Jack Winnay, a native of Newton, Massachusetts, is working toward his goal of becoming one of the few local players to rise through the Boston Red Sox system and reach the major leagues. The 23-year-old first baseman and outfielder was selected by the Red Sox in the 13th round of the 2025 MLB draft after a collegiate career at Wake Forest marked by significant power-hitting achievements.

Winnay, who attended Belmont Hill School before playing three seasons with the Demon Deacons, hit 20 home runs as a sophomore and 15 as a junior. Despite considering his final college season a disappointment, he made a clear decision with his agent to turn professional only if it was with the Red Sox, citing both the club’s player development system and his lifelong dream of playing for his hometown team. Boston fulfilled that aspiration by signing him with a $150,000 bonus.

Since joining the organization, Winnay has begun adapting to professional baseball through the Red Sox farm system. After a slow start to his first full season, he has shown significant improvement in the High-A Greenville Drive, where he posted a batting line of .318/.487/.682 with 10 home runs over 27 games spanning early May to mid-June. He has demonstrated a disciplined approach at the plate, drawing more walks than strikeouts during this period, particularly excelling against left-handed pitchers.

Standing 6-foot-3, Winnay has harnessed his strength in pulling the ball in the air, capitalizing on Greenville’s Fluor Field, which mimics the iconic Green Monster wall of Fenway Park. His approach, refined with an emphasis on increasing bat speed, has seen his average swing velocity rise from 69 mph to 71 mph since signing, approaching the big-league average of 72 mph. Winnay credits his ability to focus on favorable pitches early in counts and a patient philosophy at the plate for his rising on-base percentages and power numbers.

In addition to batting, Winnay has been developing defensively, transitioning from a first baseman and outfielder in college to trying his hand at third base in the minors. His preparation has been bolstered by working out alongside fellow Massachusetts natives and Wake Forest alumni Shane Smith and Jared Shuster, both of whom have reached the majors.

Winnay’s connection to Boston goes beyond the field. Growing up attending Fenway Park games, moments such as encountering Red Sox legends David Ortiz and Pedro Martinez during spring training have reinforced his dedication. Now playing in Greenville, where “Sweet Caroline” is played during games and the Green Monster stands, Winnay feels a tangible link to his ultimate goal.

"I’m truly grateful," Winnay said. "It really feels like there’s a real path to Fenway, and like I’m playing in front of a Boston fan base. It feels super special putting that jersey on every day."

As Winnay continues to advance through the Red Sox system, he aims to join the rare group of Massachusetts-born and developed players who have worn the red jersey in the majors—a tradition not seen since Alex Hassan’s brief stint in 2014. His ongoing progress highlights the potential of a hometown talent working to fulfill a lifelong dream.