Maddox graduated from high school in 2009 as the top catcher in the state of Florida, having batted .544 in his senior year. He was drafted by the Tampa Bay Rays in the 37th round of the 2009 MLB Draft, but he did not sign. Instead, he played college baseball at the University of Florida, where he was teammates with future MLB catcher Mike Zunino. Initially a catcher and infielder, Maddox batted .303 in his three seasons with the Gators (2010–2012). In 2011 and 2012, he made a total of 53 appearances as a pitcher, striking out 78 and walking 14 in ​82 1⁄3 innings, while compiling a 1.86 earned run average (ERA).\n', '

Maddox was drafted by the Boston Red Sox in the third round of the 2012 MLB Draft, and signed with the team in June 2012.\n', '

From 2012 through 2015, Maddox played in the lower levels of Boston\'s farm system; the Rookie League Gulf Coast League Red Sox, the Class A Short Season Lowell Spinners, the Class A Greenville Drive, and the Class A-Advanced Salem Red Sox. During 2016, he was promoted to the Double-A Portland Sea Dogs and then the Triple-A Pawtucket Red Sox. In 2017, he again played in Portland and Pawtucket, and was called up to the majors for the first time on June 15.\n', '

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