(Editor’s note: This piece accompanied by more photos originally appeared in Gloucester400.)

A signature moment in the business world is an interaction that goes from ordinary or forgettable to an experience that people remember. I believe moments like these, especially while growing up, can also happen in our personal lives. They shape who we are, how we make decisions, and how we conduct ourselves. One of my most impactful signature moments happened at my paternal grandfather Caesar’s small grocery store on Friend Street in Gloucester, Massachusetts. It was the early 1980s, but the memory is so vivid and colorful, it feels like it was yesterday.

It was a perfect summer day in the hard-working Portuguese neighborhood affectionately known to my family and locals as Portagee Hill. I was helping out at my grandfather Caesar’s store by doing odds and ends and mowing his postage-stamp-sized backyard. Middleton Playground across the street was its usual beehive of activity, with kids playing on swings and dodging water balloons. The playground was the kids’ domain during the day, but nights were reserved for the Adult Basketball League that drew dozens of spectators and, borrowing from Yogi Berra, “kept the parents off the streets.” Because of the narrow entrance and tight quarters, more than one car would leave at night with a scratch or two over the years.

The early ’80s were good to Gloucester and a great time to be a kid. Fishing boats crawled home from Georges Bank with full holds; the waterfront was bustling thanks to a healthy market-ready fish population; and something called cable TV was starting to make its way into homes, street by street. The recently arrived Moonies provided more than enough scuttlebutt at local bars. Saturdays were reserved for errands where adults arrived early at local stores like Empire, banks, and supermarkets to avoid long lines while the kids made their way down to Main Street Arcade with pockets full of quarters.

While Roland’s Market itself was small and unremarkable, it was still packed with enough necessities, cigarettes, and prepared foods, which saved locals who didn’t own a car from spending money on a taxi ride to a grocery store. When you entered Roland’s, you were welcomed with warm greetings in Portuguese, a bone-rattling handshake from Anibal Simões (a good friend of Caesar’s), and the sound of waltz music from a fuzzy AM radio. To the kids’ delight, the shelves were lined with candy, the latest trading cards, and sour pickles. What the store lacked in square footage and wide aisles was more than compensated for with the wide selection of items including Caesar’s famous linguiça, and his legendary customer service.

Reminiscing brings me back to my signature moment in the store, thanks to a memorable customer that walked in. If it weren’t for her attire, I might have forgotten about the whole incident. She was a Portuguese widow clad in black from head to toe, despite the sweltering heat. Because I had never seen anyone like that before, I was spellbound. She was of medium height and very frail, with a weathered and sunken face that made her nose appear bigger than it actually was. She kept her silver hair in a tight bun making it easy to see her small, piercing brown eyes. She was probably in her early 70s, but to my 11-year-old eyes, she looked about 100. I wondered if she knew the peculiar neighbor of similar age who I saw earlier that day cutting her lawn one blade at a time on her hands and knees with clippers.

She only had one thing on her shopping list that day. Cigarettes. Without saying a word, Caesar produced two new packs wrapped in shiny foil and handed them over. No money was exchanged; if she spoke, it was barely above a whisper. She signed a small piece of paper and was out the door as fast as she came in. If you didn’t have enough money for your purchase, Caesar would take what you could afford or have you sign an IOU slip that would go into an old-fashioned turnstile caddy.

After she left, I checked the caddy to see how much she owed, knowing each pack cost around $1.27. I couldn’t find the IOU slip in the caddy but did notice it crumpled up in the trash. Caesar had thrown it away. After more digging, I noticed many of the slips were several years old, and some were too faded to read. Something told me this wasn’t the first promissory that he had thrown away. Charity to those in need at Caesar’s store was more important than profit—a signature lesson that has stayed with me to this day.

