Defeated along with the St. Laurent government in the 1957 election, Winters entered the corporate world, becoming a chief executive officer at a series of companies. He was hired as a special advisor to the Newfoundland government to help negotiate the Churchill Falls deal, for which he became highly popular in that province.
He was persuaded to return to politics by Lester Pearson, and won the Toronto seat of York West in the 1965 election, becoming minister of trade and commerce in Pearson's government. He was seen as close to the business community and far more fiscally conservative than Walter L. Gordon. He originally announced that he would not seek to replace the retiring Pearson, but changed his mind and ran to succeed Pearson at the 1968 Liberal leadership convention, coming in second to Pierre Trudeau.
Winters then left politics, to become president and director of Brazilian Light and Power and a vice president of CIBC. Also, he was very involved in the new York University and served as the first chair of its board of governors.
Death
In 1969, while in California, he suffered a heart attack during a game of tennis. He died at age 59 in an ambulance on his way to hospital.
