"As the Cubs welcomed players from Nippon Professional Baseball - and managed relationships with their families, agents and support staff - Masamoto's background provided some credibility and reassurance. Masamoto enjoys a strong relationship with Yu Darvish, who played for the Cubs and remains an influential figure among Japanese players. Darvish recommended Chicago - as a city and an organization - to Seiya Suzuki before the outfielder/designated hitter signed his five-year, $85 million contract with the Cubs in 2022."
"Masamoto was also part of the group that helped Shota Imanaga quickly assimilate in 2024, when the left-handed pitcher received National League Cy Young Award and Rookie of the Year votes. The decision to separate, as far as the Cubs go, sounds like it was on Masamoto's side (he "elected to explore his options and see what new opportunities might arise from the sport's influx of Japanese talent" after the season)."
Nao Masamoto spent about 20 years with the Cubs and became a central connector for Japanese players, their families, agents and support staff. His background and relationships provided credibility and reassurance to Nippon Professional Baseball imports. Masamoto maintained a strong bond with Yu Darvish, who recommended Chicago to Seiya Suzuki before Suzuki’s five-year, $85 million deal in 2022. Masamoto helped Shota Imanaga quickly assimilate in 2024, contributing to Imanaga receiving National League Cy Young Award and Rookie of the Year votes. Masamoto elected to explore new opportunities after the season, and the Yankees are reported to be adding him to their international staff, reducing the Cubs’ in-country continuity in Japan.
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