Gary joined Edward Jones upon graduation from Wabash College in 1977. Under his leadership, the firm's Morris, Illinois, branch became one of the firm's most successful branches for many years. In the early 1980s, Reamey led the firm's first significant expansion into a major metropolitan area, Chicago. This was a radical departure from Edward Jones' practice of establishing branches almost exclusively in rural areas. This market has served as a prototype for the firm's expansion into the suburbs of many large North American cities. In fact, today 60% of Edward Jones branches are in the suburbs of large cities.
He was named a principal with the firm in 1984. In 1989, Reamey moved to St. Louis, where he was responsible for the U.S. Fixed Income and Trading and Equity Trading areas. In 1994, Reamey spearheaded the firm's international expansion efforts into Canada. This was the first time Edward Jones had opened offices outside the United States. Today, he is the senior principal responsible for the firm's Canadian division. Reamey received an MBA from the University of Chicago in 1987. He serves on the firm's Management and Executive
Committees, is a trustee of Wabash College, a past director for the Investment Industry Association of Canada, a past governor of the Toronto Stock Exchange, a past board member for the Ombudsman for Banking and Investments and a member of the Board of Governors for Junior Achievement of Central Ontario and a member of the Board of Directors for the Community Foundation of Mississauga. Reamey holds dual citizenship in Canada and the United States.