Michael Romano S’89: A New Paradigm for a More Just World
How lessons from TMS inspired Michael Romano to move beyond conventional wisdom in criminal justice reform
Michael Romano is a lawyer specializing in criminal justice reform and teaches at Stanford Law School. Michael founded and directs the Three Strikes Project and teaches criminal justice policy and advanced criminal litigation. In 2019 he was appointed by Gavin Newsom as inaugural chair of the California Committee on the Revision of the Penal Code and was principal author of the Three Strikes Reform Act (Proposition 36), one of the country’s first criminal justice reform initiatives, which led to the release of over 3,000 people serving life sentences for non-serious, non-violent crimes.
With his students, Michael represents incarcerated people in state and federal courts and has won the reversal of over 200 life sentences. His work has been profiled in The New York Times Magazine, Rolling Stone, The Economist, and the award-winning PBS documentary The Return.
Lucretia Penfield (TMS’s Director of Admissions, Enrollment, and Financial Aid) chatted with Michael to learn about what brought him to the Mountain School and how the spirit of “reaching beyond the self to the common good” has informed his career.
“The biggest takeaway lesson [at TMS] was to identify paradigms and remember that they are breakable, especially when there is an obvious benefit on the other side. The obvious benefit on the other side is bringing justice to an area of criminal law where at least one generation had shrugged their shoulders and said, ‘This is just the way things have to be.’”
How did you decide to attend the Mountain School?
I was coming from Collegiate School in New York, and the Mountain School was pretty new when I was considering applying. I grew up skiing a lot in Vermont and I had a cousin who was at Middlebury, so I had some sense of what Vermont was like. I associated it with ski culture… but I didn’t do one day of skiing while I was at the Mountain School.
Before I arrived I had a total misunderstanding of what TMS was about. I thought I would live in Vermont, and go schussing downhill skiing at resorts. I was totally unprepared for what it ended up being… in the best way possible. It not only changed my life but changed my perspective on school, on life priorities, on relationships.
How did you turn the corner from expecting to downhill ski every day to embracing the farm, woods, and community elements of TMS?
I remember the morning chore of having to feed the sheep in the morning. It was 10 degrees below zero, dark and windy and cold and there were no lambs yet. I was walking from Underwood all the way down to the sheep barn, cracking the ice that had formed on the water buckets with my boots, refilling them, refilling the hay for the cows. These jobs and this type of responsibility were completely foreign to the life I’d lived up to that point, and yet I remember feeling the responsibility of providing food and drink for the animals by myself at some early hour of the morning. From Day 1 I perceived my role in keeping the farm and community together.
At the Mountain School, I felt thrown into the deep end in a way that is still memorable to this day. Cohesive community was the core of the program. The school wasn’t about going to Vermont to have adventures, it was internally focused on what it means to live together. The invitation and the responsibility for each of us students was putting our arms around the whole community.
“Cohesive community was the core of the program. The school wasn’t about going to Vermont to have adventures, it was internally focused on what it means to live together. The invitation and the responsibility for each of us students was putting our arms around the whole community.”
What stayed with you the most from your time here?
The feeling of possibility. I was incredibly impressed that the Mountain School could even exist. I went to a traditional all boys’ high school where there was a very prescribed path to academic success and achievement and even one’s life course. It was a very structured path. TMS blew my mind, in that it was even possible to think outside of that box.
I admired David, Nancy, Jack, and Kevin, and all the original corps of teachers and administrators who decided they could do this. They thought, “Wouldn’t it be fantastic to try to bring high schoolers to a working farm in Vermont?” Despite the fact it had not been done before, they actually pulled it off! That ability to think, “Anything is possible!” and the realization that you do not need to follow a traditional path really opened my mind to possibilities and liberated my idea of what schools could be like, what careers could be like, what learning could be like.
I loved my environmental science class. I loved the journaling part of English class. Part of the experience is that every week the teacher reads an excerpt from someone’s journal, and it’s just magic. I remember feeling like at home, at Collegiate, I was attending a very elite prep school. I expected to be academically overprepared for the Mountain School. But again, it defied my expectation. I remember getting my first graded essay back from Jack and I got a C or a C- on it, a grade I’d never seen before in my life! I was floored by the challenge that he and other teachers put on us to challenge ourselves in a way that we weren’t just following the rote pathways that we had developed in high school as to what makes a good essay.
