The Boston Red Sox have been surprisingly stingy with prospect promotions this season. Last year, it felt like prospects were flying through the system, and we were getting news of promotions every other week.
However, this year, we’ve seen multiple players staying at levels they’ve conquered far longer than feels necessary. Therefore, it was welcome news when Andrew Parker of SoxProspects reported that the Red Sox were promoting a High-A prospect who had long deserved to move up to Double-A. That prospect is third baseman Jack Winnay.
The right-handed hitter slashed .255/.434/.457 with five doubles and 11 home runs in 56 games in High-A. He drove in 31 runs and scored 43. Winnay had a ridiculous 21.1% walk rate with a lower 20.3% strikeout rate.
Red Sox promote 2025 13th-round MLB Draft pick Jack Winnay to Double-A
The Red Sox are promoting Jack Winnay to Double-A Portland, i’m told.
— Andrew Parker (@ByAndrewParker) June 21, 2026
Winnay, their 13th round pick last year out of Wake Forest, has hit 11 HRs over 55 games for Greenville this year.
He’s also a former Belmont Hill grad in Massachusetts.
The 23-year-old was hitting just .177 entering May 6, but has flipped a switch since then and clearly found a rhythm. It’s important to note that even when at that low, Winnay still had an OPS of .380.Â
The Wake Forest product has shown incredible patience at the plate, you could even argue to a fault. According to TJStats, he swings at 22.1% of pitches out of the zone (83rd percentile). That’s fantastic. Meanwhile, he only swings at 54% of pitches in the zone (3rd percentile).
It’s clearly worked well for Winnay so far. He’s drawing a ton of walks and working favorable counts. Those favorable counts have led to plenty of bombs.
Winnay’s patient approach will be tested more in Double-A. The pitching is much more advanced, and he will likely find himself battling back in unfavorable counts more often than he did in High-A. Therefore, he might need to make some adjustments while with Portland.
However, that’s what the minor leagues are for. There's no doubt Winnay has the talent to acclimate. He has an elite eye and phenomenal power. That combination can take him far, especially if he keeps making small adjustments. Boston found a legitimate prospect late in the 2025 MLB Draft, and he’s rewarded them so far.
The Red Sox farm system is pretty loaded. That being said, they could absolutely benefit from a surge in corner infield prospects and power-hitting prospects. Winnay fits both of those molds. Brooks Brannon and Justin Gonzales (kind of) are both able to play first base, but Mikey Romero has been the only real third base prospect in the upper levels of the minor leagues. Winnay adds something real to that mix.
Add us as a preferred source on Google