1955-PresentNatalie Pinto Daley: Fearless Teacher in the Gloucester Public School SystemPeople and Communities, Government and Public Service, Education, 400 Stories Project

Hover over image to zoom

By Carla L. Grillo


The following story is an excerpt from the full profile on Natalie Pinto Daley appearing in The Past Is A Present, a book by local author Carla L. Grillo highlighting the life stories of 28 women and men from Gloucester’s diverse Senior community. Sponsored by the Friends of the Gloucester Council on Aging—and over five years in the making—The Past Is A Present features over 500 hours of oral histories tracing each Senior’s unique personal background. Curated with hundreds of historical photographic images and contemporary portraits by local award-winning photographer Bill Sumner, the book is available online at www.pastisapresent.org and at The Bookstore of Gloucester, Dogtown Books, and the gift shops at Cape Ann Museum and The Gloucester House. 100% of sale proceeds benefit the Gloucester Senior community.

Natalie Pinto Daley: Fearless Teacher in the Gloucester Public School System


Life truly does come full circle. Back in the late 1960s, before she became Mrs. Daley, “Miss Pinto” was my seventh- and eighth-grade English teacher at Central Grammar School. She would rigorously drill us in English grammar and composition, and I distinctly remember one of the exercises was to write an essay about my family’s history. Now, more than fifty years later, it is only fitting I have the privilege of writing a brief history of her remarkable life.

Natalie recalls being surrounded by books as a young girl, “I was constantly reading.” Huckleberry Finn was her favorite childhood book, and as a young adult, she had a particular fondness for Charles Dickens’ A Tale of Two Cities. “While we didn’t have a lot of money, my mother stressed educational activities—books, puzzles, art supplies, crayons and paper were always readily available. We could all read before entering the first grade. My father focused on the importance of getting an education and made very clear it was not optional.” She laughs as she remembers, “From a very early age, I always played ‘teacher’ with my siblings and friends”—an uncanny foreshadowing, as teaching was to become her life’s passion. She also directed many one-act plays with her neighborhood chums, another budding talent used in her future career as she was acclaimed for dramatically “acting out” scenes from the various plays or books on her required reading list.

After graduating from Gloucester High School in 1955 and Salem State College in 1960 (BA/ English and History), Natalie taught for two years in the North Bennington, Vermont School System, teaching English and developmental reading to grades 7–12. “I couldn’t afford a car back then, so I would either walk to classes or hitch a ride with other teachers.” However, the lack of a car became problematic, so she returned to Gloucester and spent the next two summers working as a waitress at the Marguery Restaurant in Ipswich, where “I earned enough tip money to buy my own car with cash.”

In 1962, Natalie was admitted to the Master’s Program in Indian Folklore at the University of Arizona, but discontinued her studies for health reasons. (Later, she received a Certificate of Advanced Graduate Studies in Reading and Special Needs from Gordon College in 1969).

At just 24 years old, she secured her first job teaching in the Gloucester Public School System in 1962, where she would dedicate the next 40 years of her life fearlessly teaching English to grateful, yet mildly terrorized Gloucester students: Central Grammar for the first 10 years (1962–1972), teaching grades 7 and 8; the Fuller School, 1972–1980; the O’Maley School, 1980–1983, where she was English Department Head and taught grades 7–12; and her final 19 years at Gloucester High School until her retirement in 2002.

When asked to name her favorite book or play to teach, Natalie smiles and says, “Neither, because it’s a poem, Beowulf.” (She is referring to the epic Old English poem anonymously written circa 700 AD). “It was my absolute favorite to teach, with Macbeth being a close second. Most teachers didn’t teach Beowulf because they couldn’t make it relatable to kids, but I could because I play-acted every book I taught (remember the one-act play directing as a young girl). I would read it out loud and really ham it up—sometimes I used to think the kids thought I was crazy!” But how did she make Beowulf and Macbeth relatable to modern-day teenagers? “Beowulf is a blow-hard; he can do anything better than everyone else. He was a superhero of the 8th century. Macbeth starts as an 11th-century Scottish superhero before his unbridled ambition leads to his destruction. I related both Beowulf and Macbeth to modern-day superhero comics of the 1980s, such as Spider-Man and Teenage Mutant Ninja Turtles— the students just loved it. They were completely shocked to find out how much I knew about comic books.”

Notice of her retirement received front-page coverage in the June 1, 2002, Gloucester Daily Times. Over 100 people—including past and present colleagues and students, along with family and friends—attended a surprise retirement party at Cameron’s to honor this “institution-al icon” of the Gloucester Public School System. She reminisced, “Many past students gave testimony to my being tough and pushing them to the limit. That’s very true. But I had high expectations for all the kids, and I never deviated from that standard.” In retirement, she continues to tutor special needs students on a volunteer basis.

Natalie has been a trustee of Cape Ann Savings Bank since 1989, when Henry Jones called to let her know she was being nominated for the position. She was the first woman trustee appointed to the Bank and is also Clerk of the Corporation. “Being a trustee of the Bank has been a tremendous experience for me,” she comments, “one I would never have had by exclusively being a teacher.”

It doesn’t seem that long ago sitting in her class at Central Grammar. “Miss Pinto” was a strict disciplinarian—her classrooms were entirely under her control. I don’t recall her ever having to raise her voice; she did it all with a steely glare that could freeze you in your seat. Yet, behind the tough exterior—she admits to having been borderline tyrannical, “but I think I mellowed with age”—was a committed teacher who genuinely cared about her students.

It’s not often one gets an opportunity to thank a revered schoolteacher publicly. “Miss Pinto,” on behalf of all your students over your illustrious 40-year teaching career in the Gloucester Public School System, thank you so much for making a difference in our lives.


Revered long-time Gloucester schoolteacher Natalie Pinto Daley turned 85 years young on October 27, 2022. The day after, she celebrated her “celebrity” status with the rest of “The Gloucester 28” at a joyful book launch party for The Past Is A Present held at The Gloucester House. Natalie could be seen gleefully handing out her signature to her “yearbook” profile for all who asked.


I am grateful to award-winning local photographer Bill Sumner who took the contemporary cover photograph of Natalie during a photo shoot on Stacy Boulevard in October 2020. Bill contributed his time and professional talent to create the beautiful portraits of the 28 Seniors profiled in The Past Is A Present. He passed away in December 2022 at 79 years old. I was honored to call him my friend.


The Friends of the Gloucester Council on Aging is a 501(c)(3) charitable organization incorporated in the Commonwealth of Massachusetts in 1988. We are currently celebrating our 34th anniversary in our mission of working collaboratively with the Gloucester Council on Aging and the Rose Baker Senior Center by providing financial assistance and technical expertise for programs and services benefiting the broader Gloucester Senior community. For more information about the Friends, including a sample of projects funded and supported by the Friends since its founding, please visit: www.friendsofthegcoa.org.


Carla L. Grillo is the creator, author, and editor of The Past Is A Present project—celebrating the incredible lives of 28 Seniors from Gloucester’s Senior community, affectionately referred to as “The Gloucester 28.” Over five years (2017–2022) in the making, more than 500 hours of oral histories were chronicled for The Past Is A Present.

67categories 1576total entries 400+years 845searches