Friday, July 19, 2024

Les Oliver on the cover of a quarterly journal called Growing Up in North Cambridge launched by Stephen Surette, a colleague of Oliver’s from Cambridge Rindge and Latin School. (Photo: Les Oliver)

The history of North Cambridge is integral to Leslie Oliver’s own story. He was born there in 1940 and has lived there his entire life. His days being a newspaper boy, attending and being a parishioner of St. John’s Catholic Church and as a student and teacher in Cambridge Public Schools had big effects on the person he became and what he has been able to accomplish, he says.

In 1952, he got a job at Davenport News delivering newspapers in the Rindge Field neighborhood for four years. From 1957-1965, he washed dishes in Harvard dining halls. After 38 years as a teacher and administrator in the Cambridge Public Schools he retired and became an adviser to Harvard graduate students, showing that anything is possible for a local boy from North Cambridge.

His early days were filled with joyous moments playing with friends. Whether it was roaming around Fresh Pond playing “cowboys and Indians,” pretending they were horses or swimming at Jerry’s Pit – North Cambridge’s own Cape Cod – there was plenty of fun to be had. Tag and baseball with a broomstick were common games on the street. As a teen, if you were cool, you joined the athletic club called The Naturals, essentially an intimidating gang of teenagers; Les still has his Naturals club black jacket. Being in the club meant you would hang out with the 20 or so club members, play pinball at the Hollywood Spa, sometimes making a little money off the machines, and drink sodas from the fountain.

Les’ mom worked hard to take care of him and his three brothers. The first house they lived in did not have a shower or a tub, so everyone had to shower at the Rindge Shelter. When his parents got divorced, his mother moved them into a Middlesex Block apartment over a bar on Massachusetts Avenue; she worked downstairs at Ted’s Tap. The teenage Les would go downstairs to the bookie joint and place bets and play pool, having no idea the notorious Winter Hill Gang was running the operation. Even so, it was a great place to live – he was right in the middle of the neighborhood.

Young Les. (Photo: Les Oliver)

When his mother remarried, his stepfather bought a house where he could have his own room. At 16, Les quit high school and wanted to start working – but after two jobs in Boston as a stock boy, he realized school might be the better option. With the help of a friend, Tom Danehy (later mayor of Cambridge), Les found a way back to school. Tom got the help of his father, who at the time was assistant superintendent of schools. He asked the principal to let Les back into school on probation. After school he would stop by the Cambridge YMCA, then work at Harvard, a job that continued when he graduated and attended Northeastern University. Commuting to college was made easy by his motor scooter – also very popular with the girls in Harvard Square.

Most kids of that era dated within their neighborhoods and found entertainment locally, such as going to the movies. Going out to eat in restaurants was not as common.

Les and Norm Oliver visiting Santa circa 1946, probably at Grant’s in Davis Square, Somerville. (Photo: Les Oliver)

While Les’ future wife went to Cambridge High and Latin School, they never met there, because she was two years behind him. One day he was waiting for the bus in Harvard Square when a girl he knew from high school introduced him to his future wife: Sandy Fiore of Appleton Street. Later, at 24 and about to graduate from Northeastern, he went to a local bar called the One-Two Club and found Sandy there again with a bunch of friends. Les walked up and asked her to dance. He got her phone number and they started dating – as easy as that. Two years later they were married.

When it came to other large life choices Les had to make, he found that going back to high school allowed him to write a new history for himself. After college Les taught in East Cambridge, then went on to get his master’s and a degreed in education at Boston University. , He wound up being part of the Cambridge school system from 1945-2003, first as a student, then as a teacher, learning firsthand that attitude and motivation are huge factors in how well kids do in school.

Backyard sports on Reed Street in Cambridge in 1948. (Photo: Les Oliver)

Les developed an interest in history and its connection to his hometown and found that Cambridge was the best place to grow up and live with a love of history. He is proud that the U.S. Army was founded on Cambridge Common when Washington took control of the local militia. Living in Cambridge allowed Les to see the Rev. Martin Luther King Jr. eating in the dining hall where he worked. John F. Kennedy walked by him during Harvard’s 1960 commencement.

During a Vietnam War demonstration in Harvard Square in 1969, he was almost hit on the head by a cop with a billy club; a friend from the dining hall pushed the cop away. In that era, when things were a little uncertain or chaotic, Northeastern and St. John’s Church kept him grounded.

The Middlesex block in the 1940s. Les lived above Celli’s. (Photo: Cambridge Historical Society)

All around him history was in the making and the “small town” was changing. His family had an ice box instead of a refrigerator when he was a kid, and had ice delivered; he remembers putting up a sign in the window when they needed more. Oil was brought up from the basement as needed for the oil stove. He can remember watching the 14 bars lining Massachusetts Avenue disappear slowly after World War II, and the first time he saw a television in Dudley’s Furniture, two blocks from Frank’s Steakhouse. Porter Square went through big changes; much of the area used to be fenced in, the estate of the Rand family, but after 131 years the land was sold to be developed into the Porter Square Shopping Center. The center opened in 1956.

Les Oliver and Sandy Fiore on their wedding day in 1966. (Photo: Les Oliver)

A lot of kids and families began moving to Arlington because they couldn’t afford a single-family home in Cambridge. In North Cambridge a single-family home was $25,000, and families could not afford the monthly payments. Newcomers and transients moved in and continue to come and go – but not Les.

Now, after retirement, he enjoys a bourbon old-fashioned and joins his friends every Saturday at a different restaurant in the area. A positive attitude and small-town connections can change your life. Seen through the life of Les Oliver, North Cambridge is truly what you make of it.


About History Cambridge

History Cambridge started in 1905 as the Cambridge Historical Society. Today we have a new name and a new mission. We engage with our city to explore how the past influences the present to shape a better future. We recognize that every person in our city knows something about Cambridge’s history, and their knowledge matters. We listen to our community and we live by the ideal that history belongs to everyone. Throughout 2023, we are focusing on the history of Cambridgeport. Make history with us at

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Emily Harris is a volunteer for History Cambridge and a resident of North Cambridge.