The Boston Red Sox saw quite a few top prospects make their way to the majors last season, including the number one prospect in all of baseball, Roman Anthony. Despite the graduations of Anthony, Marcelo Mayer and Kristian Campbell, the team still boasts a farm system that is currently ranked near the middle of the league; with some breakouts this year, it could rise once more. Between players taking a leap from the 2025 season and new acquisitions from last year’s draft, there are many names worth monitoring heading into the season.
Let’s take a look at the first installment of TalkSox’s Top 20 prospects. These rankings were voted on by the writers.
No. 20: John Holobetz (Greenville Drive/Portland Seadogs)
Holobetz was the player to be named later in the Quinn Priester trade and immediately made an impact, beginning with High-A Greenville. Making 12 appearances there, Holobetz showcased an ability to keep walks limited as he allowed only 10 free passes in 63 innings of work. He also managed to strike out 62 batters in that same span. He would end up being promoted to Double-A Portland where he would finish the season, appearing in six games and tossing 37 2/3 innings to a 2.39 ERA. During that same span Holobetz looked even better, walking just five batters and allowing just one home run.
Holobetz starts on the first base side of the rubber and has a deceptive delivery, as he manages to hide the ball well. His repertoire is a fastball that can top out at 96 mph and has shown bat-missing ability and he’s comfortable using it at the top of the strike zone. He also has a slider that is his weakest pitch due to inconsistent feel. Entering spring training in 2026, he’s tweaked it to become more of a bullet slider.
The 23-year-old also has a curveball that he struggles to land in the strike zone consistently and a changeup that has some two-seamer action to it. Both pitches are viewed as being potentially average pitches with enough development.
Holobetz will begin 2026 back with Portland but should he do well to open the season and the Red Sox are forced to call up their starting pitching depth from Worcester, he could see a promotion to Triple-A by the middle of the season. Despite a decent fastball and an improved slider, Holobetz’s ceiling is likely that of a middle reliever unless he can develop a third reliable offering.
No. 19: Conrad Cason (Florida Complex League)
Cason was a highly touted prospect when drafted back in 2024 thanks in part to his potential as a two-way player. Coming out of high school, his fastball was already capable of hitting the high-90s, and in the field he showed an ability to be an athletic defender along with the potential to develop power at the plate as he continued to grow.
Unfortunately for Cason, his first experience playing professional baseball was mixed. While he managed to make appear in three games (one as a pitcher and two as a hitter), an injury shut him down for the season. On August 14, 2025, he underwent Tommy John surgery, which will cost him his 2026 season as a pitcher. His lone appearance as a pitcher was impressive, however, tossing two innings of hitless baseball and striking out five batters while walking just one.
Cason has been working out as a fielder since arriving at spring training, taking ground balls with other minor-league infielders at shortstop and tossing it across the diamond to first base. He’s stated that his arm feels good, and it seems like once he gets back into action, he’ll play either second base or shortstop to see how his arm is holding up.
From a pitching standpoint, he has a fastball that has topped out at 98 mph and is arguably his best pitch. He also has a breaking ball that is inconsistent as it can look like either a curveball or a slider depending on spin rate. His final pitch is a changeup that currently sits in the low-80s.
Offensively, he has quick hands and a solid understanding of the strike zone but needs to work on recognizing pitches. Has average power, though that should improve as he continues to grow physically and his speed is viewed as being above average. Defensively, he’s an athletic fielder that could easily move to center field thanks to his great arm.
Despite being a two-way player, he’s viewed as being better as a pitcher and should he struggle at the plate, the team could transition him full time to the mound. Due to his age and the lost experience in 2025, Cason will likely open the season in the Florida Complex League. Playing in his age-19 season, we’ll likely see him make it to Salem before the end of the season so long as he suffers no setbacks.
No. 18: Nelly Taylor (Greenville Drive)
Taylor, who was drafted in the 11th round of the 2023 draft, enters camp after playing in the Arizona Fall League over the offseason. Most of his value comes from his speed and defense, as his bat is currently his weakest aspect of his game.
Taylor got into 108 games with Greenville in 2025, where he managed to hit .216/.355/.349 with 24 doubles, three triples, seven home runs and 41 RBIs. He also managed to steal 29 bases and walked 81 times.