Commitment to the community

To call Portagee Hill a tight-knit community back then would be a major understatement. The store fittingly sat on the highest point of Friend Street and was just as much a community center as it was a place of business. If the store was the flagship, then Caesar was the ballast that kept the neighborhood afloat. It’s no wonder why many people referred to him as “King of the Hill.” Whether one needed advice, a loan, coaching, or someone to talk to, they could get it at Caesar’s. Barry Sousa, who lost his father at an early age, looked to Caesar as a mentor, and I’ve been told more than once that Caesar helped kids get on the “straight and narrow.” Caesar, who kept fistfuls of cash in a shoe box (like many who lived through the Depression), made sure that if a kid needed a glove to play Little League or a bike to ride on, they would get it.

Caesar’s soft heart, loyalty, and sense of community contributed to his success—not just as a grocer but as a well-respected man in the Portuguese community. He never forgot where he came from and the opportunities he received in America. Besides teaching kids how to throw a baseball or make a basket, he helped new immigrants secure jobs at Gorton’s of Gloucester and advocated for poor and voiceless widows and their children. He interpreted documents for those who did not speak English and placed phone calls on their behalf when asked. Caesar was known for his sound advice and generosity and is fondly remembered today by many, even though he passed away in 1992.

If you needed something, “go to Caesar.” If the hoops needed a net, “go to Caesar;” if a kid needed a bike, “go to Caesar.” He was much more than a store owner; he was a personal coach, mentor, and most importantly, everybody’s friend, especially to the kids.

When I return to Gloucester, I often run into people like Barry Sousa, Don and Joyce Lacerda, Tom Clarke, Elsa Ascenso, and Ellie Bertolino (Bolcome), and it’s rare when my grandfather’s name does not come up in conversation.

Caesar, who worked 6½ days a week, every week of the year, didn’t have time to go for things like haircuts. So, haircuts had to come to him. Just ask Joe Lucido. And judging by Caesar’s legendary driving skills, or lack thereof, that was a good thing. When he ventured out, it was usually to a family picnic or to treat us to a hearty Sunday night supper at Captain’s Courageous on Rogers Street or the only remaining restaurant he would recognize today, The Village in Essex. I was always on my best behavior because nights out with him were rare, and I wanted that dollar that he promised me for every hamburger I ate since I needed to bulk up.

Caesar’s early days

It is hard to imagine that Caesar’s life in America almost did not happen. His mother left the fishing village of Fuzeta in Portugal in 1915 during WWI with 3-year-old Caesar and his three older siblings to join his father who was already in Gloucester.

Their ship, the S.S. Roma, was stopped and boarded by a German U-boat midway across the Atlantic. Europe was ablaze in a quagmire of trench warfare, but luckily, unrestricted submarine warfare had yet to be declared, and the ship was spared from a torpedo. Instead of sinking them, the German captain requisitioned as much food and supplies as he could in return for allowing the Roma to continue on its journey. Now, the huddled masses seeking a new life were hungry, huddled masses.

Luckily, Caesar’s resourceful and resolute mother had hidden a meager amount of food in her long skirt that had to sustain them for the rest of the passage to Providence, Rhode Island. Being the joker that he was, I remember Caesar telling the story to customers more than once that the U-boat commander told his mother that he (Caesar) was the ugliest baby that he (the commander) had ever seen, but if she named him Caesar, he would spare the ship. I believed him for the longest time. And speaking of jokes, Caesar got a kick out of challenging kids to say the word “Czechoslovakia” in return for free candy. And as legend goes, when I was first introduced to him at the store as a two or three-day-old baby, he tried to hide me after seeing my blonde locks and blue eyes. I was the only blond-haired, blue-eyed kid in my neighborhood!

My grandfather’s original Portuguese name was Sezinando Rolão, but he became known in America as Caesar Roland. Like many immigrants from Europe at the time, they had to accept a new surname upon arriving in order to be “Americanized.”

As a teenager, Caesar would put his 6’1” height and athleticism to good use on the basketball court back when games were played at City Hall. Later, he co-captained the Essex Agricultural School team (Essex Aggies) and continued to play with the Gloucester Athletic Association semi-pro team.

