Generations of Staples High School students knew Dick Leonard as a gifted, demanding, yet very kind and caring English teacher.

He began in 1956 and retired in 1995. His career spanned the final years of the school on Riverside Avenue, the opening of the new North Avenue campus, and the “modernization” that tied nine separate buildings into one. It started with traditional “great books” courses, weaved through the convulsive 1960s and

’70s when the counterculture shook education to its core, then reversed course again with a push toward standardization.

Mr. Leonard — who moved to Westport as a teenager (though he commuted by train back to his old school, St. John’s Prep, every day) — saw this town change.

He was here as the post-war baby boomers came of age, and flooded Staples with huge numbers and even greater energy. He was here as the school population contracted, and staff members were let go.

He was here when the education budget soared, and Westporters paid for new buildings, new teachers, new programs, new technology. He was here when Taxwatchers — and yes, that should be capitalized, for they were an actual political party — forced referendums on educations budgets.

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Dan Woog

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Dick Leonard saw it all. Calmly yet passionately, he worked at his craft. As a senior at Staples in the 1970s, I was fortunate enough to be in his AP English class. We analyzed his favorite book — “Let Us Now Praise Famous Men,” James Agee and Walker Evans’ homage to good, hard-working Americans caught up in the Great Depression.

He led — but sat back and enjoyed — rigorous intellectual debates about literature and life. (One of my classmates, Cathleen Schine, has gone on to become a leading American writer. She too remembers that course well.) We wrote in-depth, trenchant author papers. (Mine was on Richard Wright.)

With the self-indulgence of a teenager, I did not realize then that Mr. Leonard was far more than “just” an English teacher. As I got to know him and his family later, as friends, I understood just how remarkable a man he was.

For 20 years, Mr. Leonard served as Westport Education Association president. As a union leader he was heavily involved in contract negotiations.

Salaries, benefits, working conditions — all were on the table, and all were contentious. Mr. Leonard was a fierce advocate for his members, and the work he did to attract, retain and adequately compensate hundreds of teachers from kindergarten through high school helped cement the Westport school district as one of the finest in the country.

Mr. Leonard was a tough negotiator. And it was those bargaining sessions that impelled him to go back to school.

He took law classes at night, and in 1982 earned his law degree from the University of Bridgeport. That made him an even more formidable WEA president, and helped him bring another level of insights to the classroom.

I knew him as an AP English teacher. But he taught all levels — including the anything-goes “Experimental English” — and when the alternatives program was launched in the 1970s, he was an eager participant.

That novel, multipronged program reached out to disaffected students. It was intense and personal, and Mr. Leonard helped make it the interdisciplinary, get-them-to-graduate success it was.

He was involved too in Project Concern. Throughout the ’70s, that program brought under-served students from Bridgeport to Westport. It cost money, and it was controversial. But Mr. Leonard believed in it — and believed it was right for that city, and this town.

While all this was going on, he and his wife Paula raised five children. This was back in the day when teachers could afford to live in Westport. (Her work as a real estate agent helped.) The entire Leonard family was deeply embedded in Westport life. Dick and Paula instilled the values of community service, and giving back, in all five kids.

Westporters may know some of them. Anne Hardy moved back to town 17 years ago, and is active in many organizations. Rick is a longtime Westporter too. Both Anne and Rick’s kids graduated from Staples. Carey Leonard teaches in town. (Another son, Jim, also went into education. He’s head of school at New Mexico’s Santa Fe Prep.)

Remarkably, though, teaching was not Dick Leonard’s first career. Trained as a Navy pilot in the 1950s, he took a job with TWA. But shuttling planes from La Guardia to Idlewild (now Kennedy International Airport), he realized he much preferred working with people, not machines.

It was a fortuitous decision, for countless generations of Westporters.

Dick Leonard died last week. He was 88 years old. I am sure all who knew him join me in now praising this great, good and truly remarkable man.

Dan Woog is a Westport writer, and his “Woog's World” appears each Friday. He can be reached at dwoog@optonline.net. His personal blog is danwoog06880.com.