Jim Naylor, a former high‑school baseball coach in Mississauga, Ontario, built a reputation for nurturing talent and emphasizing fundamentals. He coached local youth leagues for over two decades, fostering a disciplined yet supportive atmosphere. Sandra Naylor worked as a school administrator, balancing academic responsibilities with family life and encouraging her children to prioritize education alongside athletics. Their partnership combined sport‑centric mentorship with academic rigor, creating a balanced upbringing for Josh and his older brother, Bo, who also reached the major leagues.

The Naylor household emphasized community involvement; weekend games often turned into family outings, and local charities received regular support. Jim’s coaching philosophy stressed respect for teammates and resilience after setbacks, while Sandra’s focus on structured study routines helped the brothers manage schoolwork during demanding training seasons. This blend of athletic guidance and academic encouragement is widely cited as a cornerstone of Josh’s steady rise through minor‑league ranks to the MLB.