High School
Cuddyer was born in Norfolk, Virginia and is a 1997 graduate of Great Bridge High School in Chesapeake, Virginia, where he was a standout athlete in baseball, basketball, and football. Cuddyer was named Virginia's Player of the Year and Gatorade National baseball Player of the Year in 1997. He was also a member of USA Today's All-Star and the USA Junior National teams in 1997.
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