Winnipeg Jewish Review  
Site Search:
Home  |  Archives  |  Contact Us
Features Local Israel Next Generation Arts/Op-Eds Editorial/Letters Links Obituary/In Memoriam

Harry Kaplan: The King of Winnipeg's North End

By Myles Shane, posted here July 25, 2023

During my teenage years, I formed a lasting friendship with a guy named Shawn Kaplan, who remains one of my closest buddies even as I approach the age of 50. The Kaplans lived on Embassy, just a block away from my house on Tanoak Park Drive. Beyond our shared Jewish heritage, Shawn and I had many common interests, such as sports, girls, and a shared belief in making the impossible possible. But this story isn't about our mischievous adventures growing up. It's about his father, Harry.

Upon first meeting Harry, he came across as a larger-than-life figure, yet simultaneously stern, rigid, and no-nonsense. I remember a particular Shabbat dinner at the Kaplan's house when Shawn, against Harry's repeated requests, refused to take off his baseball cap at the table.

Eventually, Shawn was asked to leave the dinner table. Over the years, as I spent more time at their house, I gradually witnessed the emergence of Harry's light-hearted, funny, charismatic, and impulsive side. He has always been kind to me, but it was through writing this article that I began to understand the reasons behind Harry's demeanor.

One of my earliest and most vivid memories of Harry was when Shawn badly injured his back while playing basketball, resulting in the arrival of paramedics. As the paramedics rushed into the house carrying a gurney, Harry took a towel to their muddy shoes and screamed at them, "Take of your shoes before you come in. This is a house." This incident left a lasting impression on me.

Recently, I underwent a medical procedure to have polyps biopsied in my bladder. The doctor initially suspected cancer, and I immediately called Shawn to share the news. He managed to make me laugh and feel a little better in that difficult moment. We reminisced about the good old days, and for a brief period, I didn't feel as though life had cheated me out of its remaining chapters. A week later, Harry reached out to express his concern. By that time, I had learned that the doctor's initial diagnosis was incorrect, and Harry seemed genuinely relieved to hear that I was okay. Harry not only proved to be a great father but also an amazing friend.


Harry Kaplan's life story is deeply intertwined with his Jewish heritage and the experiences of his family during World War II. His family resided in Rovno, Poland, where Jews lived with uncertainty, fear, and the rising tide of anti-Semitism. Rovno, a vibrant city with a significant Jewish population, saw Jews playing a vital role in its cultural, economic, and social fabric.

Harry's parents, fortunate enough to leave the country before the war erupted, narrowly escaped tragedy when their home was targeted by the Nazis, who smashed a log through one of their windows, nearly killing their youngest son. Leaving behind their possessions and wealth, the family immigrated to Canada in 1939, settling in Winnipeg with meager funds after the Polish government seized their assets.

The hardships and challenges Harry's family faced leaving Poland and their subsequent settlement in Winnipeg shaped his appreciation for resilience and determination. He witnessed first hand how his parents built a new life in a new country, and this experience instilled in him a deep sense of gratitude and determination.


Initially, Harry's family lived in a farmhouse between Stonewall and Stony Mountain, where they had to learn farming skills to survive. Only 1,500 Jews had been allowed to leave and fortunately their family was picked. The farm area where they resided was also home to ten other Jewish families, and Harry's house served as a synagogue for the High Holidays.

Harry's parents were adamant for him to have a Bar Mitzvah. In order to accomplish this he had to move into the Jewish orphanage on Matheson Street where he was taught his Bar Mitzvah. At that time other kids who were truly orphans were also living at the orphanage. During this time Harry attended Luxton Elementary school.

Harry’s parents eventually moved to Winnipeg after the war and opened a small general store at 235 Dufferin Avenue. Harry can still envision the store as if it were yesterday, “My mother was a smart business woman. I remember they sold linoleum, materials, pots and pans.” Winnipeg in the 1930s was a bustling city with a strong sense of community. The north end, a working-class neighborhood, was known for its diversity and close-knit atmosphere. The neighborhood was characterized by row houses and small shops while families often lived in close quarters with extended family members or boarders. Harry vividly recollects the various homes he lived in, “We lived on Flora. We rented there for a month, then bought a house in Manitoba. In 1961 my parents built a house on Mathesison. I had graduated from pharmacy at that point and helped pay for it.”

Harry attended St. Joseph’s for high school. “We belonged to the YMHA on Albert Street. After workouts we’d have a scoop of ice cream with the girls at Dairy Dell. On Friday nights everyone would show up at the College Theatre. That’s where you were seen.”


Directly out of school Harry started working at Economy Drugs owned by David Stern. “In Winnipeg you needed to apprentice for two years before you went to university. So there I was Mr. Big Shot in high school working menial jobs behind the fountain serving customers sandwiches.” While working as a soda jerk at Economy Dave became in many ways a mentor or almost like a second father to Harry. Dave was always helping Harry, providing him advice and in my ways took care of him. Dave saw him as a bright young man, a hard worker but more importantly someone who had business savvy and had great charisma.

