How local Red Sox prospect Jack Winnay fared in first full pro season

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 left wrist contusion 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)

Red Sox promote Newton native, power-hitting prospect Jack Winnay to Double-A Portland

The Red Sox have promoted corner infield prospect Jack Winnay from High-A Greenville to Double-A Portland, as was first reported by Andrew Parker of SoxProspects.com.

Winnay, who turned 23 earlier this month, is in his first full professional season. The Newton, Mass. native (and Belmont Hill alumnus) was selected by the Red Sox in the 13th round (388th overall) of the 2025 draft out of Wake Forest. He received an at-slot $150,000 signing bonus and debuted at Low-A Salem last August, batting .321/.393/.434 with one home run and 11 RBIs in a limited 15-game sample.

After integrating himself with the Red Sox player development program over the winter, Winnay entered his first spring training with little fanfare and broke camp with Greenville as an unranked prospect. The right-handed hitter struggled out of the gate, slashing just .184/.382/.250 with one home run and nine RBIs in his first 23 games (102 plate appearances) for the Drive through May 3. From there, however, he began to turn a corner offensively — particularly in the power department — and hit .304/.470/.598 with 10 home runs and 23 RBIs across his next 33 games (149 plate appearances) before being promoted late Sunday.

Overall, Winnay batted a respectable .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 to begin the 2026 season. He posted a .364/.475/.788 clip in 40 plate appearances against lefties and a .232/.427/.387 clip in 211 plate appearances against righties.

Among the 80 qualified hitters in the hitter-friendly South Atlantic League, Winnay ranks second in walk rate (21.1%), fourth in on-base percentage, sixth in wOBA (.413), ninth in wRC+ (136), 12th in swinging-strike rate (8.9%), 14th in OPS (.891), 22nd in strikeout rate (20.3%), 27th in isolated power (.202), 28th in slugging percentage, and 35th in batting average, according to FanGraphs.

Defensively, Winnay primarily split his playing time with Greenville between the two corner infield positions. The 6-foot-3, 220-pounder made a team-leading 40 starts at third base, committing 12 errors in 94 chances, and 14 error-free starts at first base. He also made one start at DH and has prior experience in the outfield.

Thanks to his recent hot stretch at the plate, Winnay is now regarded as Boston’s No. 40 prospect by SoxProspects.com. He is not yet ranked by Baseball America or MLB Pipeline, but that may not be too far behind, given the amount of attention he has received as of late.

Winnay joins third-round right-hander Anthony Eyanson as the second member of the Red Sox’ 2025 draft class to reach the upper minors this season. As was the case for Eyanson — who has forged a 1.46 ERA through his first six Double-A starts (24 2/3 innings) — the jump to Portland represents a new challenge for Winnay in the form of more advanced competition.

The Sea Dogs hit the road and open a six-game series against the Hartford Yard Goats on Tuesday night.

(Picture of Jack Winnay: Gwinn Davis/Greenville Drive)