Before every game of Jack Winnay’s Belmont Hill baseball career, he and a friend went to Comella’s for a chicken parm.
The Italian classic fueled a tremendous high school baseball career, one in which Winnay envisioned someday playing for the Boston Red Sox. That dream became a little more realistic last week, when the Red Sox selected the 22-year-old Winnay in the 13th round (388th overall) in the Major League Baseball draft. Winnay played his college ball at Wake Forest University.
“I honestly think that continuing to be a fan will be the best thing for me because it’s motivation to get to Fenway,” Winnay said. “I’ve always wanted to just play in the major leagues, and to be able to have a chance to do it for the Red Sox is even more motivation.”
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Though he’s a Newton native, Winnay spent plenty of time in Belmont — grades 7 through 12 at Belmont Hill. A four-year varsity starter for the Sextants, Winnay capped his high school career with 2022 Independent School League Hitter of the Year honors while leading Belmont Hill to a league title.
The rules governing the Major League Baseball draft are a bit complicated. A player can be selected from their high school team. If they choose not to sign a contract and instead go off to college, they have to wait until they have either completed a year of junior college or their junior year at a four-year NCAA program.
Michael Grant, who holds numerous roles, including assistant head of school at Belmont Hill, coached Winnay’s Sextant baseball teams. He described Winnay as “awesome” in high school with “a special gift to be extraordinarily confident without being cocky.” Winnay flashed an uncanny understanding of his own swing.
“We were a good team but we didn’t have the deepest of lineups, so nobody pitched to him,” Grant said. “With runners on base, he’d just go up and see six balls in the dirt. You could see long-term why professional scouts would be interested because he’s huge and has athletic tools that are different than others.”
Undrafted out of high school, Winnay blossomed from little-used freshman reserve to a feared power threat in the vaunted Atlantic Coast Conference. After spending the summer between his freshman and sophomore years with the Vermont Lake Monsters of the Futures Collegiate Baseball League (FCBL), the 6-foot-3, 220-pound right-handed batter and thrower flourished the next two seasons as part of the Demon Deacons’ regular starting nine. Winnay, who played the corner infield and outfield positions, belted 34 home runs with 104 RBIs over 119 games in two seasons as a starter.
“I think I just needed to grow, not only physically but as a person,” said Winnay, who credited extra hitting sessions with former Wake Forest assistant and current Duke hitting coach Matt Wessinger as a catalyst for his growth. “I wasn’t one of those freshmen who came in and expected to play… I knew it was going to be a little bit of a waiting game.”
By choosing to sign with the Red Sox, Winnay gave up his last year of NCAA eligibility, a common move for drafted college juniors. He had meetings with all 30 MLB teams in the fall, and felt strongly that five teams zeroed in on him. He learned of his selection on July 14, the second day of the 20-round draft, and signed a few days later for $150,000.
Red Sox Director of Amateur Scouting Devin Pearson told The Athletic the team will develop him at first base, third base, and left field.
“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,” Pearson said. “Just being able to get him this year, when we did, we’re super excited.”
Winnay, who estimates he has attended more than 100 Red Sox games, including the 2018 World Series, has two more semesters’ worth of credits to complete his undergraduate degree in communications. It’ll get completed over time. Weighing the pros and cons of signing with the Red Sox vs. returning to Wake Forest as “the toughest decision” he’s had to make.
“I loved my experience at Wake Forest so much,” Winnay said, “but at the end of the day, my dream was always to play in the major leagues.”
Winnay reported to the Red Sox spring training facility in Fort Myers, Florida, last Tuesday for physical testing. Normal baseball activities began this week, and it’s likely Winnay will report to a minor league affiliate before the end of the summer.
“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.”
