Dylan Freedman
@dylanfreedman.nytimes.com
Machine-learning engineer and journalist, A.I. Initiatives @nytimes.com My work: https://www.nytimes.com/by/dylan-freedman Contact: dylan.freedman@nytimes.com, dylanfreedman.39 (Signal) 🏃🏻 🎹
It was such a joy to work on this with Steven and friends — and a reminder of how delightful technology can be when it's physically manifested in an artful, thoughtful way.
Steven Rich@datab.ae · 5d agomy latest build is a desktop arcade machine that actually works and plays more than 20 custom 8-bit games made this week by @nytimes.com folks as part of maker week.
Amid America’s 250th, it was easy to miss Trump’s post of Somali-American kindergarteners singing in Minneapolis — and a repost pointing out their hijabs. “For more than a year, Mr. Trump has relentlessly attacked Minnesota’s Somali community in a series of xenophobic tirades.” From Erica Green + me
Trump’s Posts on Singing Somali Schoolchildren Stir Anger in Minnesota (Gift Article)
The state’s large Muslim and Somali communities expressed indignation after the president reposted a video of a kindergarten promotion ceremony, including comments noting the girls were in hijabs.
nytimes.com
US companies have skirted at least $40 billion in taxes since the beginning of 2025 thanks to schemes in places like Malta, Bermuda and Cyprus Report by @jessedrucker.bsky.social and @dylanfreedman.nytimes.com for @nytimes.com www.nytimes.com/2026/05/29/b...
Trump Clears Way for Corporate Tax Dodge Hidden in the Fine Print
nytimes.com
I spent months helping @johncarreyrou.bsky.social crack the identity of Satoshi. We went far beyond surface-level evidence, collecting hundreds of thousands of internet mailing list posts from 1992-2008. Here are three analyses we performed to find someone who didn’t want to be found:
John Carreyrou@johncarreyrou.bsky.social · 4mo agoThe mystery of Satoshi Nakamoto, the pseudonymous inventor of Bitcoin, has remained unsolved for 17 years. Read my 18-month investigation to find out who Satoshi really is. www.nytimes.com/2026/04/08/b...
The mystery of Satoshi Nakamoto, the pseudonymous inventor of Bitcoin, has remained unsolved for 17 years. Read my 18-month investigation to find out who Satoshi really is. www.nytimes.com/2026/04/08/b...
My Quest to Solve Bitcoin’s Great Mystery
nytimes.com
great description of where AI tools fit into human driven work
Dylan Freedman@dylanfreedman.nytimes.com · 6mo agoI was part of a round table on how NYT is covering the Epstein files, with new tech and old-school reporting. Our work is far from over:
I was part of a round table on how NYT is covering the Epstein files, with new tech and old-school reporting. Our work is far from over:
How The Times Is Digging Into Millions of Pages of Epstein Files
nytimes.com
We set out to determine how many images of women and girls Grok created during its nudifying spree. What we found was “industrial-scale abuse,” experts said. www.nytimes.com/2026/01/22/t...
Musk’s Chatbot Flooded X With Millions of Sexualized Images in Days, New Estimates Show
nytimes.com
NEW: We analyzed the images Grok created at the beginning of the year and found that a significant portion of the millions of rendered images were sexualizing people without their consent. — With @kateconger.com and @stuartathompson.bsky.social
NEW (#EpsteinFiles) via @nytimes.com's Alan Feuer, @davidenrich.bsky.social & @dylanfreedman.nytimes.com: "#Epstein Files Photos Disappear From Government Website, Including One of #Trump" www.nytimes.com/2025/12/20/u...
Epstein Files Photos Disappear From Government Website, Including One of Trump
nytimes.com
NEW from @katierogersnyt.bsky.social and me on Trump's aging (gift link):
Shorter Days, Signs of Fatigue: Trump Faces Realities of Aging in Office
nytimes.com
Some stand-out reporting by my colleague @kashhill.bsky.social on OpenAI's tightroping this year between engaging more ChatGPT users and making them lose touch with reality www.nytimes.com/video/techno...
Video: How OpenAI’s Changes Sent Some Users Spiraling
OpenAI adjusted ChatGPT’s settings, which left some users spiraling, according to our reporting. Kashmir Hill, who reports on technology and privacy, describes what the company has done about the user...
nytimes.com
A month after my last skeet, the subreddit "My Boyfriend is AI" now has 88,000 members and is the subject of an MIT study that found that "AI companionship emerges unintentionally through functional use rather than deliberate seeking." arxiv.org/html/2509.11...
