanted

• Part 2 (Wed): Why Everyone Hates AI — To build my own bespoke software, I had to confront my knee-jerk hostility to AI, which I had come to associate purely with slop and an impending jobs apocalypse—starting with journalism. I was wrong (mostly).

• Part 3 (Thu): AI Comes for the Coders — A look at how coders have navigated the end of coding and the lessons that journalists—and every other white-collar profession—can learn from them

• Part 4 (Fri): The AI Rabbit Hole — My own weird experience falling down the rabbit hole of AI-coding to build a tax app

It’s been a fun ride, and I’m glad to finally get to share all of the details with you.

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Part 1: How Intuit Killed Direct File

Why we can’t have nice things (tax-filing edition)

Intuit’s invasive privacy policies sent me on an odyssey to understand how the hell they get away with this. The simple answers are: money and Trump.

Since 2015, Intuit has spent $33 million on an influence campaign in Washington, D.C., to make it more expensive for Americans to file their taxes. The company’s number one goal, as laid out in lobbying disclosures and SEC filings, was to stop the federal government from providing a free, simple tax-filing system.

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I threw a lot at it. At a certain point, it started cutting corners. The more I asked it to d…

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—Ryan

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☀️ Afternoon Briefing — Wednesday, February 11, 2026

A 5-minute read on a day …

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Yesterday’s experimental AI-assisted newsletter drew mostly negative reactions in the comments. Some of that is fair—it was way too long. But there’s a deeper issue: once something is labeled AI, it immediately changes how people experience it.

I’m not immune to that reaction. If I loved a new song and then learned it had been created with AI, I’d stop l…

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Last week Anthropic, which makes the Claude chatbot, quietly released some plugins for Claude, including one that performs legal services. Wall Street freaked out.

Investors didn’t just punish companies tied directly to the legal profession. They dumped a much broader swath of stocks across software, financial data, and real estate. For two days, markets…

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Alex Jeffrey Pretti was an unarmed protester who was shot in the back and murdered by federal agents, who continued to fire at him even after he was lying on the ground, lifeless.

One of the agents who surrounded Pretti literally applauded as his colleague murdered Pretti.

The videos are not ambiguous. They clearly show an agent …

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Chairman Trump

Over the last few days, with all the attention on Donald Trump trying to take over Greenland, his plan to create and lead an institution he said “might” replace the United Nations has escaped scru…

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Combat Journalism

Given all the twists and turns of this long, multi-part story and the often bizarre and sensationalistic details, I realize that some readers may have lost sight of something: the biggest and most newsworthy revelation of this series is that Robert F. Kennedy Jr. conspired with a reporter to abuse a D.C. court so he could save his relationship with Trump and become the next Secretary of Health and Human Services.

We are living in a new era of combat journalism in which any high-profile political reporter will encounter ferocious bad-faith attacks from those in power. And during the Trump era, the attacks have intensified from harsh language—“enemy of the people”—to using the machinery of government to target reporters.

It started with civil lawsuits, usually defamation, to harass reporters with time-consuming litigation, intrusive discovery requests, and the depletion of bank accounts. Last year, it grew to encompass the unprecedented use of state power to shape the editorial policies of newsrooms within large companies subject to government regulation.

This week, the legal harassment escalated to the next step: the use of the criminal justice system to seize a Washington Post reporter’s laptops and phone, potentially giving the Trump administration access to all her confidential sources and other highly sensitive information.

Like most political journalists, I have witnessed plenty of hostile rhetoric, both from activists on the margins of politics and from high-level government officials. I’ve also been the target of a frivolous defamation lawsuit from one of the most powerful officeholders in Washington. And unfortunately, I have also seen up close how political actors can weaponize criminal charges against a reporter to prevent him from reporting unwelcome information.

In my case, a future cabinet secretary and one of Trump’s most important campaign allies persuaded his paramour, my ex-fiancée Olivia Nuzzi, to file a false complaint against me to stop me from writing about him in the weeks before the 2024 election.

