Red Sox 2025 Draft Review: Jack Winnay's Updated Scouting Profile One Year Later

While the Boston Red Sox have focused mainly on pitching when it comes to the draft over the past few years, Jack Winnay was a bat the team targeted later in the 2025 process due to his incredible power. That's an area of the game that the Red Sox are desperately in need of, meaning Winnay could be one of the answers should he manage to properly develop other areas of his game.

Jack Winnay’s Updated Red Sox Scouting Report

Winnay, who grew up in Newton, Massachusetts and attended Belmont Hill High School, would go on to play college baseball for Wake Forest where by his second season he became a regular starter. During the summer after his first year, the young infielder played in the Futures Collegiate Baseball League for the Vermont Lake Monsters. Following that, Winnay showed his immense power during his final two seasons with Wake Forest where he hit 31 doubles, 35 home runs and drove in 123 runs.

Entering the 2025 draft, Winnay was ranked the 384th prospect in the class thanks to a solid approach at the plate paired with good angles off the bat. Despite the power and ability to make contact, he wasn’t viewed as a top prospect due to the lack of a carrying tool, and his power was questioned due to playing in a hitter-friendly park in college. He measures 6-foot-3 and weighed 220 pounds while displaying a solid, physical frame that was already built out and lacked much growth remaining.

With the organization, Winnay began his professional career with the then Salem Red Sox as he appeared in 15 games in 2025 and hit .321/.393/.434 with three doubles, one home run and 11 RBIs. The sample size showed that he was ready for the next level of minor league baseball and in 2026 he opened the season with the Greenville Drive.

After an outstanding start to his season, Winnay was promoted to Double-A Portland after hitting .255/.434/.457 with five doubles, 11 home runs and 31 RBIs in 56 games split between first base and third base. Winnay’s performance in the month of May also earned him TalkSox’s Minor League Hitter of the Month after he slashed .290/.490/.623 with seven home runs and 14 RBIs to go along with 26 walks.

Hit Tool

Winnay has showcased an ability to make solid contact everywhere he’s played since the summer of 2023 he spent with Vermont. Starting with his hands high, Winnay goes into a leg lift followed by his swing. He has good plate coverage but likes to get extended and pull the baseball while taking advantage of his strong points as a hitter. He has solid contact skills and plus pitch recognition that allows him to have an elite understanding of the strike zone. His bat path through the zone is good and knows how to hit the baseball at the right angle. He has shown he’s comfortable hitting secondary offerings but there is some concern over how he may handle velocity in the upper levels of the minors. He is willing to work a count and take a walk over trying to force a hit. Like most sluggers, he'll also have his fair share of strikeouts.

Potential above-average hit tool: 55 grade on 20-80 scale

Power Tool

Winnay’s best tool is his power, especially in the raw strength department. So far in 2026, he’s been able to translate that raw power into in-game power, as he’s had several loud home runs for Greenville. His power is mostly to the pull side, as 10 of his 11 home runs with Greenville were either to left field or left-center, and the one that wasn’t was to straight away center field. Thanks to his ability to hit the baseball at the ideal launch angle, he’s able to drive the ball with authority.

Potential plus power tool: 60 grade on the 20-80 scale

Running Value

For Winnay, running is not a big part of his game. He can go first to third on the right kind of hit, but due to his below-average speed, don’t expect him to be taking the extra base or trying to steal with regularity. For his batted balls to end up as extra-base hits, he’ll either need to hit it over the fence or drive it deep into the gap.

Potential below-average run tool: 40 grade on the 20-80 scale

Fielding Ability

While in college, Winnay played first base and the outfield, though he was predominantly a first baseman in his final season at Wake Forest after mainly playing the outfield his sophomore season. While with Vermont for summer ball, he split his time at first base and third base. So far in his young career, the Red Sox have no intention of playing him in the outfield as he’s split his time between first base and third base, with him having appeared at the latter position 55 times this year. In those 42 games, he has committed 15 errors. At first base, he’s appeared in 18 games without making an error.

Potential fringe-average field tool: 45 grade on the 20-80 scale

Arm Strength

Winnay’s arm is viewed as average. It’s strong enough to handle third base, but it won't make or break his defensive profile.

Potential average arm tool: 50 grade on the 20-80 scale

Outlook with Red Sox

With the lack of in-game power on the major-league roster, Winnay will be given chances to develop into a potential major-league bat. Right now, Winnay’s ceiling looks to be that of a bench bat, but that could change should his hit tool develop as predicted. Due to the lack of speed in his game and his questionable ability to currently remain at third base long-term, Winnay’s value will remain tied to his hitting. He has shown an advanced approach at the plate but as he moves through the minors, he'll need to prove he can handle the more advanced pitching, especially when it comes to velocity.

2026 Final Prediction

With Winnay’s promotion to Portland coming a little sooner than imagined, there is little room to dream on another quick promotion. The 13th-round pick will remain with Portland for the remainder of the season, getting at-bats against the toughest competition Double-A has to offer. He’ll also be playing at Portland’s Delta Dental Park, which isn’t as much of a hitter’s park as Fleur Field was, which will help to show if his first half of 2026 was thanks to ballpark factors. Expect Winnay to get plenty of time split between third base and first base as the organization looks to see him settle down defensively.  

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