Remembering Mike Silverstein, Alan Chalk

Two veteran Westport educators died recently. Mike Silverstein and Alan Chalk worked at Staples High School during dynamic, fervid years. Their marks on their students — and the school — were strong.


Melvin (Mike) Saul Silverstein of Worcester, Massachusetts, died on May 18. He was 95.

An award-winning educator, prized friend and co-worker, he took on diverse roles in education and his communities and was a longtime advocate for the less fortunate.

Silverstein grew up in Hartford, the youngest son of immigrant parents from eastern Europe. He attended Hartford public schools and worked with his siblings at the family-operated People’s Dairy, a milk processing and delivery company.

Only 17, he enlisted in the US Army Air Force in 1943, training to serve as a gunner on a B-24 Liberator just as World War II ended. He was awarded the WW II Victory Medal, American Campaign Medal and Good Conduct Medal.

After his discharge in May 1946. Silverstein attended Hillyer College (now the University of Hartford), where he met his wife Florence. They married in 1948. He graduated in 1950, and obtained his Masters of Education in 1956.

He became a teacher and counselor for Glastonbury High School, then in 1960 moved from East Hartford to Norwalk, and joined the guidance staff of Darien High School.

During the summer of 1966 Silverstein led a group of 22 students to Israel on a service project under the auspices of the New York City-based 92nd Street Y.

In 1967 he took on a guidance role at Staples High, and dramatically expanded it. Over 2 decades he became a fixture in Westport education — active and pioneering in career counseling, adult education and work/study programs.

In 1978 he was named the outstanding counselor in the state of Connecticut by the Connecticut School Counselor Assn.

He also volunteered at the Hope Center in Bridgeport. Simultaneously he was an energetic member of Temple Shalom in Norwalk, becoming principal of the religious school.

Melvin (Mike) Silverstein

Silverstein was married to the late Florence Heath Silverstein for 68 years. He is survived by his children: Lucy Tannen of Framingham, Massachusetts; Jeffrey Silverstein of Blackstone, Massachusetts; Timothy Silverstein (Sally) of Norwalk, Melanie Rosenbaum (Bruce) of Thorndike, Massachusetts.

He also leaves grandchildren: Caroline Savitzky, Alex Savitzky, Kate Silverstein, Ben Silverstein, Lindsay Navarro, Michael Silverstein, Joseph Rosenbaum, and and, as well as great-grandchildren; Devin Smith; Paige, Jordan and Zoey Savitzky; Jonathan and Nicole Navarro, and Madilyn and Salma Delgado-Savitzky.

Silverstein is also survived by his brother Nathan Silverstein of Branford, Connecticut; cousin Marilyn Benson of Bloomfield, Connecticut, and many nieces and nephews.

He was predeceased by his brother Irving and his twin sister Evelyn Fain.

A memorial service will be held late in June in Hartford, followed by a social gathering to share memories and thoughts. Those wishing to attend should call Jeff Silverstein: 774-270-0769.

In lieu of flowers please consider donations to the Alzheimer’s Association, Diabetes Research Institute, University of Hartford, or the Jewish Healthcare Center in Worcester, MA. Click here to leave online condolences.


Alan Chalk died at home, surrounded by love, on May 31. He was 89.

Chalk was born in 1931 in Springfield, Massachusetts. He and his beloved wife Norma LaFlamme married 70 years ago.

Chalk joined the Navy during the Korean War, and did 2 world tours. In 1952, his experiences traveling in Japan and meeting the people touched him deeply. A lifelong journey commenced.

He received his teaching degree at Wesleyan University, and attended the University of Iowa Ph.D. program. He moved to Fairfield in 1961, where he lived the rest of his life.

His first teaching position was at Staples High School, developing an innovative creative writing program. He became chairman of the English Department at Weston High School in 1972. He was voted Teacher of the Year in 1989. He retired from Weston High School in 1991.

Alan Chalk

Chalk began a new career as consultant, writer and teacher specializing in postwar and contemporary Japanese literature and film, and developed an extensive library. He created the curriculum for the first Center for Japanese Study Abroad magnet school in Norwalk.

He traveled extensively but Japan remained closest to his heart. He led tours for students, teachers and family, sharing his knowledge and love of Japan. He wrote novels, short stories and poetry, many inspired by his travels in Japan.

Chalk was a master teacher, writer, wood sculptor and photographer. He also found time to raise 5 children with Norma, remodeling the house, and creating beautiful gardens.

Chalk said, “I exist in a style of anonymity and I ask a thousand questions. I find that I ask questions I don’t have the answer to and this may be the key to effective teaching. I am always learning. Every day.”

He loved teaching. His deep care for his students and staff is reflected in the letters from students and parents, thanking him for his inspiration and caring during pivotal times in their lives, as well as those from teachers whom he helped to become master teachers themselves. He impacted many lives.

A plaque on his wall — a gift — reads:”A teacher affects eternity; he can never tell where his influence stops.”

Chalk is survived by daughters Lynn and Karen; sons Brian, Gary and David; son-in-law Scott, daughter-in-law Laura; grandchildren Jesse, Danielle, Gabrielle, Billy, Maya, Sammy, Nicole and her family Jeff, Tenley, Caiden Blaiotta, and great-grandchildren Lyla and Jude.

