Obituaries
LEO SHEARER
It is with profound sadness that the family of Leo Shearer announces his passing, at the Simkin Centre on November 1, 2019 . Leo lived a long and full life, achieving great success while overcoming many challenges. Words do not do justice to the man Leo was and what he meant to many people. He was larger than life and a true force of nature.
He is survived by his daughters Shelley Shearer-Nelko (Dana), Dr. Ronna Sherman (Joel) and Dr. Brenna Shearer (Stephen). He also leaves behind his grandchildren, Lindsay (David), Riley, Lana, Remy, Hayden, Joshua, Mara, Amy and Sam, as well as his sister Shirley Wasserman, nieces, nephew, great-nephews and nieces and cousins. Leo was predeceased by his parents Sam and Faye Schicher, his infant brother Pesachia and the love of his life, Selma Shearer (Levin) to whom he had been married for 66 years before her passing October 24, 2018.
Leo was born in Mezhirech, Poland on December 12, 1928. His father Sam had to come to Winnipeg alone in 1929, to establish a better life for his infant son Leo and his wife Faye. It was not possible because of Canada’s immigration laws at the time, to bring them to Winnipeg. By the time he found a way to bring them here, Leo was already 6 years old. Growing up in the north end of the city, Leo was determined to make the most of the opportunities his father worked so hard to provide for him in Canada.
A brilliant and hard working student, Leo was one of 3 students at St. John’s Tech to have a grade A average all the way through high school. Although accepted to the prestigious MIT School of Engineering in Boston, he elected to stay in Winnipeg for University in order to help his family, when his father had his first heart attack. Leo graduated from the University of Manitoba with a Bachelor of Commerce Honours degree, where he excelled and was awarded the Eaton Scholarship. Those who witnessed it, described Leo as a mathematical and analytical genius, who could do extremely complex calculations in his head with speed and precision.
After graduation, Leo continued to work with his father at his grain mill, Economy Grain & Feed on McPhillips & Pacific. Although he was accepted to Harvard Business School for post graduate studies, tragedy struck the family. Just as Leo and Selma were expecting their first child, his father had a fatal heart attack at the age of 54. Once again Leo took charge and took care of his family. Eleven years later in 1967, Leo’s world was again changed dramatically by a terrible fire that burned down the Grain Mill. With a wife and three young daughters at home, Leo took this misfortune as an opportunity to redefine himself.
Applying his boundless energy, drive and outstanding business acumen, particularly in the area of finance and real estate development, Leo established his own Mortgage and Development companies. He built numerous projects including nursing homes, apartment complexes and hotels across North America. He was very proud to have been the first to obtain zoning to construct an apartment building on Grant avenue in Winnipeg, called the Americana. Leo alongside his partners, were also ahead of their time when developing the Nursing home called Oakview Place on Ness in St. James, which introduced innovative amenities and features not seen before in senior living facilities.
Time with Leo was memorable for his family and friends. With a terrific sense of humour, Leo truly enjoyed life. A passionate bridge player, he took it seriously achieving Gold Life Master status. He loved golf for many years and long walks outside, as keeping fit was very important him. He travelled around the world with his wife Selma and their many friends. They also loved dancing together, whenever they had the chance. Leo took advantage of the time he had with all of his grandchildren and children, genuinely listening and giving his best guidance and advice. He was there for hockey games, dance recitals and in any other way he could, as he truly loved and felt grateful for the time he had. His father’s untimely death made a huge impact on him. Leo presumed he would die young like his father.
Surviving both prostate cancer and open heart surgery, his strong will, love of life and family was unwavering. Everything he did was to ensure that his family would never have to struggle and worry as he did. His generosity and support was life changing for family members, as he believed in helping whenever he could. After he had surgery for prostate cancer at Johns Hopkins and more recently open heart surgery at St. Boniface Hospital, Leo showed his gratitude with sizeable donations.
Leo’s incredibly sharp mind, fastidious attention to detail and big heart served him well until the end. Diagnosed with vascular dementia in his later years, it became evident that he had a remarkable ability to compensate with his strengths, for a long time as the disease progressed. Through it all, he would say “it’s good to be alive!”. That optimistic bright disposition and perseverance helped him. His physical and mental strength defined him, as he fought and never gave up, when faced with challenges from the beginning of his life until the end.
Leo always made us feel loved and supported. We will miss him greatly and love him forever.
A special thank you to Doris Boutillier his executive assistant for over 20 years, Anastasia, Jessica, Folarian and all of the caring staff at Comforts of Home Care and the Simkin Centre. The love and support from friends and family has been greatly appreciated.
Funeral services will be held on Tuesday November 5 at 12:30 pm, at the Shaarey Zedek Synagogue. Thank you to Rabbi Matthew Leibl and the staff at the Synagogue.
For those who wish to remember Leo, donations can be made to: The Selma and Leo Shearer G.R.O.W. Fund at the Jewish Foundation of Manitoba, 204-477-7520. www.jewishfoundation.org
Obituaries
BARBARA ELAINE WINESTOCK
Barbara Elaine Winestock, maiden name Block, was born on the 27th of May 1951 to parents, Hymie and Gertie Block. She grew up in Hodgson, Manitoba and then Winnipeg’s north end with her parents and younger sister Ava. In short, Barbara was chaos.
In 1980, she married Larry Winestock, who she had met only months prior. When they remembered their plane tickets, the two traveled around the world and when they remembered their luggage, they did so with clothing. They were chronically late, habitually unprepared and perpetually entertaining. Their love was sincere and their fights were like cats and dogs with rabies. Their family would be completed after years of trying to adopt, when they got the “once in a lifetime” opportunity twice, adopting Gabriel in 1989 and Bailey in 1992.
