When he first stepped onto the UMass Boston campus Nao Masamoto had only lived in the United States for a year after his family's migration from his native Japan and could not speak English very well, but he could play baseball extremely well. The middle infielder made the Beacon nine as a walk-on during his freshman season and soon became the team's starting shortstop, while setting school-records for at-bats and assists in a season and ranking second on the squad in hits, runs scored and stolen bases. Masamoto was even better as a sophomore, leading the team in hits, runs, total bases and on-base percentage, while establishing a new school-mark with 25 stolen bases, which ranked second among Little East Conference players. Following an arm injury, the Japanese import was relegated to a designated hitter role and excelled, with a .336 batting average, which led to his distinction of becoming the first player in school history to be selected as a Little East Conference First Team All-Star. He matched the feat a year later in his second year as the team's captain when he was named to the LEC First Team as a second baseman after ranking third among the league's leaders with a then school-record .425 batting average. Masamoto also placed among the league's top five in hits, runs scored and stolen bases, while maintaining a .455 on-base percentage. He finished his career as UMass Boston's career leader in at-bats (533), runs (124), hits (177), stolen bases (60) and times being hit by a pitch (21), while standing 10th with a career batting mark of .332. Masamoto also ranks second with 138 games played, 91 runs batted in, 30 doubles, 47 bases on balls, 236 total bases, seven triples and 266 assists. Following his 2001 graduation from the Harbor campus, Masamoto secured stints with Major League Baseball's Colorado Rockies and Chicago Cubs as their minor league strength and conditioning coordinator before taking on his current role as the Cubs' major league video coordinator.