Naylor’s baseball journey began at St. Marcel Catholic High School, where his power at the plate earned him a reputation as one of Canada’s top prospects. The Cleveland Guardians selected him fourth overall in the 2018 MLB Draft, and he spent the next two seasons honing his skills with the Lake County Captains and the Akron RubberDucks, rapidly advancing through the minor‑league ranks.
His major‑league debut arrived on September 2, 2020, and the following seasons saw him transition from a bench player to a everyday outfielder. The 2022 campaign marked a breakout year, as he posted a .269 average with 20 home runs and solidified his spot in the lineup. By 2024, Naylor had become a consistent contributor, known for both his offensive upside and defensive versatility.