{"id":2848,"date":"2026-06-16T12:05:19","date_gmt":"2026-06-16T12:05:19","guid":{"rendered":"https:\/\/bostonrelocationinsider.com\/?p=2848"},"modified":"2026-06-16T12:05:19","modified_gmt":"2026-06-16T12:05:19","slug":"newton-native-jack-winnay-is-living-his-dream-in-the-red-sox-system-and-developing-as-a-power-hitter-as-well","status":"publish","type":"post","link":"https:\/\/bostonrelocationinsider.com\/?p=2848","title":{"rendered":"Newton native Jack Winnay is living his dream in the Red Sox system, and developing as a power hitter as well"},"content":{"rendered":"<article>\n<div>\n<p><span>It\u2019s 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.<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=2846\">More than half of Massachusetts voters say they\u2019ve weighed leaving the state, new Suffolk\/Globe poll finds<\/a><\/p>\n<p><span>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.<\/span><\/p>\n<p><span>\u201cIt 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,\u201d said Winnay, 23. \u201cBut 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.\u201d<\/span><\/p>\n<\/div>\n<div>\n<div>\n<div>\n<div><span>Get Starting Point<\/span><\/div>\n<div><span>A guide through the most important stories of the morning, delivered Monday through Friday.<\/span><\/div>\n<div>\n<div><label>Enter Email<\/label><\/p>\n<div><button>Sign Up<\/button><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<p><span>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. <\/span><\/p>\n<p><span>\u201cIt just felt like the stars aligned,\u201d said Winnay. \u201cIt was this perfect day, and obviously my parents were ecstatic and super excited for me. It was just such a surreal moment.\u201d<\/span><\/p>\n<div><span>Related<span>: <\/span><\/span>What exactly is ailing Roman Anthony? And when might he be back with the Red Sox?<\/div>\n<p><span>Of course, it\u2019s 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.<\/span><\/p>\n<p><span>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 \u2014 a first baseman\/outfielder in college who has been playing first and third in pro ball \u2014 has been putting up big numbers in High-A Greenville for the last six weeks.<\/span><\/p>\n<p><span>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\u2019s repeatedly shown the ability to pull the ball in the air and take advantage of the favorable hitting conditions in the South Atlantic League \u2014 and particularly at his home ballpark of Fluor Field, which features a modified version of the Green Monster in left.<\/span><\/p>\n<div><\/div>\n<p><span>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.<\/span><\/p>\n<p><span>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\u2019s in-game production has blossomed thanks to his ability to make solid contact in the air to left field.<\/span><\/p>\n<p><span>\u201cI definitely do [pull the ball in the air] intentionally,\u201d said Winnay. \u201cIn 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\u2019s your superpower, there\u2019s no point in taking it away. You should use it as much as possible, so I do.\u201d<\/span><\/p>\n<p><span>Winnay doesn\u2019t do so recklessly. Early in counts, he looks for specific pitches he can pull in the air. If he doesn\u2019t see them, he\u2019s 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 \u2014 particularly against lefties, whom the 6-foot-3-inch righthanded hitter is pulverizing at a .364\/.475\/.788 clip.<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=2844\">Explore the full results of the Suffolk University\/Boston Globe poll of Massachusetts voters<\/a><\/p>\n<p><span>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.<\/span><\/p>\n<p><span>The progress Winnay has made so far \u2014 both in terms of bat speed, and his re-education at third base \u2014 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.<\/span><\/p>\n<p><span>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.<\/span><\/p>\n<p><span>\u201cIt\u2019s definitely surreal, especially now in Greenville with the Green Monster out there, and the way they play \u2018Sweet Caroline\u2019 in the eighth inning. It really feels like there\u2019s a real path to Fenway, and like I\u2019m playing in front of a Boston fan base,\u201d said Winnay. \u201cIt feels super special putting that jersey on every day. I am truly grateful.\u201d<\/span><\/p>\n<div>\n<h2>Three up<\/h2>\n<\/div>\n<p><span>\u22c5 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\u2019s in the conversation as a top-five prospect in the system.<\/span><\/p>\n<p><span>\u22c5 Catcher Franklin Primera, 18, is having a standout season in the Florida Complex League, hitting .447\/.587\/.750 with six homers \u2014 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.<\/span><\/p>\n<div><span>Related<span>: <\/span><\/span>As it turns out, not only can the Red Sox\u2019 Wilyer Abreu hit lefthanders, he can do damage against them<\/div>\n<p><span>\u22c5 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 45\u2153 innings, with a delivery and arm angles that suggest interesting room to develop.<\/span><\/p>\n<div>\n<h2>Three down<\/h2>\n<\/div>\n<p><span>\u22c5 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 2\u2153 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\u2019ll 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.<\/span><\/p>\n<p><span>\u22c5 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.<\/span><\/p>\n<p><span>\u22c5 Shortstop Hector Ramos, 18, a multi-dimensional talent, hasn\u2019t played in the FCL since May 26 due to a right elbow strain. In 12 games, he\u2019s hitting .190\/.308\/.262.<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=2842\">Many voters can\u2019t name a signature achievement for Healey, Suffolk\/Globe poll finds. It may not matter in November.<\/a><\/p>\n<\/div>\n<\/article>\n","protected":false},"excerpt":{"rendered":"<p>Winnay, who played high school baseball at Belmont Hill, has 11 home runs in 51 games for High-A Greenville this season.<\/p>\n","protected":false},"author":1,"featured_media":2847,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[7],"tags":[],"class_list":["post-2848","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-sport"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.6 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Newton native Jack Winnay is living his dream in the Red Sox system, and developing as a power hitter as well - Boston Relocation Insider<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/bostonrelocationinsider.com\/?p=2848\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Newton native Jack Winnay is living his dream in the Red Sox system, and developing as a power hitter as well - 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