One look at High-A Greenville’s 25-35 record doesn’t tell the whole story. The affiliate of the Boston Red Sox is easily the most exciting team in the organization. They started the year with Anthony Eyanson and Juan Valera in the rotation. While they lost Eyanson to a promotion and Valera to an injury, Kyson Witherspoon and Marcus Phillips are still there.
The offense features heavy hitters such as Justin Gonzales, Enddy Azocar, Henry Godbout, Yoeilin Cespedes and many more promising bats. However, 2025 13th-round pick Jack Winnay is stealing the show.
The heavy focus of the Red Sox in the 2025 MLB Draft was pitching. Of the first 13 picks, 10 of them were pitchers before the Red Sox selected Winnay out of Wake Forest in the 13th round.
Winnay, a third baseman, looked good in a short stint in Single-A to end the 2025 season. It was enough to get a few people talking. There were plenty of players overshadowing him in the system, though.
That’s fine. It makes sense why the heavy-hitters in the system are taking the spotlight. Winnay needs to start popping up on radars, though.
Red Sox fans should pay attention to High-A prospect, 2025 Draft pick Jack Winnay
The 2026 season started slowly, you would think. Winnay entered May hitting .197 with just one home run. However, he boasted a .376 on-base percentage. The results weren’t there yet, but you could see the process and how it would clearly lead to success for Winnay down the line.
Boy, did it. In May, Winnay slashed .290/.490/.623 with two doubles and seven home runs. He was always the best at-bat in the lineup; now, he was the best at-bat getting the best results (outside of maybe Mason White).
As of June 15, the right-handed hitter is slashing .242/.433/.464 with four doubles and 11 home runs. He’s driven in 31 runs and scored 41. Winnay has walked (49) more times than he's fanned (47).
Winnay has played good defense at third base and even looked solid when thrown over at first, but it’s the combination of power and plate discipline that makes him so intriguing. That .490 OBP in May is up there with what you’d see from Ted Williams. And his .433 OBP would be right around the best in the majors right now.
Obviously, High-A is a completely different animal than the big leagues, but it shouldn’t diminish what Winnay is doing in his first full season of professional baseball. The 23-year-old is doing it without sacrificing his power. In fact, it’s feeding into the home runs.
How does he do it? He’s not really swinging. Winnay’s zone swing percentage is literally in the first percentile at just 51.7% (according to TJStats). Meanwhile, he’s only swinging on pitches out of the zone 22.6% of the time (79th percentile). You could argue that maybe he could stand to swing more, but his current strategy is clearly working.
He’s pulling the ball 48.2% of the time and rarely putting it on the ground (34.2%). Combine those with a patient approach and some good old-fashioned raw power, and Winnay is a prototypical corner infield prospect that the Boston Red Sox haven’t had much of in recent years.
Red Sox fans should be getting excited about the guy in High-A pushing for a promotion with a mid-.400s OBP and double-digit homers before summer’s even hit. Things could get “incredible” with Jack-Jack at the dish.
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