Before it ended with a trip to the injured list in late August, Red Sox infield prospect Jack Winnay was putting the finishing touches on a very strong first full season in pro ball.
Winnay entered 2026 unranked by Baseball America, MLB Pipeline, and SoxProspects.com after being selected by the Red Sox in the 13th round (388th overall) of the 2025 draft out of Wake Forest. After signing for $150,000, the Newton, Mass. native and Belmont Hill product made the most of his professional debut, hitting .321/.393/.434 with one home run and 11 RBIs in 15 games (61 plate appearances) for Low-A Salem.
As a result, Winnay broke camp with High-A Greenville this spring but initially struggled to adjust to the level. The 23-year-old got off to a slow start at the plate, managing just a .177/.380/.241 line with one home run and 10 RBIs through his first 24 games (108 plate appearances) for the Drive. He then seemingly turned a corner in early May and began hitting for more power, slashing .312/.476/.615 with 10 home runs and 21 RBIs over his next 32 games (143 plate appearances) before being promoted to Double-A Portland in late June.
At the time of the promotion, Winnay had batted .255/.434/.457 with five doubles, 11 home runs, 31 RBIs, 43 runs scored, 53 walks, and 51 strikeouts in 56 games (251 plate appearances) for Greenville. The right-handed hitter stayed hot upon moving up another level, producing a .313/.404/.495 line with four home runs and 11 RBIs in his first 28 games (114 plate appearances) for Portland through the end of July. He then cooled off a bit before landing on the 7-day injured list with a bruised right forearm on August 27.
Taking a cautious approach, the Red Sox ultimately elected to shut Winnday down for the final two weeks of Portland’s season. He ended up batting .268/.365/.439 with nine doubles, six home runs, 15 RBIs, 26 runs scored, 19 walks, and 36 strikeouts in 45 games (181 plate appearances) for the Sea Dogs down the stretch.
Overall, then, Winnay slashed .261/.405/.449 with 14 doubles, 17 home runs, 46 RBIs, 69 runs scored, 72 walks, and 87 strikeouts in 101 games (432 plate appearances) between Greenville and Portland this season. He posted a .247/.398/.397 line in 362 plate appearances against right-handed pitching and a .328/.443/.707 line in 70 plate appearances against left-handed pitching.
Among 21 Red Sox minor leaguers who, regardless of level, logged at least 400 plate appearances in 2026, Winnay ranked first in on-base percentage, second in walk rate (16.7%), third in OPS (.854), wOBA (.392), and wRC+ (127), fifth in batting average, sixth in swinging-strike rate (9.3%), seventh in slugging percentage, eighth in strikeout rate (20.1%), and ninth in isolated power (.188), per FanGraphs.
Defensively, Winnay saw the majority of his playing time between his stops in Greenville and Portland at the corner infield positions. The 6-foot-3, 220-pounder made 68 starts at third base, where he committed 15 errors in 147 chances, and 25 starts at first base, where he committed just one error in 216 chances. He also made four starts at DH.
After beginning the season unranked, Winnay is now regarded as Boston’s No. 21 prospect by Baseball America, No. 23 by MLB Pipeline, and No. 19 by SoxProspects.com. All three outlets highlight his advanced approach and good swing decisions at the plate, which Red Sox senior director of player development Brian Abraham touched on when speaking about Winnay in August.
“He sees a lot of pitches, has a really good understanding of strike zone, walks a lot, makes a lot of contact, does not strike out a lot, and impacts the baseball,” Abraham told MassLive.com’s Christopher Smith. “So usually those are recipes for success.”
Winnay has also worked to improve his bat speed since being drafted by the Red Sox. In 2026, he added “3-4 mph to his exit velocities,” which helped him pull “the ball more than he did in his first taste of pro ball” and get “more out of his solid raw power,” according to his MLB Pipeline scouting report.
Barring a trade or other move this winter, Winnay — who will not turn 24 until next June — is projected by SoxProspects.com to return to Portland out of the gate in 2027. That said, it would not be surprising to see him work his way up to Triple-A Worcester at some point after that.
(Picture of Jack Winnay: Olivia Faulkner/Minor League Baseball via Getty Images)
