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.

Alexander is from the Sifton family. Alex received his Bachelor of Social Sciences (Honours) with Major in Criminology and a Minor in Psychology from the University of Ottawa in 2020.