Advanced Search:

Regular Search
❮ Go Back to Listings


Born: Feb 12, 1944

Date of Passing: Apr 07, 2020

Send Flowers to the Family Offer Condolences or Memory

Adjust Text Size: A+ A-

February 12, 1944 - April 7, 2020

Survived by the love of his life, Leslie; children, Jon (Monique), Rob (Elisabeth), Erica (Colin); and eight grandchildren, Aliya, Eric and Kyra, William and Elin, Kiefer, Annika and Callen. Also, his sister Lynn (Doug); brothers, Mark (Debbie), Leif (Susan) and sister Ingrid. Along with sisters-in-law, Joanne Leven (Len) and Heather Watt; in addition to his many nieces and nephews.
Bill exhibited academic and leadership skills throughout his school years culminating in being awarded the Governor General's medal in his last year at Nelson McIntyre Collegiate in Norwood. He also served as President of the student body and took leading roles in the operettas. This love of music continued throughout his life. His passion in these early years was basketball and all his spare time was spent on a court.
Bill's life changed dramatically when he started University. He worked in Wood Buffalo National Park, NWT in the summer months where he learned carpentry skills and toiled as a labourer in the bush. In those five summers he became sufficiently proficient which allowed him to spend many spare hours, later in life, renovating and adding on to the family cottage acquired at Falcon Lake.
Bill started his lifelong relationship with Leslie in 1964, ultimately marrying in 1967. Their beloved children became the focal point of their lives from 1972 to the mid nineties. Bill spent many hours coaching Jon and Rob in hockey, and Erica in ringette.
After marrying Leslie in 1967, Bill entered the Faculty of Law at the University of Manitoba, graduating with the Gold Medal in 1970. Many close friends were made in these years and these relationships continue to this day. While in Law School, Bill developed a lifelong fascination with litigation and he and Leslie spent 1970 to 1971 in Ottawa while Bill clerked for a Supreme Court Justice. These early exposures only enhanced his career choice and he became a well known and highly respected litigator in not only Manitoba, but throughout Canada. Bill was competitive to a fault, whether in sports or the practice of his profession. He most enjoyed providing advice and service to those who were front line workers such as the police, teachers and healthcare workers. He was motivated to help those who suffered at the hands of the more powerful.
Bill believed fervently that litigation was an art form which required mentorship to perfect the applicable skills. Accordingly, he mentored several years under A. Kerr Twaddle and then under Vern Simonsen. In so doing, he began to practice what he preached and assisted many young lawyers to develop their skills similarly. It was with sheer pride that those who worked with him became excellent lawyers, many of whom continued to work in the law firm with him for many years.
Bill also believed it was the responsibility of a professional to give back to the profession. In 1986, he served as President of the Law Society of Manitoba. Over the years he spent many hours participating in lectures to the profession. He became known as being highly intelligent, fair to all he encountered and an unparalleled tactician.
For a number of years, Bill helped manage TDS and was appointed counsel to the firm for the last ten years before his retirement.
In later years, he served on the Board of Manitoba Blue Cross, developing more understanding of corporate life and making many close friends outside of the legal community.
While he shone academically and achieved much professionally, Bill would tell all that his life was best defined by his undying love for his wife Leslie, and their children, Jon, Rob and Erica. All his achievements were made possible by, and ultimately for, Leslie, who kept him appropriately grounded. They truly enjoyed each other's company, travelled much and befriended many.
To have children and to devote one's life to their development as mature adults is an unparalleled calling. Bill's life, outside of the practice of law, was centred on their children's needs and interests, and the pride and love Bill and Leslie had for Jon, Rob and Erica continued for all their lives. Their intelligence, honesty and sense of humour were more than Bill could have hoped for. His three children, their spouses and eight grandchildren were always truly the light of his life, enabling him to pass on with the certitude of each continuing their development into caring and contributing members of their community.
Bill was sensitive, caring and fun loving. His Golden Retrievers loved him unconditionally and he reciprocated. Many days were spent every year at the cabin at Falcon Lake and Bill valued the opportunities there to practice carpentry and to pass on his love for cottage life. Many hours were spent imparting some life lessons to his children and grandchildren. Many friends visited there over the years and that camaraderie was cherished.
While verbalizing his love for his wife, family and many friends did not come easy for him, Bill tried to convert his feelings through his actions. He was rewarded more than was due. He is passing with the comfort of this reciprocal love of his wife, children and grandchildren, and many friends.
Bill would also be remiss to not mention his deep gratitude for the sense of humour and dedication of Dr. Ken VanAmeyde, Head of Internal Medicine at the Health Sciences Centre, and his advice and care over the last few years. Ken always exhibited those traits of professionalism to which all professionals should aspire. His friendship was most appreciated.
Given the current COVID-19 pandemic restrictions, a Celebration of Life will be held later this year.