Barbara was so many things to so many people. She did so much throughout her life. She sold advertising spots for CKRC, she taught at the Rady Centre, she sewed, she gardened, she painted and so much more. She was loud, outgoing and made friends everywhere she went.
In 2019 she was diagnosed with brain cancer and given a prognosis of 11 months. This impending date was however not enough to overwhelm her aforementioned chronic lateness. She wouldn’t make this appointment for another six years. She beat it for so long.
Barbara passed away on September 21, 2025. Due to the impending holidays the funeral was held on the 22nd of September at the Shaarey Zedek Cemetery. We miss you Bobs.
Obituaries
KEVIN ROSEN
It is with heavy hearts that we announce the passing of Kevin Rosen, aged 54, on Thursday, December 18, 2025, following a determined and courageous battle with ALS. Kevin was the beloved son of Harvey Rosen (z”l) and Judy Goodman, loving husband of Judi Price-Rosen, devoted father of Emery, cherished brother of Pam, and special brother-in-law of Barbi and Jared Green. He was also the proud uncle of Stella, Jakob, Miranda and Micah, a treasured cousin, and a loyal friend to so many.
Kevin was born in Winnipeg and grew up in Garden City where he attended Talmud Torah, Jefferson Junior High and Garden City Collegiate. He graduated from the University of Manitoba in 1996 with an Honours degree in Commerce and soon after, headed to Toronto. It was there that he met the love of his life, Judi, and they married in 2000. Soon after their wedding, the newlyweds returned to Winnipeg to start their new life together. For 25 years, their love for each other remained unwavering and strong. Kevin’s calm demeanor and his remarkable ability to find humour in any situation helped them weather life’s challenges together.
In 2006, Judi and Kevin became a family with the birth of their son, Emery. Kevin’s greatest joy was being a dad and fatherhood came naturally to him. He parented with patience, empathy and gentle guidance. Whether it was watching cartoons and funny TikTok clips together, or a surprise trip to Toronto to take in a Blue Jays game, Kevin always made “father-son time” a priority.
Kevin had a long and successful career in marketing and communications that began in Toronto, and continued in Winnipeg at Gateway Publishing. Most of his employment experience was in higher education. He was hired as Marketing Manager at Red River College in 2004, and in 2012, reached the pinnacle of his career as Executive Director of Marketing and Communications at the University of Winnipeg. Kevin led with integrity and humility and genuinely cared about the people he supervised. He was respected and well-liked by his colleagues and many remained in close touch after his early retirement.
Kevin was also an avid runner who completed seven full marathons. For years, he had trained his body and mind to push through that last gruelling mile with tenacity and intense focus. Like his favorite movie hero Rocky Balboa, Kevin was built for an epic fight. Little did he know that in his case, the stakes would be so much higher. The fight of Kevin’s life – and for his life – began with a diagnosis of ALS just months before he turned 50.
ALS may have changed his life, but Kevin never let it define him. He remained fiercely independent, continued to nurture relationships with family and friends, and welcomed visitors with a playful smile, a joke, and incredible patience. Even after he lost the ability to speak, Kevin’s quirky sense of humor remained, shining through via text, his computerized surrogate voice, and that signature glint in his eyes.
He was kindness personified. A wonderful listener. Loyal. Thoughtful. Humble. A true mensch.
To paraphrase his late father, we all won the lottery of life for having had the privilege of knowing and loving Kevin Rosen.
The family extends their heartfelt gratitude to the many doctors, nurses and specialists involved in Kevin’s care: the staff at the Motor Neuron Clinic, his WRHA Palliative Care Team, Diana at the ALS Society of Manitoba, “Smoky” Lisa and Brenda. Sincere appreciation to Harsh, Maggie, Avya and Harleen who honoured Kevin’s dignity and provided companionship at the most difficult stage of his illness.
Donations in Kevin’s memory can be made to the ALS Society of Manitoba or the University of Winnipeg.
A Celebration of Life is planned for the spring of 2026.
Obituaries
ALAN LEVY
On January 6, Alan Levy, age 71, died at Grace Hospital with his wife and daughters by his side.
Born and raised in Winnipeg, Manitoba, Alan spent his childhood in the North End and later moved to River Heights, where his family settled on Brock Street.
After studying in Winnipeg and Tel Aviv, Alan moved to Toronto, where he lived for over 30 years. It was in Toronto where he raised a family with his first wife, Sylvia Bashevkin, worked in public sector human resources and fell in love with Chinese food.
In 2017, after brief stints as an academic in Regina and Brandon, Alan moved back home to the Peg, where he spent many fulfilling years with his devoted wife of 20 years, Cheryl Karlinsky, and their loving dogs. In his later career, he was appointed to the Labour Relations Board of Canada where he served as a skilled adjudicator and proud Canadian.
Alan was endlessly proud of his family, daughters Dalia Levy and Aviva Levy (Adam Walman) of Toronto, and two grandsons, Jonah and Ethan.
Predeceased by his parents Sheldon and Audrey Levy (nee Myers) of Winnipeg, Alan was a dedicated news junkie with a sharp sense of humour. He thrived most when discussing current events, cracking jokes and debating geopolitical crises. Much to his family’s frustration, he would stay up all night glued to the news, and they’d wake up to endless articles he’d shared the night before.
Alan had an exceptionally strong spirit of generosity and focus on ‘tikkun olam’ – repairing the world, which lives on in his children and grandchildren. His family is grateful to the staff at Simkin for providing him with a phenomenal level of care over the last few years, especially Dr. Chung and Sara Reid, Assistant Director of Care. Special thanks to Paul, Victor and Almaze, his kind and patient caregivers.
The funeral took place at Chesed Shel Emes on January 8.
Donations in his memory can be made to The Saul and Claribel Simkin Centre https://www.simkincentre.ca.