I thought a lot more critically about my own work– what I was saying and why I was saying it. I was rocked on my heels a little bit, and I doubled down and worked extra hard to correct some of my arrogance and impress my teachers, because I had such close personal relationships with them and I wanted to rise to their expectations. I know this experience made me a better writer. I still think of some of Jack’s writing tips to this day.
How have the perspectives and experiences you got at TMS shaped your career?
I think about that all the time. I’m certain my time at TMS has shaped the work I’ve undertaken and the way I collaborate with others to make change. I’ve spoken to Mountain School alumni who do similar work that I do, and we try to draw the connection, but it’s not obvious to me, even though I sense it deeply.
I remember shortly after the Mountain School I went camping with one of my friends from TMS and he said to me, “So they want us to change the world. But change the world to what?” That question had a profound impact on me.
Obviously the Mountain School has a strong bent toward environmentalism, environmental science, global climate change. But I remember thinking that for me, I learned more lessons in critical thinking, in re-examining conventional wisdom. Those were the broader lessons that I took away from TMS.
A lot of my work today is challenging the way that our justice system works. There is a lot of conventional wisdom and conventional thinking, not only publicly, but even amongst progressive activists. I think my main contribution to the field is to have not accepted the conventional strategies and approaches to certain types of cases, not accepting injustices, thinking a little differently and a little outside the box. Many of the decisions I’ve been able to help overturn were achieved by taking an idea from one place in the law and applying it to another.
Looking back, it seems ridiculous to start a high school in Vermont on a farm from a prep school in Boston. But then the founders of TMS said, “Well, why not? It’ll be wonderful.” And similarly, there is something about the strategies that we’ve been able to implement in my program, we approach our cases with a spirit of questioning and moving beyond the “just because” answer. In fact, when you show people what’s going on there’s a lot of empathy and understanding and you can change the world.
People want to be just, they want to see the world as a better place, they just have to be shown that path. TMS is a place where you can break paradigms. I learned the whole idea of paradigm at the Mountain School. I remember reading Zen and the Art of Motorcycle Maintenance and The Power of Myth. The biggest takeaway lesson was to identify paradigms and remember that they are breakable, especially when there is an obvious benefit on the other side. The obvious benefit on the other side is bringing justice to an area of criminal law where at least one generation had shrugged their shoulders and said, “This is just the way things have to be.”
You have a child attending TMS this fall. What is a piece of advice you’d give her, or any other students starting at TMS soon?
I’d say to my daughter, “Keep your mind open.”
I hope that my child doesn’t have too many expectations and ideas about the Mountain School, actually. My experience of having no idea what I was walking into was an incredible benefit to me. It was humbling, and it gave me a chance to prove to myself that I could adapt to an environment with different values than the one I’d always known.
It’s kind of impossible to enter a situation nowadays without knowing what you’re getting into, when we have so much access to information. Yet knowing as little as possible can actually be a benefit. To have too many expectations about what it is going to be like might end up being wrong or disappointing.
I hope for my child to be open to exploring new friendships and new ways to engage in a classroom. There is a very “prep school” way of going about high school that intelligent, perceptive kids can feel pressured to follow. Yet I think the Mountain School can challenge this pathway and teach students how to learn differently, especially if they’re coming from an education where there is a very consistent pedagogic approach. Shaking up your idea of what it means to learn is so valuable!
Clearly your work has influenced your daughter Oona’s outlook on the world. (Read Oona’s application essay, reprinted with her permission, below). She wrote about her experiences at the Anti-Recividism Coalition camping trip in the Sierras. How do you think nature contributes to building community, even across lines of difference?
