Meet Stafford Thomas: Staples’ New Principal

Stafford Thomas’ life is filled with intriguing twists and turns.

But if Stanford University had not lost his grad school application, he might never have ended up at Brown — and gone into education.

And he undoubtedly would not have landed in Westport, where he is just settling in as Staples High School’s new principal.

Thomas spoke easily and at length the other day about the journey that brought him from St. Croix to North Avenue. He’s got plenty of time to figure out where he’ll take Staples — he’s just starting to meet with administrators and staff members, and students don’t return until late August — but much of what he’s done in his life had led to this point.

Even if he didn’t realize it as it happened.

Stafford Thomas, with an autographed photo of Don Mattingly.

Thomas’ mother taught reading in the Virgin Islands, through the Vista national service program. That’s where she met his father, a native of Dominica who ran a driving school. (“I got behind the wheel of a car when I was 5,” Thomas laughs. “And alone at 8.”)

His mother moved back to the States to teach in a private school. Thomas spent his tween and teen years in Manhattan, Queens and Long Island.

Georgetown University wanted him for football. But he was used to getting up at 3:30 a.m. to work construction, so he switched to crew (and early morning rowing practices) there.

After a study abroad year in Florence, Thomas interned on Capitol Hill for the non-voting congressional representative from the US Virgin Islands.

Many Georgetown grads were going into consulting. Thomas did not see himself on that path. His mother — a career teacher — advised him not to go into education. He applied to Stanford’s graduate school for public policy. But he also applied to Brown’s Master of Arts in Teaching program.

Stanford misplaced his forms. So 2 weeks after graduation, Thomas was in Providence. Part of his coursework included teaching and coaching basketball at Lincoln School, a private institution for girls.

Stafford Thomas addressed the Board of Education last month, after his appointment as Staples High School’s new principal.

That Brown degree led to a job at South Side High School in Rockville Centre, New York. The staff was young, and he was mentored well.

The next steps in Thomas’ professional development included a dual program at Boston College. He took law classes during the day, and studied educational leadership at night. Highlights included studying the achievement gap in Brookline public schools, a practicum with the principal of a K-8 Catholic school, and a stint at a Shanghai teachers college.

“I was busy,” Thomas says with understatement.

His new degrees led to a position as associate director of policy for Providence mayor (now Rhode Island congressman) David Cicciline. A chance meeting there led to an offer to work with a renowned principal at Barrington Middle School.

Thomas was all of 26 years old.

He learned leadership skills there, and at 30 was handed more responsibilities as an administrator at Mystic Middle School. He worked with talented department heads, and helped start unified arts and sports programs.

Staples principal Stafford Thomas shows off his Wrecker hat.

Eight years ago, Hillcrest Middle School in Trumbull hired Thomas as principal.

This year, the Connecticut Association of Schools honored it as Middle School of the Year. The award noted that students, faculty, administrators and parents combined to create a community known for innovative teaching strategies, after-school programs and high academic achievement.

Middle school, Thomas notes, is often a difficult time for tweens and young teenagers. His goal was to make the school comfortable (“like a family”) for students, staff and parents. He made sure that staff members went beyond simply knowing students. “Connections are so important,” he says. “It’s all about communication and openness.”

Thomas brings those experiences — as a team leader, communicator and innovator — to Staples. “I can’t imagine a better position in secondary school administration anywhere,” he says.

His new school is esteemed for its academic, art, athletic and extracurricular achievements. But pressures are strong. With students spending their final 4 years there (and at home) before heading into the real world, there’s plenty of emotion and uncertainty. Thomas is mindful of the need to make high school a comfortable, welcoming place for all.

“This is a home away from home, for students and staff,” he says. “We can’t control everything. But we can control what goes on here. We can do all we can to make this a positive, happy time.”

After his appointment was announced, Stafford Thomas met with staff members who came to the high school to welcome their new boss.

He’ll spend this summer meeting with administrators, staff and community members. He’ll ask what works for them, what’s needed, and how he can support them.

(He’ll also spend time with his wife — a kindergarten teacher in Trumbull — and 3 1/2-year-old son. He’s an avid tennis player, and just stopped playing softball.)

“The field of education is about people,” Thomas says. “Communication and transparency are big components of dealing with people. From there, you get to a position of trust.

“Everyone may not agree with every decision. But people need to know how a decision was made. That’s worked well for me in the past.”

He’s been in Westport just a few days. But he knows the town’s expectations are high. “People here want the best for everything — including education. They support the budget, the programs, the facilities. We owe it to them to give them the best.”

Everyone at Staples should have high expectations too, he says. “I’m glad that’s where we are. We should be on the cutting edge. I look forward to all the support and passion. People are very positive.”

Stafford Thomas is too.

And in August, the Staples community will be positively excited to welcome their principal to his new home.