He was predeceased by his wife Norma, an integral part of his accomplishments and to whom he gives much of the credit.

Dan Magida, a former student at Staples over 50 years ago, was one of his best friends.

Contributions in his memory can be made to Habitat for Humanity of Coast Fairfield County, where his wife was a longtime volunteer.

6 responses to “Remembering Mike Silverstein, Alan Chalk

  1. Clark Thiemann

    While both of these fine teachers retired before I made my way through Staples, I am consistently impressed by the quality of teacher Westport has and continues to attract. All the best to their families on lives well led.

  2. Wendy Crowther

    I was one of the fortunate students to have taken a class with Mr. Chalk. It was one of the most memorable classes of my schooling life. Here’s one reason why: I was new to Staples and was a shy student who sat in the back. We were given an assignment to write a very short story using the style of one of the authors we’d studied. I chose Hemingway. A few days later, Mr. Chalk read one of the better submissions aloud to the class. It was about a WWII soldier who was crouched in the trenches awaiting orders to run into battle.

    Mr. Chalk didn’t reveal who’d written the story but asked the class if they thought it had been written by a boy or a girl. The class guessed “boy.” He said, “Nope, it was a girl.”

    That girl was me.

    I’ve never forgotten that incredible compliment nor the creativity he inspired in me and in so many others.

    • Fred Cantor

      Wow, I remember having that same exercise of writing a story in the style of one of the authors we had studied. It was terrific. Mr. Chalk taught AP English senior year and, if my memory is correct, he also served as the faculty advisor for the literary magazine; he was a very nice guy.

  3. Lee Fleming

    Mike Silverstein was my sister’s father-in-law and I got to meet him (and Florence!) in the mid-1980s. He always made me feel like a member of the Silverstein clan and I am happy I have many good memories of them both, especially all of the holidays we shared over the last 35 or so years.

  4. Christine Bisceglie

    How sad, but a day I knew was coming.

    Respectfully , When I look at this photo of Mr. Chalk’s I feel as though I am looking into the face of G_D. How fortunate to be one of his students at Weston High School. Mr. Chalk graced all of his students with sincere devotion and respect. For me he has never been forgotten nor ever will be. Thank you Dan for featuring Alan Chalk as an extraordinary teacher. He is already missed immensely.

    To the Family – May you be comforted in this time of grief by the many who feel the same as I do about your special father who we fondly knew as ” Mr. Chalk. ” He taught literature by breathing life into the classics resulting in a student receiving oxygen which was capable of taking them to greater heights. Mr. Chalk’s goal.

    It was fortuitous for mr that our paths crossed again at Brien McMahon High School ; year the Center for Global Studies was started. Mr. Chalk loved to introduce students to the Japanese Culture. Hearing Mr. Chalk speak about Japan was nothing short of mesmerizing. In fact when he spoke his students leaned in to listen. In all the time I knew him , he never raised his voiced. Never.

    I still have books that he so generously gave to me so I too could feel the same magic that he did in discovering great writing. Alan Chalk wanted YOU you to be a reader and writer. His passion was contagious. May he now be at peace. I trust he has been reunited with his wife Norma who he always spoke fondly of.

  5. Robert M. Gerrity

    I’ve told more than a few people about Alan Chalk and my AP paper on Nikos Kazantzakis (Zorba the Greek and much much more.) Alan and I went back and forth on theme–I could not persuade him and he could not un-persuade me. We were not in good temper at the end–a mutual agreement to acknowledge that we didn’t understand each other (and oh! the grade!), but that didn’t impact what followed: a positive teacher-student relationship over editing/producing Soundings 1966, him writing me a wonderful letter of recommendation for college, and inviting to his house for an end of year party. I also tell people about his submarine novel that he’d go on about for a bit in the class.

    I am so happy to see he followed all of his passions to the very end and so creatively over the decades. Must World Cat for his published work now. And I was just thinking about making another go at Kazantzakis’ The Odyssey, A Modern Sequel this summer; a vast epic poem about how Odysseus just can’t stay home. Bought it at Klein’s in 1963, have read huge chunks but technically not finished. Whenever I’ve picked it up or boxed it and unboxed it, a memory of Allan has always been close to mind.

    And as with Christine, and likely countless other acolytes, at that family party, he gave us books as gifts. Mine was another poet, the American Theodore Roethke, warmly inscribed by Alan on the front paste-down page. I’d written papers on two of the poems:
    THE WAKING [last two stanzas]
    Great Nature has another thing to do
    To you and me; so take the lively air,
    And, lovely, learn by going where to go.

    This shaking keeps me steady. I should know.
    What falls away is always. And is near.
    I wake to sleep, and take my waking slow.
    I learn by going where I have to go.


    ONCE MORE, THE ROUND [complete]:
    What’s greater, Pebble or Pond?
    What can be known? The Unknown.
    My true self runs toward a Hill
    More! O More! visible.

    Now I adore my life
    With the Bird, the abiding Leaf,
    With the Fish, the questing Snail,
    And the Eye altering All;
    And I dance with William Blake
    For love, for Love’s sake;

    And everything comes to One,
    As we dance on, dance on, dance on.

    And: Kazantzakis’ Odysseus points his fair ship northwest for the last voyage:
    “The seven-souled man stood up, hailed his troop ….
    Forward, my lads, sail on, for Life’s breeze blows in a fair wind.”