A tale of two Mastrangelos

By Michelle Boon

Posted on February 23, 2022

Photo: Courtesy of the Mastrangelo family

Up until the COVID-19 pandemic, Rocco Mastrangelo Sr. would come into Café Diplomatico every day for lunch.

The founder of the Little Italy café opened the doors in 1968, and it’s since become a favourite spot in Toronto. Known for its sunny patio, it’s the perfect place for pasta or pizza, but Mastrangelo Sr. always brought a meal prepared by his wife to eat at the café. If anything, he would order a coffee a la Rocco—a shot of espresso served in a cappuccino cup.

“God forbid if the coffee wasn’t good,” his son, Rocco Mastrangelo Jr. said in an interview with The Newcomer.

Even well into his 80s, the founder would get up from his seat to teach the barista how to make a proper Italian espresso. It was this dedication to Italian culture and attention to detail that fueled Mastrangelo Sr.’s long career as a business man.

Mastrangelo Sr. died in April 2021. He is remembered as the patriarch of his family, a masterful business owner, champion of Italian culture, community leader, and a patron of the arts. Before his successes in Canada, Mastrangelo Sr. started as an immigrant.

Journey to Canada

Rocco Mastrangelo Sr. was born in Anzano di Puglia, Italy in 1933. He was a sergeant in the military and a true Italian patriot. The only thing that could separate him from his homeland was family. His parents and a few of his siblings had moved to Canada and needed support. Reluctantly, Mastrangelo joined them in 1958.

“My dad fought for Italian culture until the last breath,” Mastrangelo Jr. said.

Mastrangelo Sr. started by importing Italian goods for his first Canadian job at a gift shop. Eventually he started opening businesses of his own. These included a gift store, and Bar Diplomatico, which would eventually become the beloved Café Diplomatico.

At the time, there was nowhere for Italians to socialize the way they would back home. In fact, authorities discouraged Italians gathering in the 60s and 70s. The café was one of the first in the neighbourhood to add an outdoor patio. It was the perfect place for people to enjoy espresso, gelato, and the company of other Italians.

Patron of the arts

The café is one of Mastrangelo Sr.’s most famous successes, but according to his son, Mastrangelo Sr. took great pride in elevating Italian arts in North America.

Italian concerts were generally held at casinos at the time, but Mastrangelo Sr. refused, saying “that’s not culture.” Instead, he promoted acts at venues like Roy Thomson Hall in Toronto and Place des Arts in Montreal.

He also opened several movie theatres, including Cinema St. Clair, where he would screen Italian films. One of the business owner’s favourites was Zappatore. In this 1980 film, Italian immigrant, Mario, feels torn between his success as a New York City lawyer and his humble upbringing in Italy.

This familiar story deeply resonated with Italian immigrants in Toronto. It is no wonder that there were lineups to see it at Cinema St. Clair.

Mastrangelo grew his archive of Italian films and rented them out to other theatres across North America. Although Mastrangelo Sr. has passed away, he continues to share Italian film with students at the University of Toronto where his film collection was donated.

A family business

Mastrangelo Sr. also shared his love of Italian culture and business with his children. His son, Mastrangelo Jr., recounted being instilled with a knack for business at a young age, spending most of his childhood weekends working with his family. Mastrangelo Jr. did a bit of everything: Making gelato at the café, working at the cinema with his father, and helping his mother at the family gift store.

In part, Mastrangelo Jr. credits these early years for his later successes.

“Not only did it teach me a lot about business and responsibility, it actually gave me a foundation of the strength, and the guts, to stick out my head to do other projects.”

Photo: Courtesy of the Mastrangelo family

In 1995, at the age of 24, Mastrangelo Jr. penned a deal on the back of a napkin to become part owner of the café with his uncle and cousin. He used his lifetime of experience working with his father to continue his legacy, while taking the café to new levels. Mastrangelo Sr. founded the café as a place for Italians. His son sought to capture the multicultural community of Toronto…with soccer.

All nations unite at Café Dip

Beginning in 2006, the owner started promoting the café as a hub for all soccer fans to watch the FIFA World Cup. Not just Italians, hence their slogan “Where all nations unite.” The first run of the event was such a success, it was recognized by the world soccer organization itself.

“I got a cease and desist order from FIFA, from Switzerland,” Mastrangelo Jr. said. “My uncle was like ‘You ruined us,’ and I’m saying ‘This is a good thing for us.’ A little place on College and Clinton is being acknowledged by the world federation of soccer. This is crazy!”

Photo: Courtesy of the Mastrangelo family

After a minor setback with copyright infringement, Mastrangelo Jr. rebranded the event and it continued to grow. In 2012, he took over his old elementary school and welcomed 1300 soccer fans to watch the Euro Cup. The event organizer is currently preparing for the FIFA World Cup, which will take place in winter of 2022. To combat the Canadian winter, Mastrangelo Jr. added a new, fully-enclosed patio, so fans can stay cozy while they cheer for their team.

First and second generation success

Rocco Mastrangelo Sr. was not initially a fan of the cold, culture, or the coffee in Canada. There were some aspects of the culture he never grew to like, but it didn’t matter. He brought the Italian culture he knew and loved with him and created a community around it.

He was a success in business and promoting art, but there is one accomplishment that rose above the rest.

“His biggest accomplishment would have been his wife, my mother, ”Mastrangelo Jr. said. “She worked and kept the family united […] she was the backbone. She worked every day in the gift store and that was their foundation; that’s what kept their engine running.”

Mastrangelo Sr. and his wife, Virginia, created a successful life together. Their children, including Mastrangelo Jr., continue this legacy. In 1968, Mastrangelo Sr. opened the doors of what would become Café Diplomatico. Over 50 years of renting later, his son purchased the property. In some ways, the current café owner has followed in his father’s footsteps. In many other ways, he has forged his own path with the work ethic and business savvy he learned as a kid.

The café has changed over the years, but it remains a place for Torontonians of all backgrounds to gather. As Mastrangelo Jr. put it, “That’s the great thing about the Dip, it’s unpretentious, very comfortable.”

You can keep up with Café Diplomatico on their website, cafediplomatico.ca, or visit them for pasta, pizza, or a coffee a la Rocco.

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