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Naylor’s journey included competing for the Ontario Blue Jays and Canada’s Junior National Baseball team, where he made headlines during a home run derby and faced severe adversities, like being stranded in Mexico during Hurricane Odile. After being drafted 12th overall by the Miami Marlins in 2015—becoming Canada's highest and youngest MLB draftee—Naylor’s career faced various hurdles, including a messy incident involving a knife prank that led to his trade to the San Diego Padres.