Tag Archives: Dick Leonard

Dick Leonard Memorial Service Set For June 3

A memorial service for Dick Leonard — the legendary Staples High School English teacher who died earlier this month — will be held Sunday, June 3, at 2 p.m. at Town Hall. The public is invited to attend.

To read more about his life, click here.

Dick Leonard

Remembering Dick Leonard

Dick Leonard — a beloved English teacher at Staples High School, who continued educating long after he retired — died early today. He was 88.

Dick was also a Westport Education Association president, attorney, husband of a Staples graduate, and father of 5 Staples grads.

He approached life as an adventure, even a competition —in the best sense of that word, “to strive together” — and inspired all through his example.

Dick Leonard

The youngest of 4 sons and a Brooklyn native, he attended St. John’s Prep and was in the first graduating class from Fairfield University.

Dick served as a Navy pilot in the mid-1950’s. After a brief stint flying for TWA, he decided he preferred people to machines and became a teacher.

He spent over 4 decades teaching several generations of Westport teens to write with purpose and clarity, and appreciate the beauty of literature. His favorite book was Let Us Now Praise Famous Men by James Agee and Walker Evans, as it underscores the dignity of each person.

Dick met students where they were, capable of challenging those in AP English and participating in a novel interdisciplinary program, Alternatives, with colleagues in the mid-1970’s to engage some of the more disaffected Staples students.

As president of the WEA for 20 years, Dick led the effort to attract, retain and adequately compensate Westport teachers, helping make this school system one of the finest in the country. His skill as a negotiator on behalf of teachers was legendary.

Dick Leonard, as Westport Education Association president.

Dick was also a central figure in efforts in the early 1970’s to bring greater opportunity to underserved students from Bridgeport through Project Concern.

Always up for a new intellectual challenge, Dick returned to school at night and received his JD from the University of Bridgeport Law School in 1982. This proved invaluable during labor negotiations.

In retirement, Dick led short story discussion seminars with small groups in private homes, the Westport Library, Senior Center, the porch at the Abenakee Club, and most recently at Atria, Darien.

Dick worked hard, and creatively, to provide for his family. A natural salesman, his summer jobs included selling World Book Encyclopedias and getting his real estate license. Dick was a lifelong athlete, from stickball on the streets of Flatbush as a kid to baseball, boxing (and later softball) as a young adult, to golf, squash and finally tennis — his greatest love, and a sport he played vigorously into his late 70’s.

Dick and Paula introduced his family to Biddeford Pool, Maine, in the summer of 1974. In 1997 Dick and Paula built a second home there, which continues to serve as a family gathering spot for summer fun.

Dick and Paula Leonard’s grandson Ned Hardy graduated from Staples High School in 2013. They posed in the courtyard of the “new” Staples with their daughter Anne — Ned’s mom.

His vegetable garden was important too. Tomatoes were his specialty, as a boy in his Victory Garden in Brooklyn and later in full splendor on Ludlow Road and Orchard Lane.

He is survived by Paula, his 5 children, and 11 grandchildren: Rick and Amy Leonard (Lizzie, Charlie); Jim and Story Leonard (Kelsey, Molly, Campbell); Anne and Jim Hardy (Will and Ned); Carey and Cheryl Leonard (Amanda), and Colin and Kadie Leonard (Megan, Annie, and Sophie).

A memorial service will be held Sunday, June 3, 2 p.m. at Town Hall. In lieu of flowers, donations can be made in Dick’s name to the Westport Library (20 Jesup Road, Westport, CT 06880, www.westportlibrary.org).


In 2004, I interviewed Mr. Leonard for my book, Staples High School: 120 Years of A+ Education. He said:

Dick Leonard, Navy pilot.

I got out of the service in December of 1955. I was a Navy pilot, and [Staples principal] Stan Lorenzen had been a World War II officer. He told me he was letting a teacher go.

I taught there from January to June of ’56, then went to work as a pilot for TWA. But I would get up at 3 a.m. to fly a 7-minute flight from LaGuardia to Idlewild. I found I wanted to work with people, not machines, so I returned in 1958.

My first classroom was in a Quonset hut on Riverside Avenue. There were 4 classes between the old and new buildings. I taught there with Wyatt Teubert, Wayne Ross and Ray Tata.

In the spring of ’58 I subbed for Frank Gilmore, who was clerk of the works for the new school. I started full time in September of ’58, the same time the new building opened here. Everything was clean. I had my own classroom – Room 612. I taught 5 periods a day, and no one else shared the room.

I loved the layout of the new school. It was beautiful, with all the walkways leading from building to building. The vista from Building 6 across the fields was great. A lot of parents complained over the years about students going outdoors all the time with their coats, but the kids were pretty accepting.

At the time the English department was led by Gladys Mansir. She was an old-time teacher, who’d had nearly everyone who went through Staples. Then V. Louise Higgins took over. She was a tough, bright gal who really fought hard for English teachers to have four classes. That was a big plus. We could really do a lot with the writing program.

Dick Leonard, in his classroom.

Paperbacks came in in the mid-‘60s. Before that, English was taught like it had been in the ’40s, with different big anthologies for sophomores, juniors and seniors.

In the ’60s we started English 4-E, led by Charlie Raphael, Marue English and Joe Duggan. Rather than us teaching the kids, we said “let’s have the kids tell us what they want to learn.” That was highly controversial. In the ’70s we had more changes. Changes take place every 20 years, regardless of anything else.

[Principal James] Calkins was the best thing that could have happened at the time. He was loose, flexible, and friendly enough so the kids didn’t rebel the way they did at other schools. But the parents eventually thought there was too much looseness. I thought open campus was a good idea, and that it worked out well.

The George Cohan years were a difficult time, with the renovation and all. George was an academician. There was a forward push in English toward electives, led by Joy Walker. Kids could fit in the courses that best fit their needs. There were more courses than just AP, A, B and C. Some kids chose to goof off, but most didn’t.

As for the Jaffe years: I liked Marv. He was an easygoing, flexible principal. I was president of the [teachers’] union, and we got along well.

I taught for a while in the Alternatives program, with Karley Higgins and Frank Corbo. That was before special education – for kids who were unable to be successful in mainstream education. We had up to 75 kids, below Building 6. Then special education grew, and we needed to have smaller classes for those kids.

By the time I retired in ’95 we’d gone from a small school to a big one, and back to small. But we always had a faculty that was professional and academic-oriented. The school became more of a closed place after renovation, though, and less aesthetically pleasing.

Staples has always been a “lighthouse.” It was an important place even for parents of younger kids, who weren’t yet in high school. There’s always been strong support for education in Westport, and it’s even stronger now because of the number of parents with young kids in town. The Taxwatchers [a group devoted to lowering taxes, with a particular emphasis on education budgets] seem to have disappeared.

Staples was, and still is, a special school. I think it’s because of the kids we have, and their parents. Everyone aspires to be the best they can. And the faculty is bright and hard-working.

I’ve certainly changed. I came from a very conservative Irish Catholic background. I moved to Westport after my junior year in high school, and commuted as a senior back to St. John’s Prep in Brooklyn. I started out as a fairly rigid teacher, but I became much more flexible, more able to recognize individual differences in kids.

It’s funny. Last year, I came back to fill in for two 2A classes. We did Araby by James Joyce. But instead of writing essays for the final, we talked for two hours about the personal experiences of infatuation, unrequited love, and life as teenagers. They said it was the best exam they ever had. You couldn’t have done that in a lot of other schools, but that’s the way education really should be.

Proud veteran Dick Leonard, in Westport’s Memorial Day parade.