Former Cubs director of pitching Ryan Otero is leaving the organization to join the Red Sox as a special assistant to the chief baseball officer, league sources told the Sun-Times.
Tyler Zombro, who for the past year served as a Cubs special assistant with a focus on pitching, is set to take on a larger role that will include oversight of the minor-league pitching department, according to sources. His exact title is not yet formalized.
Otero reunites with Red Sox CBO Craig Breslow, who served as a Cubs assistant general manager and the senior vice president of pitching before taking the top baseball operations job in Boston.
Otero was Breslow’s right-hand man as he overhauled the Cubs pitching infrastructure. In the wake of Breslow’s departure, Otero served as pitching director for two years.
This past year, Zombro brought his experiences from the private sector, specifically Tread Athletics, to work with the major-league pitching staff, alongside the team’s pitching coaches.
He lent his expertise to the front office as well, doing deep dives on available pitchers. One of his biggest wins was right-hander Brad Keller’s breakout season. Zombro played a key role in identifying Keller as a target, recruiting him, and assisting in his development.
A former starter and swingman, Keller went from minor-league free agent to one of the Cubs’ most trusted high-leverage relievers last season.
Zombro, 31, was on the mound himself as recently as 2023. He spent six seasons in the Rays’ farm system.
