Newton native Jack Winnay is living his dream in the Red Sox system, and developing as a power hitter as well
It’s been a long time since the Red Sox had the most homegrown of homegrown players: A Massachusetts native who was drafted by the team and rose through their farm system to forge a path to Boston. Jack Winnay is hoping to rectify that.
Winnay, a Newton native who attended Belmont Hill before heading to Wake Forest for college, emerged as a middle-of-the-order producer at Wake. He pounded 20 homers as a sophomore and 15 more as a junior. But as the 2025 draft approached, coming off a junior campaign he considered a disappointment, Winnay was only interested in leaving college under a very specific condition.
“It got to the point with my agent where we decided it was either the Red Sox or going back to school, just because I loved Wake,” said Winnay, 23. “But I genuinely, from the bottom of my heart, believed in the Red Sox player development system, and I thought that they would get the best version of me as a hitter, just with what they teach. And then obviously being the hometown kid, that was always just a dream of mine to put on that jersey.”
The Sox made the dream a reality. They took him in the 13th round of the 2025 draft and signed him for a $150,000 bonus.
“It just felt like the stars aligned,” said Winnay. “It was this perfect day, and obviously my parents were ecstatic and super excited for me. It was just such a surreal moment.”
Of course, it’s one thing to be drafted by the Sox and quite another to advance through their system. The last Massachusetts native to get drafted by the Sox and advance through the farm system before wearing the big league uniform of his hometown team was outfielder Alex Hassan, a 2009 draftee out of Duke who enjoyed a brief callup in 2014.
But Winnay is taking early steps in an effort to forge that rare path. After a slow start through the first five weeks of his first full pro season, the 23-year-old — a first baseman/outfielder in college who has been playing first and third in pro ball — has been putting up big numbers in High-A Greenville for the last six weeks.
In 27 games from May 7 through June 14, Winnay hit .318/.487/.682 with 10 homers and more walks (27) than strikeouts (26). As a righthanded hitter, he’s repeatedly shown the ability to pull the ball in the air and take advantage of the favorable hitting conditions in the South Atlantic League — and particularly at his home ballpark of Fluor Field, which features a modified version of the Green Monster in left.
Winnay features what evaluators consider roughly average raw power, and said that his primary offensive goal is to increase his bat speed in order to boost that trait. Since he signed with the Sox, Winnay said his average bat speed has gone from 69 m.p.h. in 2025 to 71 now.
That bat speed is still a tick shy of the big league average of 72, but certainly at a level up to big league standards, particularly given Winnay’s in-game production has blossomed thanks to his ability to make solid contact in the air to left field.
“I definitely do [pull the ball in the air] intentionally,” said Winnay. “In college and even high school, that was always the strongest part of my game, being able to pull the ball in the air and hit home runs. If that’s your superpower, there’s no point in taking it away. You should use it as much as possible, so I do.”
Winnay doesn’t do so recklessly. Early in counts, he looks for specific pitches he can pull in the air. If he doesn’t see them, he’s content to work deeper into counts and, with two strikes, go with a pitch to all parts of the field or take a walk. As a result, he owns a 21-percent walk rate and a strong overall performance — particularly against lefties, whom the 6-foot-3-inch righthanded hitter is pulverizing at a .364/.475/.788 clip.
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Already, Winnay has had a number of pinch-me moments in the organization, including sightings of David Ortiz and Pedro Martinez in Red Sox camp this spring. But the goal is not merely to experience that transition as a minor leaguer, but to do the work needed to advance to Boston.
The progress Winnay has made so far — both in terms of bat speed, and his re-education at third base — as well as working out with fellow Bay State natives who have reached the big leagues, including fellow Wake Forest alums like Shane Smith and Jared Shuster, has created a sense of possibility.
A player whose passion for the game was inspired by regular trips to Fenway Park is increasingly able to dream of stepping onto the field in Boston as a Red Sox player.
“It’s definitely surreal, especially now in Greenville with the Green Monster out there, and the way they play ‘Sweet Caroline’ in the eighth inning. It really feels like there’s a real path to Fenway, and like I’m playing in front of a Boston fan base,” said Winnay. “It feels super special putting that jersey on every day. I am truly grateful.”
Three up
⋅ Outfielder Enddy Azocar, 19, is off to a brilliant start since his promotion to High-A Greenville, hitting .344/.385/.574 with two homers and eight extra-base hits through 14 games. As a potential well-rounded impact player, he’s in the conversation as a top-five prospect in the system.
⋅ Catcher Franklin Primera, 18, is having a standout season in the Florida Complex League, hitting .447/.587/.750 with six homers — numbers that reflect a player hitting the ball hard in the air, controlling the zone (20 percent walk rate) and not whiffing (10 percent strikeout rate), while also showing solid defensive tools behind the plate.
⋅ Lefthander Dylan Brown, who was taken out of Old Dominion in the eighth round last year, has had an intriguing, below-the-radar pro debut. The 6-5, 21-year-old, who tops out around 95 m.p.h., has a 32 percent strikeout rate in 45⅓ innings, with a delivery and arm angles that suggest interesting room to develop.
Three down
⋅ While righthander Anthony Eyanson has a sparking 1.74 ERA in five starts with Double-A Portland, his control since his promotion from Greenville has been spotty. He walked a season-high five in just 2⅓ innings in his last start, and has a 15 percent walk rate (against a 28 percent strikeout rate) with the Sea Dogs. Normal fatigue for a pitcher in his first full pro season is a logical reason (his four-seamer is sitting at 92-93 this month, and he’ll likely be skipped for a turn in the rotation soon), as well as efforts to add a cutter, and perhaps being too fine against more advanced competition.
⋅ Outfielder Justin Gonzales has experienced a downturn over the last four weeks, hitting .149/.208/.194 with one extra-base hit and just four walks in his last 16 games. For the season, the massive 19-year-old is still posting a solid .264/.349/.423 mark with seven homers in High-A Greenville.
⋅ Shortstop Hector Ramos, 18, a multi-dimensional talent, hasn’t played in the FCL since May 26 due to a right elbow strain. In 12 games, he’s hitting .190/.308/.262.
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