Red Sox Major Pipeline: Prospect Updates and Movement Toward the Majors

The Boston Red Sox have a lot to be excited about down in the minor leagues right now.

Boston had a few down years, but the club took a step in the right direction in 2025 as its prospects started to make the jump to the big leagues, including Roman Anthony, Marcelo Mayer and Connelly Early, among others.

The Red Sox's big league roster is full of former prospects who have now become consistent contributors in the major leagues. Despite all of the guys making the jump to the majors, like Anthony and Mayer, and others traded away, like Jhostynxon Garcia and Brandon Clarke, Boston still has one of the better farm systems in the game and it's loaded with guys who could impact the club at the big league level in 2026.

With that being said, let's take a look at three of Boston's top prospects right now.

Payton Tolle, Left-Handed Pitcher — No. 1 Prospect

Feb 26, 2026; Fort Myers, Florida, USA; Boston Red Sox pitcher Payton Tolle (70) throws a pitch in the sixth inning against the Tampa Bay Rays at JetBlue Park at Fenway South. Mandatory Credit: Jim Rassol-Imagn Images | Jim Rassol-Imagn Images

Current Level: Triple-A Worcester

How is Payton Tolle playing so far in 2026? Tolle competed for the final spot in the Red Sox's starting rotation, but missed out. Early made the rotation out of camp and Johan Oviedo was put in the bullpen. Tolle is down in Triple-A, continuing to be stretched out as a starter. Tolle has made one start so far and struggled. He pitched four innings and allowed four earned runs and six runs total. On the bright side, he struck out six batters over that stretch.

Tolle made four appearances for Boston in Spring Training and had a 2.53 ERA across 10 2/3 innings pitched. The first start of the season didn't go well for Tolle down in Triple-A, but there are plenty more to come. His performance in Spring Training was enough to be excited.

When could Tolle get called up? Mid-2026

Jake Bennett, Left-Handed Pitcher — No. 7 Prospect

Mar 3, 2026; Lee County, FL, USA; Boston Red Sox pitcher Jake Bennett (64) pitches in the first inning against the Puerto Rico. Mandatory Credit: Jim Rassol-Imagn Images | Jim Rassol-Imagn Images

Current Level: Triple-A Worcester

How is Jake Bennett playing so far in 2026? Like Tolle, Bennett was someone who made some waves in Spring Training. He joined the organization this past offseason in an intriguing trade with the Washington Nationals. He has made one start down in Triple-A so far for Worcester and thrived. The big lefty pitched three innings and struck out five batters and didn't walk anyone. There is so much starting pitching in the system right now that the pathway isn't great for Bennett right now to the big leagues in the rotation, but he certainly would be an intriguing relief option later on.

When could Bennett get called up? Mid-2026

Mikey Romero, Infielder — No. 13 Prospect

Mar 18, 2026; Tampa, Florida, USA; Boston Red Sox second baseman Mikey Romero (72) doubles against the New York Yankees in the seventh inning during spring training at George M. Steinbrenner Field. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | Nathan Ray Seebeck-Imagn Images

Current Level: Triple-A Worcester

How is Mikey Romero playing so far in 2026? There was a point in Spring Training when Romero was a "dark horse" to make the big league roster. He didn't make the job out of camp, but is down in Triple-A. So far this season, he has slashed .273/.308/.636 in three games with one homer and four RBIs. Right now, it would likely take an injury for Romero to make the jump to the next level.

When could Romero get called up? Late-2026