This elite travel baseball team regularly competed in tournaments across North America, and was composed of the top young players in all of Ontario.

[12][13] Naylor played in 25 total games for the Marlins posting a .327 batting average with one home run and 16 RBIs.

[14] In June he was suspended without pay after injuring teammate Stone Garrett with a knife as part of a prank.

[16] On July 29, 2016, the Marlins traded Naylor, Carter Capps, Jarred Cosart, and Luis Castillo to the San Diego Padres in exchange for Andrew Cashner, Colin Rea, Tayron Guerrero, and cash considerations.

[26] Naylor made appearances for San Diego in 2020, batting .278/.316/.417 with one home run, four RBI, and one stolen base.

On August 31, 2020, the Padres traded Naylor, along with Austin Hedges, Cal Quantrill, and minor league players Gabriel Arias, Owen Miller, and Joey Cantillo, to the Cleveland Indians in exchange for Mike Clevinger, Greg Allen, and Matt Waldron.

[27] In the 2020 American League Wild Card Series, Naylor recorded five hits in his first five career postseason plate appearances, the first player in MLB history to do so.

[28] During a game against the Minnesota Twins on June 27, 2021, Naylor collided with second baseman Ernie Clement while trying to catch a pop up in shallow right field.

[32] On January 13, 2023, Naylor agreed to a one-year, $3.35 million contract with the Guardians, avoiding salary arbitration.

[2] He profiles as a power hitter,[4] and Greg Hamilton, the coach of the Canadian national junior team, described Naylor's hitting approach as "advanced".