One Red Sox Prospect From Each Affiliate Who Will Break Out In 2027

[Ben Lofy]

Even after the trades of Anthony Eyanson, Kyson Witherspoon, Enddy Azocar, and Harold Rivas, the Boston Red Sox's farm system has some high-end prospects. Franklin Arias, Justin Gonzales, and Franklin Primera are the organization's best, but there are some more under-the-radar candidates that could be primed for a breakout season in 2027.

So, let's pick one player from each level of the system who should skyrocket up prospect rankings next year.

Triple-A Worcester Red Sox: Gage Ziehl

Garrett Whitlock, Caleb Durbin, and Greg Weissert. At one point in their careers, all three of these players were in the New York Yankees' system. Now, all three have turned into big-time contributors for the Red Sox. The next former Yankee to find success with the Red Sox could very well be Gage Ziehl. 

Ziehl was drafted by New York in 2024 before being moved to the Chicago White Sox for Austin Slater a year later. The following offseason, the Red Sox acquired him in the Jordan Hicks deal. 

Ziehl started the 2026 season in Portland, earning a promotion to Worcester with a month left in the season. His 4.33 ERA in 17 starts with the Sea Dogs is nothing to write home about, but his underlying metrics tell a slightly different story. In his Double-A stint, his xFIP was 3.56, compared to a FIP of 4.17. 

His stats with Worcester are similar. His 4.02 xFIP over eight starts is 49 points lower than the actual results, suggesting that Ziehl is due for some positive regression in the near future. He has a regular five-pitch arsenal, relying on his cutter and sweeper the most. He does a good job pounding the zone, but his velocity will need work if he wants to reach a higher ceiling. His fastball sat at just 91-94 mph and while he can generate whiffs, he's certainly not elite in that regard.

Luckily for him, he’s in the right place. With recent success stories like Payton Tolle, Connelly Early, and Jake Bennett, the Red Sox pitching team has a track record of success with young pitchers. Ziehl is still only 23 years old, and with another year of development in the organization, he can emerge as valuable pitching depth.

Double-A Portland Sea Dogs: Jack Winnay

When you think of the Red Sox Double-A prospects, Jack Winnay doesn’t immediately jump out. But he should. 

The 2025 13th-round draftee out of Wake Forest struggled in High-A to start his first full professional season, but found his stride and made a successful jump up to Double-A later in the season. 

He has above-average raw power, exemplified by his 35 home runs in his final two seasons at Wake Forest, but he struggled to display it during his first season with Low-A Salem. But in 2026, he added 3-4 mph to his exit velocities and started to showcase his pop.

Winnay hit just .197 through the month of April, but he shook off the rough start. He earned a call-up to Portland by mid-June after compiling 11 home runs and a .891 OPS through 56 games. 

In addition, his plate discipline is excellent. He makes good swing decisions and isn’t afraid to take. He drew 53 walks in 188 at-bats in High-A. Comparatively, he struck out 51 times in the same stretch. 

The jump to Double-A was well-deserved, and Winnay hardly missed a beat. In 45 games, he hit .268 with a .804 OPS. His walk rate suffered slightly, but that’s to be expected with better pitching. He hit five fewer home runs than he did in High-A but also struck out less. 

With a full season facing better pitching and more time to fully unlock his raw power, Winnay projects as one of the Red Sox's most underrated hitting prospects heading into the offseason.

High-A Greenville Drive: Antonio Anderson

The Red Sox's third-round draft pick in 2023, Anderson was written off after two disastrous seasons to start his professional career. But Anderson didn’t write back. 

He hit .186 in 108 games in his first full season with Low-A Salem, compiling a measly .581 OPS from both sides of the plate. His 2025 campaign marked some improvements, as he hit .345 in 22 games with Salem before earning a call-up to Greenville. Then he came back down to earth, hitting .212 with the Drive. His OPS tumbled accordingly, from .924 to .569. 

But heading into 2026, Anderson made some adjustments. He simplified his swing, and the results were resounding. 

“Just having more of a simple swing, not doing too much with my hands and lower half—straight back, straight to the ball,” Anderson told MLB.com. 

He set career highs across the stat sheet, hitting nine homers, driving in 46 runs, and tallying 131 bases. Additionally, he led the Red Sox organization in opposite-field rate going the other way 35% of the time. His .826 OPS and .273 average were career highs, and he finally began to showcase the skills that made him a coveted draft prospect.

His career-best season has translated into a torrid start in the Arizona Fall League as well. In 13 games, Anderson is hitting .333 and has drawn 12 walks. He also has htree two home runs, including a 115.2-mph grand slam.

While Anderson’s 2026 campaign could be considered a breakout, he’s got more in the tank and will be a fun player to watch in 2027.

Low-A Salem RidgeYaks: Kleyver Salazar

Kleyver Salazar isn’t as well known as Salem’s other catcher, Franklin Primera, but he is one of the most intriguing players at the Low-A level in his own right. 

Signed out of Venezuela in 2023, Salazar’s first season with Salem wasn’t outstanding; in fact, it wasn’t even good. Four home runs and a .215 batting average are discouraging, and a 20.3% strikeout rate alongside a .603 OPS are just cherries on top. 

The expectations for Salazar’s second season were low, but he went above and beyond. He improved across the board, tripling his home run total with 12 and hitting .293. His OPS jumped to .882, and he cut his K% to 16.5% while drawing 60 walks. His underlying metrics further support the improvements; his BABIP jumped from .269 to .328, and his isolated power metric improved from .061 to .186.

His defense is also rock-solid. He has a strong arm and displays good movement behind the dish. 

While Primera is one of the Red Sox’s most-hyped prospects and will get preferential treatment behind the plate, Salazar shouldn’t slip through the cracks. If he can keep his momentum into 2027, or even improve on it, a call-up to High-A Greenville isn’t too far away.

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