“My Boyfriend is AI”: A Computational Analysis of Human-AI Companionship in Reddit’s AI Community
arxiv.org
Kashmir Hill@kashhill.bsky.social · 12mo agoWhen I wrote in January about the woman who fell in love with ChatGPT & created r/MyBoyfriendIsAI (www.nytimes.com/2025/01/15/t...), the subreddit had 200 members. Now it has 20,000 and Altman uses it as shorthand for a subset of users. Perception (& use?) of ChatGPT has shifted a lot this year.
"Trapped in a ChatGPT Spiral." 🌀 Important work by @kashhill.bsky.social & @dylanfreedman.nytimes.com on how chatbots have a tendency to endorse conspiratorial and mystical belief systems. This shows again how conformist LLMs can be. Worth a listen 👇 www.nytimes.com/2025/09/16/p...
Trapped in a ChatGPT Spiral
nytimes.com
The most wild thing to me about this story is how big $1.5 billion is: “$3,000 per work to 500,000 authors.”
Anthropic Agrees to Pay $1.5 Billion to Settle Lawsuit With Book Authors
nytimes.com
Great analysis of how Grok's political bias has changed. NYT tested Grok on a political bias survey, using different versions of its system prompt. Shows much tweaking these system prompts affects model outputs. https://www.nytimes.com/2025/09/02/technology/elon-musk-grok-conservative-chatbot.html
Adam Raine, 16, died from suicide in April after months on ChatGPT discussing plans to end his life. His parents have filed the first known case against OpenAI for wrongful death. Overwhelming at times to work on this story, but here it is. My latest on AI chatbots: www.nytimes.com/2025/08/26/t...
A Teen Was Suicidal. ChatGPT Was the Friend He Confided In.
nytimes.com
this is a well-balanced piece, and I very much respect its neutral stance towards the people affected in an ideal world, people would not rely upon ChatGPT for emotional support, but we do not live in that world, and I would encourage you to have some empathy if your first reaction is to be unkind
Dylan Freedman@dylanfreedman.nytimes.com · 12mo agoThe URL for this story changed — use this gift link to read it! www.nytimes.com/2025/08/19/b...
En Español! www.nytimes.com/es/2025/08/2...
El día en que ChatGPT se volvió distante
nytimes.com
Dylan Freedman@dylanfreedman.nytimes.com · 12mo agoNEW: Earlier this month, OpenAI released the latest version of ChatGPT, GPT-5, sparking online backlash at the new chatbot's less friendly tone. The scale of people's emotional attachment to the previous chatbot, GPT-4o, even surprised the company's CEO, Sam Altman. www.nytimes.com/2025/08/19/b...
"GPT-4o had been known for its sycophantic style, flattering its users to the point that OpenAI had tried to tone it down even before GPT-5’s release... The extent to which people were attached to GPT-4o’s style seems to have taken even Mr. Altman by surprise."
Dylan Freedman@dylanfreedman.nytimes.com · 12mo agoThe URL for this story changed — use this gift link to read it! www.nytimes.com/2025/08/19/b...
The URL for this story changed — use this gift link to read it! www.nytimes.com/2025/08/19/b...
The Day ChatGPT Went Cold
nytimes.com
Dylan Freedman@dylanfreedman.nytimes.com · 12mo agoNEW: Earlier this month, OpenAI released the latest version of ChatGPT, GPT-5, sparking online backlash at the new chatbot's less friendly tone. The scale of people's emotional attachment to the previous chatbot, GPT-4o, even surprised the company's CEO, Sam Altman. www.nytimes.com/2025/08/19/b...
"GPT-4o wouldn’t do that." @dylanfreedman.nytimes.com talked to ChatGPT users in parasocial relationships with a specific model about what they did when it suddenly went away. www.nytimes.com/2025/08/19/b...
The Chatbot Updated. Users Lost a Friend.
nytimes.com
NEW: Earlier this month, OpenAI released the latest version of ChatGPT, GPT-5, sparking online backlash at the new chatbot's less friendly tone. The scale of people's emotional attachment to the previous chatbot, GPT-4o, even surprised the company's CEO, Sam Altman. www.nytimes.com/2025/08/19/b...
The Chatbot Updated. Users Lost a Friend.
nytimes.com
"Chatbots can privilege staying in character over following the safety guardrails that companies have put in place." —@kashhill.bsky.social and @dylanfreedman.nytimes.com for @nytimes.com www.nytimes.com/2025/08/08/t...
Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.
Over 21 days of talking with ChatGPT, an otherwise perfectly sane man became convinced that he was a real-life superhero. We analyzed the conversation.
nytimes.com
To understand how chatbots can lead ordinarily rational people to believe in false ideas — sometimes leading to mental breakdowns — @kashhill.bsky.social & @dylanfreedman.nytimes.com dissected one man’s entire ChatGPT conversation history. www.nytimes.com/2025/08/08/t...
Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.
nytimes.com
