Josh Naylor competed at Cooperstown Dreams Park three times. His first two appearances were with the Mississauga North Tigers (CAN) during Tournament 11 in 2008 and Tournament 8 in 2009. His final trip was with the Canadian Beaver Tails (CAN) during Tournament 5 in 2010. Josh helped the Canadian Beaver Tails post a 5-1 pool play record and reach the Sweet 16.

Josh, a first baseman, graduated from St. Joan of Arc Catholic Secondary School (Mississauga, Ontario). He did commit to continue his education and play baseball at Texas A&M University (College Station, TX), however, he made the leap to the professionals when he was drafted as the 12th pick overall by the Miami Marlins during the 2015 Major League baseball draft. Josh was traded to the San Diego Padres in 2016. He made his Major League debut on May 24, 2019.

On August 31, 2020, Josh was traded to the Cleveland Guardians. Josh and the Guardians clinched the 2024 American League Central division.

Josh was traded to the Chicago Cubs on December 7, 2024.