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,


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.

37 responses to “Remembering Dick Leonard

  1. Eric William Buchroeder SHS '70

    I never had Mr. Leonard but enjoyed his company and friendliness to me as a student. He was larger than life having been successful in at least three careers any one of which would have been a huge accomplishment by itself. My recollection is that the English and History departments, both of which I enjoyed, were populated by some fantastic teaching talent and I think Mr. Leonard was right at the top. Westport was lucky that he preferred teaching above the many other fields he had mastered.

  2. Dick was a wonderful neighbor and a positive force in Westport. Our condolences to Paula and the family.
    Lou and Joan Mall

  3. Peter Hirst

    One of my favorite teachers ever. First one ever to encourage my poetry, when I needed it most. Let me do my Author Paper on Kerouac, when a lot of teachers wouldn’t have. Thanks, Mr Leonard.

  4. Arline Gertzoff

    The best and the brightest A true Staples icon.
    Rest in peace

  5. Dave Eason

    I am so so sorry to hear this. What a guy! Old school and a true Staples icon indeed. RIP Dick…

  6. Dolores Bacharach

    I am blessed to be able to call Dick and Paula long time friends of the Bacharach family. Dick was a gentleman and a gentle man. He told wonderful stories. He had such affection and respect for his students. About the tomato plants…not just the desire for a good tasting one, but a creative opportunity to get down in the dirt and work with his hands. The fact he and his friend had a competition for the first ripe tomato only added humor and challenge to the enterprise. There was even a Spring, when Dick rigged bags filled with water around each plant to speed the ripening process. He was an all-in kind of fellow. He will be long remembered and equally missed. Sending comfort and peace to all the family.

  7. Michael Brennecke

    I had Dick Leonard I think as a junior. I remember that he thought I’d kind of missed a major point in my author paper. Oh well, that’s why I’m not a writer. Good man though. I did not know what an interesting career path he had. We were lucky it led him here.

  8. Michael Mombello


    This is wonderful. A very special family and some of our dearest, closest friends. You captured it all beautifully.

    Thank you,


    Michael Mombello Realtor & Partner, KMS Partners @ Coldwell Banker 203.505.4477 | | | 472 Riverside Avenue, Westport, CT 06880


  9. Vanessa Bradford

    I had Mr. Leonard for AP English in the 70’s. I had the pleasure of seeing him last year at Atria and what a sweet reunion. I so well remember the book we had studied back in the day by James Agee and Walker Evans . So now let us praise Dick Leonard. He will be missed !


  10. Matt Sappern

    What a sad news item but a great guy to celebrate! When my kids ask me about those few teachers that truly helped shape my thinking, Dick Leonard is always at the top.

    Those of us who studied with him were so fortunate. RIP Mr. Leonard and best wishes for the famy.

  11. Karl Decker

    Enough words have been written now about Dick. Suffice it to say for now, he was a professional advocate, inspired colleague and academic mentor to us all..I was privileged to have learned from him…..His death heralds the end of a great and innovative era at Staples..

    • Werner Liepolt

      April is the cruellest month, breeding
      Lilacs out of the dead land, mixing
      Memory and desire, stirring
      Dull roots with spring rain.
      Winter kept us warm, covering
      Earth in forgetful snow, feeding
      A little life with dried tubers.

      TS Eliot. The Wastland

      Dick knew literature, and I hope his passing has some greater meaning for Westport than merely that a great teacher has died. Dick loved literature, and I believe he knew what precious keys he was offering to those of his students who could seize and use them.

      How frustrating it must have been for him at the end to see politicians constantly fail to make agreed upon payments into the health care and pension benefits he had negotiated in good faith

      But how rewarding and deserved for him to see his family prosper, grow, and add to the community he taught and cherished.

  12. Gerry Kuroghlian

    I was extremely fortunate to have had Dick as my mentor during my first three years at Staples. He was a brilliant teacher, WEA president and attorney who together with Paula raised an amazing set of children. Westport was very fortunate to have had the Leonard family at residents. Heartfelt sympathy to the Leonard family.

  13. Bob Selverstone

    Dick Leonard will always remain in my memory as one of the best examples of teaching at its best. He was a role model for other staff (of which I was a colleague for 25+ years because of his integrity and dignity. He was loved and respected by students and faculty. What extraordinary fortune it was to have him in Westport.

  14. Dale Eyerly Colson

    How blessed those of us fortunate to have Mr. Leonard were. He challenged me, he supported me, he nurtured me and he inspired me. I’m so grateful for the many gifts he gave me that have served me so well ever since my long-ago days at Staples.

  15. K . Spear .

    This is Sad News .. He was a Wonderful teacher , and a Great Guy .
    God Speed Dick Leonard .. See you on the Other Side

  16. Peter Krieg

    My wife, Debbie, and I bumped into Dick and Paula having lunch at Pearl on a beautiful day last summer. As always, they were the world’s happiest couple. Paula, the kids, and about 10,000 former students and fellow teachers will remember him very, very fondly.