After completing his apprenticeship Harry attended the University of Manitoba and completed a degree in Pharmacy. After graduation Harry and a fellow classmate were looking to buy a drug store when the deal went south. Subsequently Harry’s mentor Dave Stern heard Harry was looking to buy a drugstore and offered him to become a partner in 1963, just as the store began its transformation into Economy Discount Drug Store. Harry and Dave became not only partners but best of friends, “Dave saw that I was young and had the makings that he liked. Honestly though I still to this day don’t know why he picked me. After I became a partner we’d be at the store by eight a.m and come home at one a.m everyday.


Harry's future wife, Barbara, had a serendipitous connection to him through their families' neighboring stores. Despite Barbara's family, moving away to Vancouver, fate brought them together again when Barbara visited Winnipeg in the summer of 1969. Harry happened to be at Sun and Swim on Pembina that day due to a broken air conditioner at his store. Introduced by Barbara's friend, Harry was initially hesitant but eventually impressed by the vision of loveliness standing before him. They dated for only three months but have been deeply in love for the past 53 years, showcasing how chance encounters and connections can shape our lives. The fact that their families already had a connection through their neighboring stores adds an extra layer of love to their magical story.

As an adult, Harry became a highly successful businessman, being a part-owner of Economy Drugs on Redwood and Maine. In 1973, Shoppers Drug Mart negotiated a deal with Harry and David to continue running the business, but it would become part of the Shoppers empire. Harry's son, Shawn, an accomplished chef who has prepared meals for Obama and other well known politicians, acknowledges his father's innovative and community-oriented approach to running the store. Harry organized events for seniors, invited celebrities and famous hockey players, and even arranged for Filipino dancers to perform in the store's parking lot during summer barbecues. He built a strong reputation for his dedication to the community, both as a respected businessman and as a valued member of the Jewish community in the north end.

Harry's impact on the north end is fondly remembered by his daughter, Carrie, an artist living and working in Los Angeles. She recalls his efforts to organize events, welcome notable visitors, and create a vibrant atmosphere at the drugstore. The store served as a gathering place for the local community, and Harry even hosted special events for doctors, offering them discounted shopping opportunities. His commitment to his customers and the community left a lasting impression.

At 92 years young. Harry Kaplan's life story exemplifies the strength of the human spirit, the power of community, and the resilience of individuals who have triumphed over adversity.

After writing and researching this profile I’m beginning to understand Harry. It would seem that Harry not only belongs to the north end of Winnipeg, but the north end has become an integral part of who Harry is. His upbringing in the north end instilled values of hard work, dedication, and the pursuit of education as a means to create a better life for himself, his parents, and his children after the Nazis took everything away from his family in 1939. The horrors inflicted by the Nazis painted a brutal and unforgiving picture of the world for a young Harry. Perhaps in response, he used his innate charisma and strong work ethic to defy the Nazis and live a great life, proving that he would never surrender despite their unspeakable crimes. So who is Harry Kaplan? What is Harry all about? In my opinion- Harry Kaplan is King ofWinnipeg’s North End.

<<Previous Article       Next Article >>
Subscribe to the Winnipeg Jewish Review
  • RBC
  • Titi Tijani
  • Jewish Federation of Winnipeg
  • PC Party
  • Sobey's
  • Jewish Federation of Winnipeg
  • Orthodox Union
  • Karyn and Mel Lazareck
  • Booke + Partners
  • Pitblado
  • Accurate Lawn & Garden
  • Coughlin Insurance Brokers
  • Munroe Pharmacy
  • Jim Muir
  • Daniel Friedman and Rob Dalgleish
  • Artista Homes
  • Fetching Style
  • Munroe Dental Centre
  • Cavalier Candies
  • Ronald B. Zimmerman
  • Viscont Gort
  • Safeway Tuxedo
  • Karyn & Mel Lazareck
  • MCW Consultants Ltd.
  • Red River Coop
  • Winnipeg Beach Home Building Centre
  • John Wishnowski
  • John Bucklaschuk
  • Tyler Bucklaschuk
  • Ingrid Bennett
  • Gulay Plumbing
  • Nick's Inn
  • Taverna Rodos
  • Holiday Inn Polo Park
  • Bob and Shirley Freedman
  • Elaine and Ian Goldstine
  • Josef Ryan
  • Western Scrap Metals Inc.
  • CdnVISA Immigration Consultants
  • Simmonds and Associates
  • Doheny Securities Limited
  • Canada Awakening Ministries
  • Fair Service
  • Dr. Marshall Stitz
  • Shindico
  • Astroid Management Limited
  • Piston Ring
  • Commercial Pool
  • Robin Shapiro Photography
  • Broadway Law Group
  • Sorrento's
  • Roseman Corp
  • Laufman Reprographics
  • Equitable Solutions
  • CVA Systems
  • Chochy's
  • Amalgamated Drywall
  • Ambassador Mechanical
  • Renew Mobility
  • Abe and Toni Berenhaut
  • Grant Kurian Trucking
  • Shoppers Drug Mart
  • kristinas-greek
  • The Center for Near East Policy Research Ltd.
  • Sarel Canada
  • Santa Lucia Pizza
  • Roofco Winnipeg Roofing
  • Center for Near East Policy Research
  • Nachum Bedein
Rhonda Spivak, Editor

Publisher: Spivak's Jewish Review Ltd.

Opinions expressed in letters to the editor or articles by contributing writers are not necessarily endorsed by Winnipeg Jewish Review.