Inside The Red Sox

Which Red Sox Prospects Actually Matter in 2026

Here are the names to watch closely...
Sep 16, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Connelly Early (71) delivers a pitch during the first inning against the Athletics at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images
Sep 16, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Connelly Early (71) delivers a pitch during the first inning against the Athletics at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images | Paul Rutherford-Imagn Images

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The world of prospects can be confusing at times, so let's clear up the landscape a bit for Boston Red Sox fans.

Of all the exciting farmhands in the Boston Red Sox's system, there are a select few watching especially closely this year. Some will be on the big-league roster before you know it, while others might take a while longer to arrive, but could transform the outlook of the team someday.

We'll separate these prospects in terms of how soon they could contribute, plus how impactful their contributions could be. It will make sense once we start moving, so without further ado...

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Short-term, major impact: Connelly Early and Payton Tolle

Payton Tolle
Pitchers Payton Tolle (left) and Connelly Early (second from left) stand for the national anthem ahead of Triple-A Worcester's game at Polar Park on Aug. 21, 2025. | WooSox Photo/Ashley Green / USA TODAY NETWORK via Imagn Images

The Red Sox's two left-handers who debuted late last season are both technically still "prospects," as evidenced by the fact that they're likely to begin the year in Triple-A. It's not immediately clear when they'll get their chance to impact the rotation, but there always seem to be more starting pitching injuries than we expect at the start of a year.

It could go either way at this point as to which lefty becomes the more reliable starter. Tolle's ceiling is higher because of his unicorn fastball, but Early demonstrated more command, pitchability, and nerves last fall.

Short-term, smaller impact: Tyler Uberstine, Tyler Samaniego

Samaniego
Feb 17, 2026; Lee County, FL, USA; Boston Red Sox pitcher Tyler Samaniego (78) poses for a photo during media day at JetBlue Park. Mandatory Credit: Kim Klement Neitzel-Imagn Images | Kim Klement Neitzel-Imagn Images

Neither of these two Tylers is likely to become a household name, but they're almost big-league-ready, and if injuries strike at any point, they'll probably fill in to help the Red Sox out of a jam. They're more than welcome to prove they can be impact guys, but it shouldn't be the expectation.

Medium-term, major impact: Kyson Witherspoon, Marcus Phillips, Anthony Eyanson

Kyson Witherspoon
May 21, 2025; Hoover, AL, USA; Oklahoma pitcher Kyson Witherspoon (26) pitches against Georgia in the second round of the SEC Baseball Tournament at the Hoover Met. | Gary Cosby Jr. / USA TODAY NETWORK via Imagn Images

One of the righties the Red Sox took with a high draft pick last year is bound to fly through the minors this year, if not multiple. Even if none of them pull the full Payton Tolle and make their major league debuts in the same season as their minor-league debuts, they're set up well to be key contributors in 2027.

You could include lefty Jake Bennett, the prospect from the trade with the Washington Nationals, on this part of the list as well. Franklin Arias, a slick-fielding shortstop, fits in somewhere between medium and long-term.

Long-term, major potential: Justin Gonzales, Dorian Soto

These are the teenagers whose ceilings are limitless, but who we won't see in Boston for a while. Incredible tools, but too early to know how they'll adjust to the upper levels of the minors. For every Roman Anthony at this age, there's a handful of players who never advance past Double-A.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org