July 24, 2025
Former Belmont Hill standout Jack Winnay ‘22 reached another incredible milestone in his baseball career when he was drafted by the hometown Boston Red Sox in the 13th round of the 2025 MLB Draft with pick number 388.
In his time at Belmont Hill, Jack earned four varsity letters, won a League Championship and was named First Team All-ISL, First Team All-NEPSAC, 2022 ISL Hitter of the Year, and Perfect Game First Team All Northeast. The accolades only tell part of the story of Jack’s impact on the program and his teammates.
“Jack was not only one of the most talented players to come through the program, he also is just a fantastic human being and a tremendous leader,” said former head coach Mike Grant who led the team during Jack’s career at Belmont Hill. “Teammates loved his competitive but also fun loving nature, and steady leadership presences. He has all the tools, physical and mental, to play in Fenway Park someday.”
The entire School community congratulates Jack on this remarkable achievement and looks forward to following his journey with the Red Sox organization.
