Richard Leonard of Darien, a longtime Westporter, Staples High School teacher, and 20-year head of the teachers union, died today. He was 88.
Dick Leonard: retired Staples teacher. File photo
He and his wife Paula moved to assisted living in Darien in 2015 after they said they could not find similar housing in Westport.
Leonard, moved with his parents to Westport in 1946. He was just 15 but commuted daily on the 6:30 a.m. train to New York, so he could finish up at St. John’s Prep in Astoria, Queens. Paula Leonard moved with her parents to Westport in 1952, graduating from Staples High School that year.
It wasn’t long before the two met and began dating.
In 1957, after four years as a Navy pilot during the Korean conflict, he and Paula married, settling into their first home on Lone Pine Lane, then Ludlowe Road and eventually Orchard Lane.
They raised five children in town, and all attended the Westport Public Schools.
The school system was integral to the Leonards’ lives. So too was community involvement. He taught English at Staples for 37 years, and for 20 years served as president of the Westport Education Association. He also sat on various ad hoc town committees, and the Westport Historical Commission.
Paula Leonard served several years on Westport’s PTA Council, and for nearly 20 years was chairwoman of the Senior Services Commission, helping to plan and build the Westport Center for Senior Activities.
“I was saddened to hear about the passing of Dick Leonard,” said James Lomuscio, WestportNow associate editor. “He was the first person I interviewed for my first Westport story in the 1970s, my first impression of the town and a good one.
“Dick can best be described as a combination of educator, tough union guy and the qunitessential gentleman,” he added.
“A teacher through and through who put students first, he was always a fighter for his fellow teachers as head of the WEA, which operated out of the Kemper-Gunn House then on Church Lane.
“As union head, he held strong at a time of soaring interest rates, double-digit inflation and teachers’ contracts that had been locked in single-digit raises. Yet despite the uphill battles, he worked well with the school board, then Schools Superintendent Kenneth Brummell and the superintendents that followed.
“I last interviewed him a few years ago when I did a series on seniors who left town.”
Leonard is survived by his wife, five children, and 11 grandchildren.
A memorial service will be held Sunday, June 3 at 2 p.m. at Town Hall. (Time changed from 4 p.m.)
In lieu of flowers, donations can be made in his name to the Westport Library (20 Jesup Road, Westport, CT 06880, http://www.westportlibrary.org).
—James Lomuscio contributed reporting
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The family released the following obituary:
Richard Carey Leonard (Dick) passed away May 1st at the age of 88. He leaves behind his five children and his loving wife of 60+ years, Paula.
Dick Leonard had an outsized impact in his roles as English teacher at Staples High School, President of the Westport Education Association (WEA), attorney, and family man. He approached life as an adventure, even a competition—in the best sense of that word, “to strive together”—and inspired his five children through his example.
Born the youngest of four sons on December 10th, 1929 in Brooklyn to James and Charlotte, Dick attended St. John’s Prep and was in the first graduating class from Fairfield University. He served as a Navy pilot in the mid-1950’s and liked to claim that his posting in Bermuda to “do reconnaissance on Chinese submarines” was critical to the U.S. effort; he had great respect for those more directly engaged in the Korean conflict.
After a brief stint flying for TWA, Dick decided he preferred people to machines and became an English teacher. His first year at Staples High School was 1958. Dick spent over four decades teaching several generations of Westport teens how to write with purpose and clarity and to 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 twenty years, Dick led the effort to attract, retain, and adequately compensate the teachers who serve Westport’s children, making Westport’s school system one of the finest in the country. His skill as a negotiator on behalf of teachers was legendary.
Dick was a central figure in the 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, which would prove invaluable in his labor negotiations.
In retirement, ever the teacher, Dick began holding short story discussion seminars — with small groups in private homes, the Westport Public Library, the 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 and squash and finally tennis—his greatest love, and a sport he played vigorously into his late 70’s.
His poaching at the net on the doubles court frustrated many an opponent . . . and all of his children! Dick and Paula introduced Clan Leonard to Biddeford Pool, Maine, in the summer of 1974. In 1997, Dick and Paula built a second home there—“The Boathouse”—that continues to serve as a family gathering spot for summer fun.
Those who knew Dick well understand how important his vegetable garden was to his image of himself. Tomatoes were his specialty, even 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 five children, and his eleven grandchildren. Rick and Amy Leonard with Lizzie and Charlie; Jim and Story Leonard with Kelsey, Molly, and Campbell; Anne and Jim Hardy with Will and Ned; Carey and Cheryl Leonard with Amanda; and Colin and Kadie Leonard with Megan, Annie, and Sophie.
The family welcomes all who would like to remember Dick Leonard to join us for a memorial service on Sunday, June 3 at 2 p.m. at Westport Town Hall on Myrtle Avenue. (Time changed from 4 p.m.)
In lieu of flowers, the family asks that those so inclined make a donation in Dick’s name to The Westport Library, 20 Jesup Road or http://www.westportlibrary.org.
