Winfield is from the Sifton family that founded an empire in the Canadian newspaper publishing and broadcasting industry and other renowned business enterprises. He attended Lakefield College School alongside European Royal families and outstanding Canadian business families, and received his Honours in Economics from Queen’s University.
In 1982, Winfield became the President of Worldwin. Winfield together with his network of advisors were responsible for all investments of Worldwin covering a wide geographical range. While very active in Canadian businesses in addition to a well respected real estate developer, Winfield also sat on numerous boards including Lakefield College School’s Board of Governors. Winfield is also the President of the Armagh L. Sifton Charitable Foundation.