Driving force behind Cubs' expanded footprint in Japan is set to join the Yankees

For much of the last decade, the Chicago Cubs have made a concerted effort to expand their footprint overseas, especially in Japan. That's translated to the big-league roster, first with the signing of right-hander Yu Darvish, already an established and decorated MLB presence at the time, then deals with slugging outfielder Seiya Suzuki and left-hander Shota Imanaga.

A driving presence behind the team's push to become a major player in Japan, Nao Masamoto, was a staple at Wrigley Field for decades, dating back to 2005. He was part of the teams that pitched both Suzuki and Imanaga - not to mention the Cubs' respective pitches to Shohei Ohtani and Roki Sasaki. After the 2025 season, he decided to explore new opportunities and, according to The Athletic (subscription required), the New York Yankees are planning to add him to their front office.

Longtime Cubs executive poised to join the New York Yankees after helping Chicago land Seiya Suzuki and Shota Imanaga in recent years

New York, once a prime destination for Japanese stars looking to make the jump to the U.S., wants to re-establish itself as a landing spot after missing out repeatedly in recent years on players like Ohtani and Yoshinobu Yamamoto. Their hope is Masamoto can help them do that.

To this day, Darvish has nothing but praise for the Cubs - a testament to the team's efforts to help him acclimate to his new environment back in 2018. That relationship may not seem that important now, especially considering the five-time All-Star may have thrown his last pitch, but Darvish maintains a vaultred standing among Japanese players.

The signing of Suzuki prior to the 2022 season marked a major international addition for Chicago. With each passing year, his numbers, particularly in the power department, have improved. He's coming off a 32-homer, 103-RBI campaign in 2025 heading into the final year of his contract and has an important role to play in the wake of Kyle Tucker's departure in free agency this winter.

Imanaga burst onto the big-league scene in dramatic fashion in 2024, finishing fourth in NL Rookie of the Year voting and fifth in Cy Young balloting after turning in an impressive 2.91 ERA across 173 1/3 innings of work. A hamstring injury caused mechanical issues (that translated into an inability to keep the ball in the yard) last year, but after returning via a qualifying offer, the southpaw will look to get back on track in 2026.

Really, all teams - from the Yankees to the Cubs and many others - are simply looking to narrow the gap between their organizations and the reigning back-to-back champion Dodgers, who have become a juggernaut in their pursuits of Japanese players. Their roster now includes the likes of Ohtani, Yamamoto and Sasaki - a formidable trio ready to help Los Angeles to chase down a third-straight title, something baseball hasn't seen since the Yankees did it from 1998-2000.