Jack Winnay’s summer started as a college student, member of the Wake Forest University baseball team. He’s now a professional baseball player, Boston Red Sox Organization, and off to a fantastic start.
The 22-year-old Newton native made his professional debut with the Salem Red Sox, collecting five hits in seven at-bats, and reaching base in seven of his first nine plate appearances across two games for the Single-A Affiliate of the team he grew up rooting for.
“I’ve always wanted to just play in the major leagues,” Winnay said in an interview following his selection in the 13th round (388th overall) of mid-July’s Major League Baseball Draft, “and to be able to have a chance to do it for the Red Sox is even more motivation.”
His childhood bedroom still has the Red Sox posters and jerseys he collected as a kid.
“It’s surreal, and he’s been so focused on this dream forever, so in some ways it makes sense,” said his mother, Sarah Stephens Winnay. “For me and [Jack’s father] Jon, we’re so happy to see him and his hard work coming true.”
Following his selection, Winnay quickly reported to the team’s spring training facility in Fort Myers, Florida, signed a contract — including a $150,000 signing bonus — and trained for a couple weeks before packing his bags for Virginia.
On August 1, Winnay met the Salem Red Sox in Lynchburg, Virginia, to play the Lynchburg Hillcats, affiliate of the Cleveland Guardians. He debuted the next day, reaching base in all four of his plate appearances and playing third base. Listed at 6-foot-3, 220-pounds, the right-handed batter and thrower will develop at first base, third base, and left field.
Winnay is an only child. His parents both work full-time jobs and plan to see him play in Salem soon.
“He’s loved it,” his mother said. “He loves the teammates and coaches he met, and he’s super happy with the development guidance he’s getting.”
Winnay, who said attended more than 100 Red Sox games growing up, including the 2018 World Series, has two more semesters’ worth of credits to complete his undergraduate degree in communications. He plans to chip away at it part-time. Weighing the pros and cons of signing with the Red Sox vs. returning to Wake Forest for his last season of college eligibility is “the toughest decision” he’s had to make, but one he and the organization both feel good about.
“We’ve known him for a long time, and I think he was a guy that even last year we had some draft interest in,” Red Sox Director of Amateur Scouting Devin Pearson said, via The Athletic. “Just being able to get him this year, when we did, we’re super excited.”
Winnay, a Newton resident since he was 2, attended Newton Public Schools through sixth grade before transferring to Belmont Hill for grades 7-12. His parents still live in Newton.
Nick Wang played with Winnay together in Little League, and they have been friends since grade school. They even played against each other in college as rivals in the Atlantic Coast Conference.
Wang is in the midst of his own Division I baseball career at Boston College. A power hitting infielder for the Eagles, Wang began his career at Holy Cross, where he earned the Patriot League Rookie of the Year award. He’ll return to BC next spring after a medical redshirt this year. They trained together during off-seasons, sometimes hitting in a cage in Winnay’s back yard. Wang keeps in touch with Winnay and said his friend reported a good professional experience thus far.
“One of our goals was to play college baseball, and that was the focus growing up,” Wang said. “I knew by high school he’d eventually be a professional baseball player. It wasn’t a matter of if, it was when.”
Winnay played three years at Wake Forest, transforming from reserve to stand out. All 30 MLB teams scheduled a meeting with Winnay last fall after a strong sophomore season, which he continued as a junior, batting .296 with 15 home runs, 13 doubles, and 65 RBI across 50 games. He also raised his on-base percentage significantly by cutting down on strikeouts while keeping a similar walk rate.
The Red Sox liked what they saw and took him.
A whirlwind summer started in Winston-Salem, North Carolina on the campus of Wake Forest. Who knows where it might end?
“The first year is when people really buy in and take jumps,” Winnay said. “I really like everything they have to say offensively, so I’m going to buy into that and do what I’ve done the past couple years.”