In many ways, the trip reminds me of TMS. With the anti-recidivism stuff, there’s something about spending time in nature together that removes social distinctions and connects us all. It’s pretty special for anyone to spend time in nature with the guys we go with. Many have not been outside of South Central Los Angeles, some do not know how to swim. To see beauty in nature through their eyes is really spectacular. Like at the Mountain School, we come without technology, which allows us to let go of the distraction of life outside. We don’t have tents, we sleep under the stars, just like on the Solo. Everyone participates in the chores that are needed to keep the camp running, and you just do your best at what you’re assigned to, no matter your income or education.
My family has been attending the trip for years. On this most recent trip we started a rafting trip where there was a Class 5 rapid right at the start. We got out of the rafts ahead of time and scoped it out, and then followed the guide’s instructions to hunker down and hang on as the boat got swept into the water. I remember when we went over the rapid, half the paddlers in the boat got flung out and were bobbing in the river. I was left in the boat with these big guys, who have been convicted of horrific crimes including murder, and I remember watching one of them pluck my daughter out of the river and put her back in the boat. The community that type of experience builds is just not possible to explain.
I really do hope that Oona finds her own path, and I believe that the Mountain School can help her break out of what she might think is expected of her. I know that living away from home in and of itself is helpful, and I’m excited for her to have this chance that I did, even though the world today is so different from the world in which I attended TMS.
Oona Romano’s Application Essay
TMS Prompt: Living in community is at the core of what we do. What does community mean to you, and how have you fostered it in your world?
Last summer I left my house in the middle of San Francisco with my brother and father, driving up to the Sierra Nevada foothills. We all carried our phones along with stress from the long work and school weeks. My brother and I had our headphones on, looking at our separate screens while my dad drove in silence. It was early in the morning, and we were headed to the annual Anti-Recidivism Coalition retreat. As the buildings and street lights turned into mountains and trees, we started to forget about our phones that soon we would not be using at all.
We’ve done this every year since I was six years old — spent a weekend with 75 formerly incarcerated people. The idea is simple: just be there, together, and support people as they rebuild and experience joys of their lives that have been postponed by the justice system. I’ve never fit in, really, at least not externally, and this trip it felt especially obvious: I'm a girl and white and small and young. Still, these annual trips have taught me more about community and vulnerability, and how the two are related, more than anything else in my life.
I was happy just to be out of the city. There, my community is built around achievement. Each student at my school wants to have the highest grades. Each kid on my soccer team wants to be the best. We don’t say we’re competing with each other, but we are. It makes me feel like if I am not ahead, I am behind. It can be extremely isolating, my peers in my community are all doing similar things, but we don’t really have a common cause. Strange as it might sound, when I join up with dozens of former gang members, many with tattoos up their necks, who stand feet taller than me and have arms the size of my legs, I relax a little. We’re not competing with each other. We’re just together, making each other laugh and hoping each other succeeds.
On the first night of the retreat, we ate dinner with a 32-year-old man I didn't know. He told us how he started serving time for murder when he was 15 and had just gotten out of prison. He had so much enthusiasm for all the experiences he now cherished now that he was out, ones I had unwittingly overlooked. Although he had never met us before, he was so genuinely invested and vulnerable with us. After it got really dark, he showed us different constellations as we all stared at the same sky that we immutably shared, despite our completely separate life experiences.
The next day we paddled down the American River. In our raft was Jerome, who was 62 who had just lived his first year out of prison for the first time since he was 17. We spent the day balancing each others’ weight in the raft, trusting each other not to screw up on the rapids, laughing, splashing, managing too much gear.
That night, all of us (who were almost all men), tired and sun-struck, sat around a campfire. The night was not about me — far from it. People talked and I just listened. It was magical and transformative. We’d had to trust each other in simple ways during the day and I think that trust allowed people to be open with a mutual destigmatized understanding. People talked about family members getting murdered. People talked about committing murder themselves. People talked about poverty and heartbreak and close relationships they had in their gangs. People talked about how overwhelming it is to re-enter society after being locked away, thrown out, and forgotten about.
I always hope to bring how much those people embraced me despite our differences and the healing feeling of those weekends home with me, but it’s hard to do. Like my friends at home, I want to do well in my classes and win my games. But I also know I’m best when I’m outside all that. Those ARC trips have taught me that community is not made by people doing the same thing and being “good” at it. Community is made by caring and wanting the best for each other.