The longtime legal and political writer Scott Lemieux, who correctly noted that the “heart” of this story is “that Nuzzi’s goal was to suppress damaging information about RFK Jr. both to help Trump and to protect RFK Jr.’s chances of becoming” HHS Secretary, has described these revelations as “almost certainly the biggest scandal in the modern history of American journalism.”

Bigger, he argues, than Judith Miller, whose pre-Iraq war reporting for the New York Times was part of “one of the worst systemic failures in the history of American journalism,” according to New York magazine.

Bigger than Stephen Glass, who committed “the most sustained fraud in modern journalism,” according to Vanity Fair.

Bigger than Jayson Blair, whose fabrications and plagiarism at the Times were “a low point in the 152-year history of the newspaper,” according to the Times itself.

“Why didn’t you tell anyone?”

Given the scale of the Kennedy-Nuzzi scandal, the question I’ve been asked most frequently is, “Why didn’t you tell anyone about all of this when it could have mattered?”

Maybe it could have changed the election.

Maybe it could have affected Kennedy’s confirmation.

Maybe it could have prevented several major media companies from hiring, publishing, and promoting the work of a journalist who crossed such serious ethical lines.

I’ve already explained, in excruciating detail, what happened to prevent the story from being told before the 2024 election.

But what about after that? Many of you have asked me what happened after Nuzzi was forced to withdraw her false claims in D.C. Superior Court on November 8, and I returned to Politico as its Chief Washington Correspondent.

Politico never ran an article about any of this. Why didn’t I tell Politico’s editors about what I knew, which would have been a sensational story for Politico to investigate and publish?

The answer is that I told Politico’s top editor everything.

After its investigation of Nuzzi, New York magazine issued a statement absolving her of wrongdoing. Why, given what I knew, didn’t I tell New York about Nuzzi’s journalistic fraud?

The answer is that I told a senior editorial staffer at New York everything.

Simon & Schuster allowed American Canto out into the world without basic vetting. I had a working relationship with the editor and publisher of Avid Reader, the imprint that published the book. Why didn’t I tell one of them what I knew?

The answer is that I told the publisher everything.

To help promote her book and her return to journalism, The New York Times published a puff piece on Nuzzi, accompanied by a glamorous video and photo essay. Political reporters at the Times, several of whom knew the real story, told me they were appalled by the article, which was eviscerated by Times readers as “hagiography,” “a toothless examination,” and “a fashion shoot” serving as “clickbait.” But I was quoted in the article, so why didn’t I tell the reporter what I knew, which could have saved him and the newspaper from embarrassment?

The answer is that I told the Times reporter who wrote the article everything.

Mark Guiducci, the editor-in-chief of Vanity Fair, and his superiors at Condé Nast, hired Nuzzi as an editor and published a widely panned excerpt from her book without conducting basic due diligence about this scandal. The magazine claimed it was “taken by surprise” by the revelations of Nuzzi’s journalistic malfeasance. Shouldn’t they have known better?

The answer is, yes, they should have.

“Why didn’t they care?”

These media companies either knew about, or, in the case of Vanity Fair, should have known most of what I reported in this series, including:

• Kennedy’s role in weaponizing a domestic violence court against a journalist to prevent the publication of damaging reporting about him

• Kennedy’s alleged use of psychedelics and ketamine

• Kennedy’s toxic manipulation of a female reporter 39 years younger than him (I recommend this TNR piece by Nina Burleigh if you think this doesn’t matter.)

• Kennedy’s knowledge of the illegal recording of Donald Trump at Mar-a-Lago, from which he may have gained valuable information to aid him in his endorsement negotiations with Trump

• Kennedy’s extreme recklessness and poor judgment in regularly masturbating on camera for a reporter and soliciting and sending the reporter explicit pictures and graphic poetry both before and after his security adviser told him that his phone had been hacked (again, read the Burleigh piece if you recoil at the thought of this being part of the public discourse)

• Nuzzi’s year-long effort working as a political operative for Kennedy while covering the presidential campaign, including catching and killing negative stories and betraying confidential sources to Kennedy

The real question isn’t, “Why didn’t I tell anyone?” The real question is, “When I did, why did no one seem to care?”