  17. Jim Bacharach

    Infectious positive energy. I was so fortunate to experience it as one of his students and doubly so because he was a great friend to my family. Such a multidimensional legacy, My condolences to the most noteworthy–his family.

  18. Tom Feeley Sr

    Good man🇺🇸🙏

  19. Susan Huppi

    I still remember reading Let Us Now Praise Famous Men in Mr.Leonard ‘s English class. I have found memories of my years at Staples and loved the emphasis on learning and the open campus. Mr.Leonard and other dedicated Westport teachers helped inspire me to become a teacher myself. Mr.Leonard you will be missed!

  20. Bill Boyd (Staples '66)

    Another great tribute! I didn’t have Dick Leonard as a teacher but I got to know him later at law school…a wonderful man who gave of himself so generously…..all who knew him had their lives wonderfully enriched….
    R I P Dick….

  21. I remember Dick Leonard with fondness, but had no idea he was so accomplished! Thanks for the tribute, Dan.
    I know you two were very close.

  22. Mr.Leonard taught me how to read and write critically. He was a wonderful teacher – kind, inspiringand creative. I still use so many of the techniques he taught us for our senior Author Paper. The late sixties were nuts, but he was calm and sane and warm and so smart.

  23. 35 years later, my copy of Let Us Now Praise Famous Men is still on my bookshelf. Thank you, Mr. Leonard!

  24. Bobbi Essagof

    I never actually met Dick but worked with Carey, Anne, Ned and Will at GFS. Clearly all products of this wonderful man. I am sorry for your loss. He will be watching all you do with pride.

  25. Deb Holliday Kintigh, Staples '64

    WOW, 54 years since my senior year when I sat in the front row of his English class (drawn to that spot by his electric blue eyes, I must admit)! Mr. Leonard was generous with his time, guidance and advice and encouraged us to think critically and celebrated our successes. Thank you, Mr. Leonard, you made a lasting impression!

  26. John Siddell

    Great man, great Westporter, great family…my condolences to the Leonard family, RIP!!

  27. Rose Daily

    Dick was a Gentlemaen, in all aspects of his life
    He loved people and held a high standard for us all.
    I have 2 fond memories of Dick that jump out when I think over his contributions to the town and to education.
    At Staples High Faculty Follies,Dick was brave enough to sing a solo accompanied by staff.He practiced and did his best He enjoyed every minute of this brief off off Broadway experience
    In Maine, during the summer, Paula and Dick provided all visitors laughter, and love
    I always admired his stand for us teachers and his professionalism in all negotiations.
    I send my regrets for their loss to his family and will remember him as a very Good Man

  28. Joyce Eldh

    Great write up, Dan, for an obviously great man. I didn’t know Dick but your article allowed me some greatly insight. Dick not only impacted students but his impact is seen in his lovely children and their extended families – all giving and dedicated individuals.

  29. Carl Leaman

    proud to say that Dick Leonard was my friend

  30. Charlie Taylor

    God Bless Mr. Leonard. He took a dislocatedand dyslexic kid from Western Kentucky and welcomed me into his English class as a sophomore. He told me I could four.
    That all I needed to hear. He challenged us, rewarded our curiosity and led us to think for our selves. Rest In Peace

  31. Kerstin Rao

    Dick Leonard was involved in the early days of WestportREADS, and brought insight and humor to our book selection as well as ideas for events related to the book. He was always warm, witty, and hard-working. Sending his family my condolences – what a legacy he has inspired!

  32. Blessings on Dick and his family. He was totally involved and was a devoted Union member, as well as a totally devoted teacher and mentor. He will be missed.

  33. Richard Sauvageau

    Many of us retirees are so grateful to Dick. His leadership in the WEA has allowed most of to enjoy a comfortable retirement. He made a difference while we were employed and we continue to reap rewards in retirement. Thanks Dick, you made a difference to kids and to teachers.

  34. Melody James

    I’m so sad to hear this news. I had Mr. Leonard for Senior year English and really loved his class; over the years would bump into him; terrific teacher and inspiring life. My thoughts are with his wife and children.

  35. Tim Wright

    I admired Dick from the moment I met him, early in my first year teaching in Westport, 1973. Dick was one teacher of the several I admired from the distance between Coleytown Middle School and Staples. Didn’t know him well, but I recall clearly his friendly warmth, his commitment both to education as force and value and to the worthiness of teaching professionals.

  36. Richard Bourke

    I had Mr.Leonard for AP English my senior year (63-64), and he instilled in me a lifelong love for reading and writing. One of the few HS teachers whose teaching I vividly recall with reverence and fondness