Sears Canada, a retail giant with a long and successful history used to employ as many as 56.000 full-time and part-time associates across the country. With reported total revenues hovering at $ 6.356 billion in 2000, Sears used to be Canada’s largest full-line retailer of general merchandise and home-related services. The company was comprised of 118 Sears department stores, 7 urban dept. stores and as many as 37 furniture and appliance stores. In addition, Sears had 131 dealer stores, 15 outlet stores, 38 floor covering centers, 66 auto centers and 108 travel offices. Sears used to offer a number of services, such as appliance maintenance programs, insurance travel, et.al. The company ultimately filed for bankruptcy on 6/22/2017. The purpose of this report is to explore what company’s record tells us about the strategic actions it managed to undertake. We are going to look into the key elements behind Sears Canada’s downfall. The focus is on the specifics of the retailing industry in Canada by assessing and re-assessing the drive factors, competitive forces and main mistakes and omissions, committed by Sears’ management. We’ll also try to understand key shortcomings and errors committed by Sears, analyze them and make sure to avoid them in real-life situations. We are also going to assess the Canadian retail market and take a close look at the driving forces behind it (knowing that the younger population in Canada have resorted to e-commerce, whereas the older generation is finding it somewhat difficult to catch up) – a classic case of generation gap.