For those who wish to sign the online
Guest Book please visit

Chapel Lawn Funeral Home

As published in Winnipeg Free Press on Apr 11, 2020

Condolences & Memories (10 entries)

  • Dear Leslie and family, our deepest condolences on the loss of Bill. Bill was my Bridge partner in our early University days at UMSU. Not a better player to be found. He truly was an amazing person. Although I have not seen him in many years he will always be fondly remembered. John Wiebe, West Vancouver - Posted by: John Wiebe (Friend) on: Apr 24, 2020

  • Dear Leslie & family. My sincerest condolences in the loss of Bill. Our sporadic visits over the years were memorable and always fun!! Take care. - Posted by: Sally Bracken (Carrick) (Friend) on: Apr 20, 2020

  • To the Olson family, We are very sorry for your loss and hope you find comfort in the lifetime of memories and in your family and friends. Wishing you all the best, The Cherewick Family - Posted by: Derek Cherewick (Family Friend) on: Apr 15, 2020

  • My most sincere condolences to the Olson family. These last few years must not have been easy and I hope you each find some peace in the days, weeks and months ahead. I came to know Bill through his work with Jack Haasbeek and the police association. The two of them could not have been more like minded nor better paired as a team. Bill's long tenure representing our association gave me opportunity to experience, first hand, much of how Bill has been described; incredible tactician - patient & encouraging mentor - absolutely competitive to a fault (good for us!) - a sincere dedication to ensuring frontline members were not trod upon - and very definitely an artist in his chosen craft...his cross examinations and summations were the stuff of the very finest most genuine theatre. I am thankful I knew Bill in the circumstances I did. There is no question Bill's interest in my interest in representative advocacy, contributed significantly to the approach, enthusiasm and strategical bent I would adopt on behalf of our associations members. I am grateful to have worked with Bill and more importantly, to have known him as a friend. My sincerest condolences...Bill was a wonderful human being... - Posted by: Marc Pellerin (Friend) on: Apr 14, 2020

  • Leslie, Jon, Erica and Rob. My heartfelt condolences on the loss of Bill. Dorothy and I always counted ourselves fortunate to have had you and Bill and your beautiful family as neighbours in the seventies and eighties and to have our three boys grow up with your three children. We shared many memorable times as neighbours , hockey parents, and friends at parties and at Southdale community club. I always had a great respect for Bill for his intellect and ability to present a reasoned perspective. Bill had a serious demeanor, but knew how to live and to let loose and party. His Bird dance and YMCA dance were proof that Bill had a fun side. All our love at this difficult time. Bob,Sean,Craig and Ryan Savage. - Posted by: ROBERT SAVAGE (Nighbour and friend.) on: Apr 12, 2020

  • Leslie and family, Sending all my sincere condolences at this time of such great loss. I have many fond memories of the Southdale times with hockey parents and parties. Bill was always the life of the party and truly a special man. He will always be remembered with great fondness. - Posted by: Suzette Lacroix (Family friend) on: Apr 12, 2020

  • Condolences to Bill's Family. I knew Bill through his being the Winnipeg Police Association lawyer who was instrumental in helping us achieve one of the best Collective Agreements a unionized worker could ever hope for. As a former member of our negotiating team I was and continue to be in awe of Bill's work ethic, knowledge for doing the right thing and most of all his sense of humour displayed when times seemed dark....he stood tall but never let his stature over shadow the little guy...if God needs a great negotiator he has the best in his fold now...Mike Ewatski and Family - Posted by: Mike Ewatski ( Acquaintance ) on: Apr 11, 2020

  • Dear Leslie and family- We are so sorry to hear of the passing of our dear friend, Bill Olson! I spent a full year with Bill when he was a student at Pitblado, Hoskin,in 1969. Even then, very early in his career (he had just won the gold medal in his class at Law School), Bill was one of a kind. He cared not only for the law of a case, he saw how important the facts and personalities were! When he went to Ottawa for a year at the Supreme Court, it gave his fine mind the opportunity to encounter the real world of the law. After he returned, I will always remember Bill quoting from Mr. Justice Holmes saying "the life of the law is not logic, it is experience". In retrospect, It dictated too, how he related to people. While Bill had much to be boastful about (he won many landmark cases in his career), he was very self-effacing, and it was this trait that many found most attractive about him, since he was always there for the most powerful and the downtrodden. Bill will be forever remembered as a good friend and fine human being. We look forward to hearing more about him at the Celebration of Life! Abe Anhang - Posted by: Abe Anhang (Colleague) on: Apr 11, 2020

  • Dear Leslie and family. My heart breaks at the news of Bill's passing. Please know that being his legal assistant for 35 years was a great experience and having Bill's trust and respect meant so much to me. I'm glad I was able to visit both of you just before last Christmas. My condolences to you and your family. He will be forever remembered and missed by all who knew him. But he leaves his legacy with your family and anyone who had the privilege of working with him. Sending you hugs, love and prayers of support at this time. Sincerely, Verna Kakowchyk - Posted by: Verna Kakowchyk (Friend and was his legal assistant for 35 years) on: Apr 11, 2020

  • Dear Leslie and family. Joanne and I are truly saddened to learn of Bill’s passing . He was an amazing person and admired by many. His intellect, discipline and ethical base has been admired and will be missed by many. We are reminded of the wonderful days we all spent together during our law school days and afterwards as we pursued our legal professions. He will be fondly remembered . David & Joanne Unruh West Vancouver, BC. - Posted by: David and Joanne Unruh (Friends ) on: Apr 11, 2020

Chapel Lawn Funeral Home & Cemetery

Chapel Lawn Funeral Home & Cemetery

4000 Portage Ave. (Map)
Ph: 2048859715 | Visit Website

❮ Go Back to Listings