Essays
Boston Model room in City Hall. (Photo by Ed Lyons)
About my Essays
I've done all kinds of media (see my media page here) and my podcasts, of course, but writing essays on Medium is something I have really enjoyed. Also, a few of these essays have spurred lots of other media appearances. All of my Medium work is available here, but I below I will highlight the following pieces, and why they mattered:
The Positional Player (2020)
Drinking the Sand (2019)
A Prayer to Athena (2015)
A New American Politics (2016)
Dear Rockport GOP (2015)
A Robot Political Expert Has Just Arrived (Dec 2022)
When OpenAI released ChatGPT, it became an Internet sensation in how incredibly knowledgeable and human-like it was. I decided to write a 2,500-word piece about why it mattered to politics and policy. I saw a lot of human politics in the problems that this version of GPT technology had, and also that we will project our needs on it. This was a Massachusetts-flavored tour of what this technology can do, and my questions revealed both its strengths and weaknesses. They also revealed problems in what humans know.
Very few people read this piece. But the feedback was very positive.
The Positional Player (January 2020)
This piece took me a long time to write. It’s 8,300 words, including the footnotes. I’d wanted for almost a year to use a long chess metaphor to describe how Baker operates in a very different way than previous governors. It’s section four of six in this essay. I was pleased with how this piece came out. The photos from Baker’s flickr feed were very helpful.
Drinking the Sand (2019)
This piece was written right before the MassGOP chose a new party chairman. It was primarily about problems in the party, and how both the establishment and the base activists had different illusions about the state of the party. This piece did well, and I did some media around it. I really liked how the language turned out. Lots of good lines and allusions within. One of my favorite pieces.
The Health Connector Autopsy Report (August 2014)
Nothing I have done has made a bigger difference in my life or in Massachusetts politics as my investigative piece to explain why the Massachusetts Health Exchange failed in October of 2013.
I had a close friend who was one of thousands of MassHealth recipients who suffered when the Health Connector failed in 2013. As a technologist, I decided I could figure out why. I spent months finding out why it happened, and why the media had missed the story. There was a lot of slogging to do, and the whiskey bottle in the above picture near some of the documents above, wasn't a prop. While I was doing all this research, my wife thought this nighttime project was insane, like other crazy projects I'd undertaken. But she was a college journalist as I was, and when I showed her the technical audit reports that nobody noticed, she understood the import immediately.
My 36,000-word report - showing why it happened and how the government knew long in advance it would fail - gained a huge audience. Thousands read it and scores contacted me privately. As it landed in the middle of the gubernatorial race in 2014, it resulted in me meeting Charlie Baker, who cared very much about why the exchange failed, especially as a former health care CEO. The results of my report made it into his campaign and even an answer of his in a televised debate with Martha Coakley.
It also got the attention of the Columbia Journalism Review, which is probably the most important watchdog journalism group in America. Trudy Liberman interviewed me six times to get the entire story, and then wrote this piece, finding that yes, the media had missed the story about why the exchange failed.
Massachusetts journalists were skeptical about my report. But once CJR had blessed it, many contacted me to say congratulations, and we all became friends. Charlie Baker won the election, and appointed me to his policy transition committee to give some advice about how government could handle technology better.
A Prayer to Athena (May 2015)
In January 2015, the public was surprised to learn we were a candidate for the US slot in the competition to host the Olympics. A secretive committee full of Boston business and philanthropic leaders, working with Boston's Mayor Walsh, had submitted a bid to the US Olympic Committee. That Boston group was called Boston 2024. They made a few ads about the "power of sport" - but their real client was the US committee, not the public.
Boston was divided, and divided would mean we'd lose the bid. I was surprised that the elite backers of the Olympic bid were so simplistic and unyielding in their messaging, despite the checked history of hosting the games. Why weren't the elite managing their PR better? Why wasn't there a vision specifically about Boston? I didn't know any of the wealthy and powerful people on Boston 2024. But I despite that, I decided I would write something that would get their attention; that would show them what the vision really was. That became an essay of 10,000 words and many beautiful, on-message pictures of what Boston is, and can be. An opponent of the games saw the link I posted in Twitter, and laughed at me. 10,000 words? No one will read it.
He was wrong.
I watched the Medium site referrer logs pass through all the organizations where the elite worked. For example, I knew exactly when John Fish and his assistant read the piece. Same for the Mayor's office. And the Governor's. Same for Hill Holiday (who even re-tweeted the story). The links from emails were in the hundreds. It was being emailed all over the city.
One of the founders of the bid found me and told me that this was the vision he'd had all along, but couldn't articulate.
The elite said little about the essay publicly (only one CEO had the guts to tweet the link), but the Boston 2024 messaging changed to what I recommended. The next video ad from Boston 2024 came out, and near the end, it panned across a hard-to-find statue, barely visible from the Charles River: the only outdoor statue of Athena. I smiled, and in my mind, took a bow.
A New American Politics (January 2016)
Sizing up the incredible first year of Baker's administration was a huge task. He was so different - and often not even what Republicans expected. But I felt great about this piece, which gained a favorable audience at the highest levels of state government. Here is an excerpt from the introduction:
"This 5,200-word essay is about how Charlie Baker, a Republican in a land of Democrats, embarked on a journey to create a new politics. It should make you proud, regardless of what party you identify with, as it is a great Massachusetts story."
The Party of Charlie Baker (January 2015)
This popular, 9,000-word essay was my first long-form effort at talking about the Massachusetts Republican Party. It was a personal memoir of the previous year. The party had faced extinction, but Charlie Baker somehow saved it. What did it all mean? This piece convinced a lot of people that the party needed someone to write about the soul of the party, and where it was going.
It was in this piece that I started experimenting with pithy quotes about uncomfortable truths. One of my favorites here was: "In 2012, the defeat of former Governor Mitt Romney, Senator Scott Brown, and Richard Tisei was so devastating, that only Republicans could have missed the implications."
A Gathering in the Blue Wilderness (April 2018)
I wrote this 4,800-word piece right before the 2018 MassGOP Convention to show that while Charlie Baker was firmly in control of his party, he wasn't influencing its thinking that much. I predicted that the anti-Baker part of the party would make itself heard at the convention, and it certainly did. This essay led to three media appearances right after the convention.
Identity Crisis: Baker, Trump, and the MassGOP (July 2017)
Having not enough time to get a "year two" update piece out about Charlie Baker, I waited a few months, and then wrote a piece about how Donald Trump was warping the Massachusetts Republican Party in a way that could create a problem for Governor Baker. The piece caught the attention of Adam Reilly of WGBH, who interviewed me for a Greater Boston TV episode on whether an unhappy, Trump-supporting base could cause problems for Charlie Baker.
Dear Rockport GOP (March 2015)
Surprisingly, my second-most popular essay was how the Town Committee system has failed. This is the legal organizational structure for how that people organize at the town and city ward level to support the MassGOP. It gained a wide audience inside the party, many of whom have doubted the RTC system, but never had the language to say why. But also, other pundits in Massachusetts politics said the piece was insightful.