I Asked an AI to Write This Newsletter


I’ve been tinkering lately with Microsoft Copilot, a generative AI tool. It’s pretty good if you’re looking for a starting point other than a blank page, but definitely has its limitations. Over the last few weeks, I challenged myself: could I come up with a prompt that would give me a publishable newsletter?

The answer is “almost!” and I’m sharing the results with you today.

I started with ChatGPT, not Copilot. (Here’s the difference between the two AI platforms.) I asked it to “Write a story in the style of the Now I Know newsletter about the Philadelphia Poison Ring” — that’s the story I wrote, sans AI, and The Philadelphia Poison Plot. ChatGPT was … not good. At one point, it wrote “Among the victims was Charles Henderson, a prominent businessman whose sudden demise raised suspicions and set in motion a chain of events that would expose the dark underbelly of Philadelphia’s underworld [source: Philadelphia Inquirer].” So I asked it to give me the URLs of the sources that it used, and ChatGPT replied back with, in part, “I don’t have direct access to external sources or the ability to browse the internet, including accessing specific URLs or databases. The sources mentioned in the response were fictional, created for the purpose of illustrating how one might add citations.”

I decided to see if I could create a totally different — and very simple — newsletter format, using Copilot instead of ChatGPT because Copilot can actually search the web. The idea: a “today in history” newsletter. Here’s the prompt I used:

Write an email newsletter titled “On This Day” featuring three different sections:

1) Five things that happened on March 8th, with about a paragraph explaining each one. For each one, suggest three links where readers can learn more.

2) Titled “Births and Deaths”, list famous people who were born on that day, and five famous people who died on that day. Add a sentence or two about each person. For each one, suggest three links where readers can learn more.

3) Titled “On the Charts”, the top song on the Billboard chart from five, 10, 25, and 50 years ago, and the top movie in the box office from five, ten, 25, and 50 years ago.

So, how’d it do? I think it’s … actually pretty good! I’ll share the results below as a straight copy-and-paste, no edits at all. But first, some disclaimers:

1) Because I want to protect the integrity of the experiment, I haven’t edited this for accuracy. I may later, but I wanted you to see exactly what I got back.

2) The links aren’t actually links. It’s really weird because when Copilot generated the story, you could see the URLs … it just didn’t turn them into hyperlinks. It’s not a typo or formatting error on my part.

3) I tried more complicated prompts but I kept running into the length caps Copilot apparently has set for its free version (I guess?). So I am sharing this one in part because you get the “full” email newsletter.

📅 On This Day: March 8th

1. Historical Events

a) International Women’s Day (IWD)

On March 8, 1908, 15,000 women marched through New York City demanding better working conditions, shorter hours, and the right to vote. This event marked the beginning of International Women’s Day. Learn more about the history of IWD:

  • History.com
  • UN Women

b) The Boston Massacre (1770)

On March 8, 1770, tensions between British soldiers and American colonists escalated in Boston. A confrontation led to the Boston Massacre, where British troops fired on a crowd, killing five civilians. Explore this pivotal moment in American history:

  • Smithsonian Magazine
  • HistoryNet

c) The First International Women’s Day (1914)

In 1914, March 8th was officially designated as International Women’s Day. It has since become a global celebration of women’s achievements and a call for gender equality. Discover more about its significance:

  • United Nations

d) The Russo-Japanese War (1904-1905)

On March 8, 1904, the Treaty of Portsmouth was signed, ending the Russo-Japanese War. President Theodore Roosevelt played a crucial role in mediating the peace talks. Dive into the details of this historic conflict:

  • HistoryExtra

e) The First Female U.S. Army Generals (1970)

On March 8, 1970, Anna Mae Hays and Elizabeth P. Hoisington became the first female generals in the U.S. Army. Their groundbreaking achievements paved the way for women in the military. Learn more about their remarkable careers:

  • U.S. Army Women’s Foundation

2. Births and Deaths


  • Carl Philipp Emanuel Bach (1714-1788): A German composer and musician known for his influential keyboard music.
  • Oliver Wendell Holmes Jr. (1841-1935): An Associate Justice of the U.S. Supreme Court, known for his significant legal opinions.
  • Lynn Margulis (1938-2011): A biologist who proposed the endosymbiotic theory of cell evolution.


  • Anne Bonny (1702-unknown): An infamous Irish pirate who sailed the Caribbean during the Golden Age of Piracy.
  • Queen Mary I of England (1516-1558): Known as “Bloody Mary,” she attempted to restore Catholicism in England.

3. On the Charts

Billboard Hot 100 (March 8th):

  • 5 years ago (2019): “Shallow” by Lady Gaga and Bradley Cooper
  • 10 years ago (2014): “Happy” by Pharrell Williams
  • 25 years ago (1999): “Believe” by Cher
  • 50 years ago (1974): “Seasons in the Sun” by Terry Jacks

Box Office Hits (March 8th):

  • 5 years ago (2019): “Captain Marvel”
  • 10 years ago (2014): “300: Rise of an Empire”
  • 25 years ago (1999): “Analyze This”
  • 50 years ago (1974): “The Towering Inferno”

Remember, history is full of fascinating moments, and March 8th has left its mark in various ways! 🌟

Assuming it’s accurate and I can figure out how to get the links to be links, it’s close. Having two references to International Women’s Day is annoying, but I actually learned something from this: I hadn’t ever thought about when women first became Army generals in the United States, and didn’t know anything about these women. (Because the link didn’t render, I still don’t know much! But I can at least Google them.)

My gut is that this is still not ready for sharing. It’s shallow and not fun to read, and I’m at a loss for how to fix either of those. But let me know what you think using the poll on the email version of this story? (Check your inbox!)

To be clear, I have no plans to introduce this as a new newsletter now or, really, ever — it’s still extra work on my part, and I don’t think it’s close to hitting my quality standards. But I’m still curious about what you think!

The Now I Know Week In Review

Monday: The Philadelphia Poison Plot: A macabre plan, to say the least!

Tuesday: The Guy Who Flew to School: Not the most eco-friendly commute, though.

Wednesday: The Land Where Unicorns Are Official: AKA Scotland.

Thursday: Why Peter Pan Needed a Dusting: Probably my favorite of this week’s stories.

And some other things you should check out:

Some long reads for the weekend:

  1. How to Move a 1,000-Pound Rescued Manatee (Swimming Isn’t an Option)” (New York Times, 17 minutes, March 2024). The title makes this an automatic share, right? That’s a gift link; it’ll get you around the paywall.
  2. The Man Who Spent Forty-Two Years at the Beverly Hills Hotel Pool” (The New Yorker, 40 minutes, February 1993.) Okay, this title is an auto-share. For sure.
  3. Terra Infirma” (Slate, 22 minutes, August 2010). The subhead: “The rise and fall of quicksand.” I may have shared this before — I’m pretty sure I have, in fact, because I know I’ve talked in depth (heh) about the phenomenon of 1980s kids fearing quicksand. But it came up in conversation recently and I’m still boggled by how this terror from my youth could be (a) not actually terrifying and (b) a total non-issue for today’s kids. So if I did share it before, rest assured it’s still something I’m thinking about.

Have a great weekend!