I recently had the chance to sit down with Larry Gillis and talk about his journey, from growing up just outside Boston to serving in the U.S. Army, practicing criminal law, teaching future legal professionals, and eventually finding his way to libertarianism later in life. Larry brings a depth of experience that’s increasingly rare, and his political perspective comes not from theory, but from decades of lived experience.

Talking with Larry was a good reminder that libertarianism isn’t always discovered through slogans or ideology. Often, it’s something people arrive at over time, through observation, experience, and a willingness to question institutions up close. I’m grateful to Larry for sharing his story and for his continued contributions to the Libertarian Party of Florida. Below is our conversation.

You have a remarkably rich background, from Andover to Harvard to Boston University School of Law. Can you tell us about your early life and how those formative years shaped your worldview?

Thanks. I was born and raised in an ethnic neighborhood just north of Boston (Beachmont, in Revere). My father was the local chief of police. Virtually all of my uncles were police officers. Unsurprisingly, my brother became a state trooper some years later. (He later became a criminal lawyer). I went to the same elementary school that my mother had 25 years before. My mother's family, the Kelley family, lived in several houses in the same neighborhood, just up the street.

One of my best friends, virtually the only Protestant in my neighborhood, said one day that he was applying to Andover, of which we had never heard. My father made further inquiries that same afternoon, and my completed application was in their admissions office the morning of the next business day; when he made up his mind to do something, it happened quickly. I was admitted, my friend was not. My father said it would be a good thing to do. It was. When I arrived, instead of being one of the smartest kids at my elementary school, I was easily outclassed by a lot of very serious kids from Manhattan, who had stepped out of their Daddies' limousines on the first day, sharp as razors and ready to do battle. They were already reading the NY Times at breakfast. By way of comparison, at that point in my life, “My Weekly Reader” and “The Readers’ Digest” were my regulars. Little did I know.

There is an old Irish saying, "Root, hog, or die", meaning that you must claw furiously every day for the rest of your life, or you will die. It is based deeply in the Irish experience over the centuries.

This saying has served me well. It certainly saved my bacon during those next four years. That is not to say that I did not enjoy those four years, because there were many opportunities outside the classroom, ones that I took advantage of. Being the undefeated captain of the varsity boxing team was my proudest accomplishment. Getting an advanced placement in French my fourth year was also satisfying, because my abysmal grade in French during my first year had almost caused me to get kicked out. At the end of the first term, I was 121 out of 126 students, academically. The four guys behind me didn’t make it to the end of the first year.

So, for college admissions purposes anyway, I did not appear to be a nerd, but as someone "well-rounded", which was apparently what they were looking for. (I mean, a French-speaking boxing captain at the fancy school, from a family full of cops? What’s not to like?) I got in.

So— not to put too fine a point on it — Harvard contacted me, not the other way around, and said that I would be admitted if I applied. That was a no-brainer. I applied to one college, Harvard.

While at Harvard, I participated in the Army ROTC program and was commissioned. After graduation, I went into the Army. I went to Fort Gordon, Georgia for military police officer training. Later that year, President Johnson announced a major military commitment to Vietnam. After serving three years, I went to law school in Boston.

At that point in my life, I was largely apolitical. I simply dealt with things as they came along. Later, being the parent of four kids, I started to try to get some context, some worldview. It is commonly said that parents raise kids. Frankly, I think that kids raise parents.

You served in the U.S. Army during a pivotal era in American history. How did your military service influence your views on government, liberty, and personal responsibility?

After I got out of the Army in June 1967, I spent that summer visiting Europe by Eurail pass. Then I returned to Boston and attended law school at Boston University School of Law.

At that point in my life, I had a remarkably admiring view of government and policing. I certainly had no philosophical objections to the use of government to address perceived societal problems. However, I had read “Animal Farm”, “1984”, and— most disturbingly — “Lord of the Flies”. From these, I began developing a distrust of government and a profound fear of mobs of human beings. It took a long time, but those three books started me on a trajectory toward Libertarianism.

You later became a State Representative in New Hampshire and served as a prosecutor. What experiences from those roles most shaped your philosophy about government and justice?

Those were all a long time ago. I didn’t join the Libertarian Party until 2014.

I ran for State Representative largely as a way of becoming better known in my community. I ran as a Democrat in a largely Republican area and expected to lose. Because it was a multi-member district, I squeaked in.

I served on the Appropriations Committee and chaired the justice subcommittee. The demands of the role effectively destroyed my law practice, and I did not seek reelection.

Later, through years of criminal practice and prosecutorial work at the district court level, I came to appreciate that defendants were simply dealing with life as human beings, playing the hand they were dealt, and not doing a very good job of it. I did not think any less of them for that. I still don’t. That attitude serves me well as a member of the Libertarian Party.

When did you first encounter libertarian ideas, and what drew you to the Libertarian Party?

After Walter Mondale became the Democratic nominee, I changed my party registration because I was deeply offended by identity politics and political correctness enforced by government decree. Eventually, I discovered that Republicans were not much better.

I was attracted to the “wild West” aspect of libertarian politics. Here, at long last, was a party that simply said, “Let it all hang out.”

Law school and the Socratic Method profoundly influenced my thinking. I demand rigorous examination of facts before reaching decisions. I really dislike shooting from the hip.

You emphasize personal responsibility and volunteerism. Was there a moment that crystallized this belief for you?

It was gradual. It finally dawned on me that solutions cannot be prescriptive. They must come from within the individual, the ultimate sovereign.

Besides, there is a preposterous probability that if allowed, government will prescribe the solution and get it wrong anyway.

Were there thinkers or individuals who influenced you?

Attorney Tom Regnier spoke at an LPF convention and was profoundly persuasive. He later died much too early from Covid. He is missed.

If I had any heroes, Socrates would be among them.

How have your professional skills shaped your advocacy for liberty today?

Anyone speaking on behalf of libertarianism should engage in keen analysis and zealous advocacy. You don’t have to be a lawyer to do that.

How can people use their own backgrounds to advance liberty?

Use your skill sets. Know your place. Put the menu in front of people, explain the choices, maybe make a recommendation, and step back.

How do you view compromise in politics?

There is nothing in it for libertarians. All we do is bargain away pieces of the farm, one principle at a time.

As a Director at Large and Communications Committee member, what are your priorities?

I am largely reactive. I look at the platforms, hold them up against proposals, and act accordingly. I participate regularly in FloridaPolitics discussions and post links to the LPF bulletin board.

What challenges and opportunities does LPF face?

Membership size and funding. Younger voters are dissatisfied with legacy parties. Our message should resonate.

What advice would you give younger libertarians?

Read the platforms. Develop short-form advocacy skills. There is real satisfaction in seeing your name in print.

What legacy do you hope to leave?

I am curating a collection of my libertarian writings as “Pithy Pronouncements.”

Tell us about your current teaching work.

I teach Criminal Law and Procedures at the University of Maryland Global Campus. Any justice achieved is achieved by the parties themselves. If that isn’t libertarian, what is?

I will also be teaching “Libertarianism 101” on site at Florida Gulf Coast University in January.

Where can readers learn more?

Google “University of Maryland Global Campus legal studies”.

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Author’s note: In addition to his work with the Libertarian Party of Florida, Larry continues to teach and engage the public through academic and community programs. In January 2026, he will be teaching a course through the FGCU Academy titled Libertarianism 101: Freedom and Responsibility in Florida and America. The class will take place on January 15, 2026, at The Collaboratory in downtown Fort Myers.