I think I know the answer.

So I’m going to take you behind the scenes at each of these five institutions—Politico, New York magazine, Simon & Schuster, The New York Times, and Vanity Fair/Condé Nast—to explain how these pillars of the American media not only ignored this story, but tried to bury it, favoring instead the fictitious counternarrative spun up by Nuzzi and Kennedy to evade accountability.

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In this email are the two concluding sections of the series. The final installment of the Bamboo Series will land later this week. And I’ll also have something fun for you tomorrow. As always, thanks for reading!

—Ryan

VIII. Chain of Custody

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The subject line got right to the point: “MURDER COVER UP.”

On December 7, Cornwell sent an email to Volzer, the conservator; Elliott P. Park, Biss’s receiver; and Tenley Carroll Seli, the official handling Biss’s case at the Virginia State Bar.

“So anybody want to explain where Steve got 3 million dollars after Jim Dimartino’s death when he was suspended the entire prior year?” she wrote. “OH YEAH that would the 506 exception that they used to divvy up companies they stole using the SEC. So iam going to get steve’s tax returns today from where I store my stuff to demonstrate that at no time did steve ever make this kind of money. So enjoy the notoriety. You are covering up murder, there is an innocent man in jail.”

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In this email is Part VII—where the plot takes a turn from weird to insane. I’ll send the ending to this piece tonight, and I’ll also post a podcast version in case you want to listen to the entire article.

The final installment of the Bamboo Series will land later this week. Thanks for reading!

— Ryan

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VII. The Conservator

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On August 30, two weeks after Biss’s stroke, Harvey J. Volzer, a Virginia lawyer, sent an email to Biss’s estranged wife, Tanya Cornwell.

“If you bring Steve’s lap top next Tuesday, I will get it to Kevin Hooks,” he said. “We also can discuss any additional documents/pleadings regarding Steve.”

Hooks is a prominent private investigator in Virginia whose firm, Interprobe, offers, among other services, “device data extraction.”

Cornwell responded early in the morning on September 5: “I took care if [sic] the computer last week.”

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VI. Dodecahedron

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On the morning of August 16, 2023, Biss started his day the way he usually did, scanning right-wing news sites and posting on Truth Social. He had a signature formula in which he would write a pithy all-caps headline above a short summary of the article.

He started at 6:25 AM with “YOU’RE NEXT” about a Daily Caller article summarizing a Josh Hawley appearance on Fox News.

He posted a few items about Trump’s legal cases. “These are deeply corrupt Democrats acting in concert to harm one man,” he noted about the Georgia indictment. “Truth by any means is the only path to victory.”

He finished up at 7:48 AM with the last of several posts about trans issues. “Muslim transgender wants balls back,” he wrote.

It was the last thing Biss ever wrote on Truth Social.

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V. Substantially, Objectively True

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What Colloton didn’t know, if indeed he had his eye on killing Sullivan, was just how bad our case would be for that cause. Back in Iowa, we got just about everything we wanted out of discovery: the results of an I-9 audit that NuStar had conducted after my article appeared, an order directing the Social Security Administration to provide us with information about every NuStar employee since 2006, and even some limited information about who might be funding the case.

We had an ex-ICE special agent, Claude Arnold, who was formerly the chief of ICE’s Transnational Gang unit at ICE Headquarters in Washington, DC, review the massive record we had assembled. He produced a devastating expert report that was not made public but has subsequently been unsealed.

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IV. Never Tweet

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A rational person might have withdrawn the lawsuit at that point. This was clearly going to end in embarrassment for the dairy. But the case suddenly got new life.

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III. Taking the Fifth

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Steven Scott Biss was one of the strangest and most unpleasant people I have ever encountered. He’s from Canada but became a hardcore America Firster and Trump devotee. He seemed to spend most mornings posting links to Breitbart and The Federalist on Truth Social. There were rumors that his lawsuits were funded by mysterious right-wing benefactors. But he seemed to have little assistance with his filings, appeared to be constantly overwhelmed by the number of cases he had, and often overlooked or abandoned potentially promising avenues of strategy in his big cases.

