He was previously wide receivers coach and passing game coordinator for the Edmonton Elks of the Canadian Football League (CFL).

He played college football at the University of Richmond and attended Gar-Field Senior High School in Woodbridge, Virginia.

[4] October spent the 2001 offseason with the Washington Redskins of the National Football League after signing with the team in April 2001.

The following offseason offensive coordinator Jaime Elizondo left the team which expanded Winston's role for the 2019 season to include the responsibility of play calling.

[6] On January 15, 2020, it was announced that October had joined the Edmonton Elks as the team's receivers coach and passing game coordinator.