With his strong work ethic forged during his youth, Caesar worked as a playground supervisor during the Works Progress Administration (WPA) days and put a fresh coat of paint on the iconic “Hesse House,” also called “The Sherman Cottage,” at Good Harbor Beach. And never one to shy away from the sea, he followed his father’s footsteps to the Grand Banks on various Portuguese fishing boats.

Caesar continued to fish for more than ten years until his store-owning father-in-law, James Silva, retired due to poor health. Caesar then purchased the Market on “Portagee Hill,” the apartment above, and the small house in the back. Caesar ran the store at the start with his brother-in-law, Benny Silva, behind the butcher’s block. Caesar, his wife Alice (Silva), and their first-born son, Kenneth, moved from the Roland homestead at 67 Friend Street to 52 Friend Street in the late 1940s. A second son, Robert, was born in 1947, and a daughter Elizabeth arrived in 1952.

Leadership on and off the court

Although the store kept him busy, Caesar’s passion for sports would lead him to found and curate one of the best adult summer basketball and street hockey leagues on the North Shore. The league showcased Gloucester’s best hoopsters and attracted quality players from out of town, including local small college talent. On those hot and humid nights, players ran to Caesar’s store to cool off in his oversized ice locker! In 2002, Caesar was posthumously named to the Gloucester High School Athletics Hall of Fame for meritorious service.

The Sawyer Playground (renamed Middleton Playground in 1976) on Friend Street was Caesar’s front yard. He flew the American flag daily, ensured the grass was cut and that litter including broken “Twin Lights” soda bottles were removed. The swings had to be in working order, and the basketball court ready for organized games. Caesar also created a lot of fond memories by organizing evening dances on the basketball court. He seemed to have an endless supply of badminton sets, basketballs, and baseballs to keep everyone busy and entertained. He was a life-long member of the Gloucester Fraternity Club and was proud to serve as Imperator during the 1950 Crowning Ceremony. Despite living through two World Wars, a pandemic, and the Great Depression, Caesar kept a positive disposition and personified the word “gravitas.” I only remember one thing that bothered him, and it happened every Thanksgiving in front of the TV, providing me with a lifetime of memories—past, present, and future: “Why does Detroit always get to play on Thanksgiving?” I agree.

My grandfather’s legacy

Even in the Caribbean, there are stories about Caesar. Not too long ago, I was vacationing in Aruba and ran into several natives at my hotel who were easy to spot with their Cape Pond Ice T-shirts. I was introduced to folks I didn’t know. When they heard “Roland,” they offered up a chair, poured some drinks, and stories about my grandfather’s generosity began filling my sunburned ears. For the next hour, it was like I was back on Friend Street, sliding on the scalding hot metal slide, trying to act cool around the “big kids,” and remembering my grandfather’s favorite advice as I swept the sidewalk: “Always push with a push broom.” That was his way of saying work smarter, not harder.

Today it is heartwarming to me that more than 25 years after Caesar’s death, a social media tribute page in his honor is thriving and active. The page not only honors Caesar, but a way of life and a community spirit. Posts include:

“I lived at 56 Friend (Street) next to Caesar for five years. Caesar gave me a bike when I moved there at nine years old.”

“Best of times.”

“Caesar was the best! Loved his jokes.”

“Mountain of a Man!”

“We would go over to Caesar’s all the time – what a great guy… he would make (you) feel at home… I was honored to bring my son to meet Caesar to get penny candy in his store… he was awesome.”

“Caesar was like a 2nd father to us, the best man ever.”

Today, the store is a residential house, and the playground is primarily a parking lot and a shadow of its former glory. But, now and then, I am reminded of my grandfather’s legacy and what he meant to Gloucester’s Portuguese community, athletes, and local kids when I think of the monument at the park where Caesar dedicated so much of his time. Its inscription came from a plaque given to him decades ago by thoughtful kids like Jose DaSilva, who pooled their money and took it upon themselves to show gratitude to the man that meant so much to them.

“To Caesar… the best friend a kid ever had…”