Purpose – The purpose of this paper is to review the evolution of the Canadian financial environment since the stock market “crash” of 1987. Design/methodology/approach – The paper provides a chronological account of significant events in the Canadian economic environment and capital markets, and how they have transformed the financial climate. Findings – The late 1980s was a turbulent period with many changes in government and economic policies which were initiated at a time when governments were wracked with fiscal deficits, and just as the central bank appointed a dedicated inflation fighter. These changes worked their way through the system to contribute to one of the worst recessions in Canadian history. One of the symbols of disparity during this era was the Stock Market “Crash” of 1987, which was felt in Canada, as well as around the globe. However, for the last decade, the federal government has reported a surplus every year, and Canadians have benefitted from falling tax rates, declining interest rates, a strong stock market, and a rising currency. In fact, until September of 2008, all of these developments had contributed to unprecedented profitability in the financial services industry, until the recent widespread economic crisis in the US spread to Canadian and global economies. However, the Canadian economy seems much better poised to deal with such adversity than it was in October 1987. If the fall of 2008 is any indication, we will find out soon enough. Originality/value – The paper demonstrates how fallout from the crash of 1987, as well as other subsequent developments, has contributed to significant changes in the financial environment.