Ruby began his football career with Medway High School, near London, Ontario, before moving to Fork Union Military Academy where he was an All-Prep League player.

[1] In 2012, Ruby and the Spiders won a share of the Colonial Athletic Association conference championship, but were snubbed from a playoff spot.

Ruby was selected in the first round, eighth overall, in the 2015 CFL Draft by the Montreal Alouettes and signed with the team on May 27, 2015.

[5] Shortly after his release from Montreal, Ruby signed with the Edmonton Eskimos on July 17, 2017, and played in two games during the 2017 season.

[7] He played and started in the first three regular season games for the newly named Edmonton Elks in 2021, but was released on August 31, 2021, due to a violation of COVID-19 protocols.

[8] Ruby reportedly misrepresented his vaccination status to the Elks and was subsequently barred from signing with any CFL teams for the remainder of the 2021 season.