Knowing His Case Better Than Anyone

(above) Teddy McNaught in 1994—when he earned the William Knapp Morrison Award at Commencement—and in 2023.

Teddy McNaught ’94 Reflects on Learning to Take a Hit and Keep Going

Teddy McNaught remembers many moments in his educational journey and early career that could have broken him. The hard-learned lessons, however, not only made him more resilient, they also made him more empathetic to the people he represents.

“Attorney McNaught, your argument is actually making it worse for your client,” a judge interjected in a case early in Teddy McNaught’s legal career.

“Thinking about it now makes me laugh,” says Teddy, “but, at the time, it wasn’t funny. All defense attorneys experience humiliation at some point. Fortunately for me, it wasn’t the first time, and it didn’t break me. I had felt it before, and I knew I would be okay—in fact, better for it.”

Teddy McNaught came to Cardigan for eighth grade in the fall of 1992. He was 14 years old, away from home for the first time, and surrounded by kids who were able to challenge him at everything. Being away at that age forced him to develop a kind of independence that most kids don’t develop until college. And he learned quickly how to solve his own problems.

“I got in a fight with my roommate in probably the first week of school,” he says. “We were two hard-headed kids in a small, shared space, and we clashed. I did not win that fight. And that could have been the end for us, but it wasn’t. We were teammates in the winter. We had to figure out how to get along, and that’s what we did. We even chose to room together the next year.”

Teddy also recounts receiving a grade of A4 in typing class. (In the ’90s the effort scale was inverted, so by today’s metrics that would equate to an A2—high achievement but abysmal effort.) Typing wasn’t a big deal for Teddy, but the grade had big consequences, keeping him off honor roll and denying him some privileges. It was a wake-up call.
 

That’s what failure at Cardigan looked like: not shame, not damnation, but an opportunity to learn. We were accountable, took responsibility, and we were better for it. Teddy McNaught ’94

“There’s a pride in figuring things out and solving your own problems,” Teddy says as he reflects on being allowed to struggle and flounder and face the consequences.

And it wasn’t just in academics. He remembers taking a penalty shot in a hockey game against some of his old teammates from Maine. To add a bit of drama to his moment, Teddy took a couple laps around the circle before collecting the puck and scoring. He thought it was an amazing performance, just like Rob Lowe’s character in Youngblood. Coach Andy Noel P’16,’19, however, did not and gave Teddy some very direct feedback about what would happen if he ever saw showboating like that again.

“It was good feedback. Coach Noel was right,” Teddy admits. “True pros don’t act like that. That’s what failure at Cardigan looked like: not shame, not damnation, but an opportunity to learn. We were accountable, took responsibility, and we were better for it.”

And he was. By the end of his Cardigan career, Teddy was a varsity athlete, and he made his way back onto the honor roll. He was a student leader and member of NJHS, Green Key, Glee Club, and student senate, and he got into his top choice secondary school, St. Paul’s, where he continued to excel.

His future was bright, until a bad decision during his senior year led him to withdraw in the middle of the college application process. All of his top college choices rejected him, changing the course of his life. But it’s part of his story and made him who he is today, which is, if anything, a more credible, relatable, and empathetic defense attorney.

“People don’t call me when things are going well,” he says. “They call when they’ve messed up badly. When lives are coming apart and they’re looking for someone who can help them hold it together, I am effective in part because I understand firsthand that people make mistakes and sometimes those mistakes are big.”

When thinking about failure, the tired truism “If at first you don’t succeed…” comes to mind, but in the courtroom, the second half of the adage “try, try again,” doesn’t really apply. An adverse verdict is difficult to undo. “I lost my first three jury trials, 1, 2, 3 guilty, guilty, guilty, and I was in a pretty dark place,” he says. “They were small cases but just devastating to a new defense attorney. That said, they revealed to me so many things that I didn’t understand about the process, and through that, I began to find my own voice in the courtroom. Nothing is more persuasive than authenticity.”

Fast forward to today, Teddy and his team try to get their failures in before trial. They test different strategies, examining a case from every angle. Fellow attorneys are invited to pick his theories apart. Those pre-trial “losses” are ultimately what help him build the best cases. He continues, elaborating on gaining experience, maturity, and credibility in front of the judge and jury: “Plus, there is no such thing as being over-prepared. You have to know your case better than anyone. If you establish yourself as the person in the room who knows the most, the audience (jury or judge) will be more inclined to trust you. From that knowledge, gained through preparation, you can argue with confidence while still being humble.
 

But at Cardigan, even in the early ’90s, there was space to mess up, to push boundaries and come back from it. We weren’t perfect kids. We fought, we tested rules, we got in trouble. But we also learned to apologize, to forgive, to grow. I didn’t know then how foundational those moments would be. I just knew I was learning. Teddy McNaught ’94

Still, some rulings just do not go the way Teddy hopes or expects.

“It can take an emotional toll,” he admits, “but experienced lawyers understand that losing is part of the job. If I know that I have done everything I possibly can, then I can sleep at night…There is no such thing as a perfect trial. Even when I win, I will replay the case in my head and find things I wish I had done differently.”

Now, as a father as well as a lawyer, Teddy thinks about this all the time. “How do we raise kids who can take a hit and keep going? How do we raise professionals who don’t crumble when things go sideways?”

The answer, he thinks, starts young at places like Cardigan, where failure isn’t feared but folded into the fabric of the education—where faculty like Andy Noel can call you out for peacocking on the ice and still make you feel like you belong. Where a bad grade isn’t a sentence—it’s a signal.

“Society today doesn’t leave a lot of room for failure,” Teddy says. “Kids are monitored, optimized, tracked toward outcomes. Risk-taking is discouraged. But at Cardigan, even in the early ’90s, there was space to mess up, to push boundaries and come back from it. We weren’t perfect kids. We fought, we tested rules, we got in trouble. But we also learned to apologize, to forgive, to grow. I didn’t know then how foundational those moments would be. I just knew I was learning.”

And so, armed with what he proudly calls a “body of failure,” and more “experience” as he gestures toward some gray hair coming in, when someone walks into his office thinking their life is over, Teddy responds truthfully saying, “You’re going to be okay. I’m going to help you.”

Today Teddy runs a successful criminal defense practice in Boston’s North Shore. He started his career in law working as a clerk, paralegal, and investigator, began practicing in 2010, and opened his own firm, Edward A. McNaught III, P.C., in 2014. He received his BA from St. Anselm’s College and his JD from Suffolk University Law School. He has litigated cases in Juvenile, District, Superior, and Federal Court, and he sits on the Board of Directors for the Essex County Bar Association.

This article was originally published in the summer 2025 issue of the Cardigan Chronicle