Biss also had a checkered past.

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I. The Laptop

In late summer 2023, someone broke into the law firm of well-known Charlottesville, Virginia, attorney Steven Biss. His office was allegedly “ransacked,” folders with Biss’s documents went missing, and his laptop, which contained “all” of his “client files,” was gone, “taken by an unknown person.”

Considering Biss’s client list, this was no small matter.

Biss not only represented Donald Trump’s media company, Trump Media and Technology Group (TMTG), which runs Truth Social, but also a network of MAGA luminaries who now populate the upper ranks of the Trump administration, including Kash Patel, the director of the FBI; Dan Bongino, the FBI’s deputy director1; and Devin Nunes, who was the top Republican on the House Intelligence Committee and is now the CEO of TMTG and the chair of the President’s Intelligence Advisory Board.

Biss’s “client files” included a lot more than just the sensitive personal information of top Trump intelligence and law enforcement officials. In Biss’s possession were also sensitive secrets from some of the world's biggest media companies.

Biss is best known for suing reporters and news organizations for defamation. Several of his high-profile cases reached the discovery phase, when thousands of pages of internal documents were produced by both his MAGA plaintiffs and the media defendants they sued, including CNN, The Washington Post, NBCUniversal, and Esquire, where I previously served as Chief Political Correspondent.

Many of the documents produced during discovery in these cases were shielded from public disclosure—and even to the opposing client—by “counsels-eyes-only” protective orders. When sensitive documents were included as exhibits or in motions, they were often redacted or filed under seal. For instance, in a lawsuit filed by the family of Michael Flynn against CNN, “highly confidential” documents were sealed at the request of Biss, and “confidential exhibits” were filed by CNN. In a Nunes case against NBC, a broad protective order covers “confidential, proprietary, or private information” exchanged in discovery, including “newsgathering information,” “competitively sensitive information,” and any personal information that, if disclosed, “would cause injury.” In a Nunes case against The Washington Post that touches on classified intelligence matters, the docket includes numerous sealed filings and references to “highly Confidential Material.”

These public dockets only hint at what was in Biss’s stolen computer if it included “all client files,” because the universe of confidential material produced in discovery is much larger than what’s formally used in a case.

I know firsthand the kinds of sensitive information that parties exchange during discovery in a complicated defamation case. Nunes, Biss’s most prolific plaintiff, and Nunes’s family, filed a pair of lawsuits against Esquire and me in 2019 and 2020 over an article I wrote about the use of undocumented labor at the dairy owned by Nunes’s parents. Backed by a brilliant and dogged team of lawyers at Hearst, which owns Esquire, I spent the last six years fighting Nunes and Biss in court.

Biss’s case files in my lawsuit would include the names and personal information of undocumented workers hired by the Nunes family dairy in Sibley, Iowa, Devin Nunes’s tax returns and phone records, information we subpoenaed from Trump’s media company, files related to a political group founded by J.D. Vance, and sensitive reporting files that I turned over under the strict terms of a protective order.

Being targeted with frivolous litigation by one of the most powerful officials in America wasn’t fun. The case—and the cartoonish demand for over $100 million in damages—hung over me for years. It made it more difficult to report on Trump and his allies. It forced me to spend untold hours responding to burdensome discovery requests and preparing for two day-long depositions as well as a potential trial.

But it also gave me a much deeper understanding of the defining feature of President Trump’s first year in office: the weaponization of the government on behalf of Trump and the MAGA movement against their critics.

I learned a lot tangling with Nunes and Biss, and much more when I started down the rabbit hole of what happened to Biss—and his computer—after Biss suddenly disappeared from our case in 2023. I learned what it’s like to be targeted by powerful government officials who don’t approve of what you say about them, something many ordinary Americans and institutions have now experienced in 2025. I learned what it’s like inside the right-wing effort to turn back the clock on press freedoms. And I learned that the lawyer at the heart of it all, the one who lost that laptop with all of those MAGA and media secrets on it, had some secrets of his own.

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II. Devin’s Journey

When I first met Rep. Devin Gerald Nunes a decade ago, he was not who he is today.

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