Naylor attended St. Joan of Arc Catholic Secondary School in Mississauga, Ontario, and played for the Canadian junior national baseball team.

[1] He appeared in the Under Armour All-America Game and the Under-18 Baseball World Cup held in Ontario in 2017.

[4] The Cleveland Indians selected Naylor in the first round, with the 29th pick, in the 2018 Major League Baseball draft.

[10] Naylor did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.

[15] He made his major league debut the same day against the Kansas City Royals as a defensive replacement.