Offensively, he has a quick bat, but his swing can get long at times and can often miss pitches in the zone. He struggles against off-speed and breaking pitches but manages to see a lot of pitches per at-bat. Due to his struggles against left-handed pitching at the lower minor-league levels, he’s very likely to be a platoon bat at his best. His power is viewed as being potentially league average especially when he pulls the ball and against right-handed pitchers, but it will all be determined by how he develops as an overall hitter. His speed is a huge quality of his profile, and he has great baserunning instincts that allow him to put pressure on the defense when he’s on base.
Defensively, he has good instincts and above-average range in the outfield and is likely to stick in center field long term thanks to his athleticism while his arm is viewed as being above-average.
With the need to continue working on his offensive game, Taylor will likely begin the season in Greenville and could spend most of the season there dependent on his development at the plate. Should he be a league-average hitter with Greenville in 2026, he could see a promotion to Portland some time near the end of July or early August depending on how the trade deadline goes. There’s also the possibility that he puts everything together and the team promotes him earlier than that, though it’s less likely at this point in time.
No. 17: Tyler Uberstine (Portland Seadogs/Worcester Red Sox)
Uberstine is an interesting prospect based on his career path so far. Drafted in the 19th round of the 2021 draft, Uberstine would make 26 appearances for the organization across the Florida Complex League, Low-A Salem and High-A Greenville from 2021 to 2022 before missing all of the 2023 season after undergoing Tommy John surgery. He would also miss most of 2024, appearing in just three games and tossing 4 2/3 innings.
Despite that, Uberstine put together an excellent season in his first taste of Double-A and Triple-A in 2025 as a 26-year-old. After just six starts and 29 2/3 innings with Portland, Uberstine was promoted to Worcester where he was a constant in the ever-changing pitching staff. Making 19 appearances, Uberstine tossed 91 innings and struck out 102 batters while recording a 3.56 ERA.
In what may have been a surprise for many, Uberstine was added to the 40-man roster over the offseason following his performance in Triple-A. With Worcester, he had a 26.9% strikeout rate and walked batters at a 9.5% rate.
As a pitcher, Uberstine starts on the first base side of the rubber and does a good job of repeating his mechanics while hiding the ball well. His pitches include a fastball that tops out at 95 mph. His velocity is pretty much the same as it was prior to the surgery and the pitch has shown an ability to miss bats. It has some arm-side run.
He also has a sinker that has shown good sink down in the zone. His other pitches include a slider that sits in the mid-80s and should he manage to land it in the zone, it could be an average pitch. His changeup sits in the low to mid-80s that has shown drop. His cutter has been an effective pitch against lefties and a curveball that he has rarely thrown since 2024.
Uberstine will open the year in Triple-A while serving as an up-and-down arm for the Red Sox either in the rotation or bullpen depending on what the big-league team needs. Should his secondary pitches fail to become league average offerings, he could end up in the bullpen full time thanks to his fastball and cutter.
Rodriguez was one of the key pieces in the Quinn Priester trade back in April of 2025, and at 19-years-old was assigned to Greenville.
His season had its ups and downs offensively, as he went through hot streaks and cold streaks as shown by a May that saw him hit .155/.276/.262 with 21 strikeouts in 22 games after hitting .257/.409/.414 in April while split between the Red Sox and Brewers organizations.
Offensively, Rodriguez has average bat speed and a short, choppy swing while struggling with velocity up in the zone. Due to his swing, he can get underneath the ball and will make weak contact on fly balls. Despite that, he makes contact on pitches in the zone and will use all fields making his hit tool potentially average down the line.
His power is viewed as below-average as he produces below-average exit velocities and lacks loft in his swing to be able to tap into his raw power. He also is viewed as having average speed and is not a premier stolen base threat. He also lacks instincts on the basepaths to make up for his lack of top-end speed.
Defensively, he’s likely to end up in a corner outfield position due to inconsistent routes and subpar instincts while in center field. His range is considered average, and he is not a standout defender at any of the outfield positions.
Rodriguez currently profiles to be a solid upper-minors depth piece with the ceiling of a emergency major league outfielder due to the lack of a carrying tool. Should his hit tool develop — and with serious improvement defensively as a corner outfielder — he could be a fourth or fifth outfielder for a major-league team. Rodriguez’s starting location for 2026 could be a tossup between Portland or Greenville depending on his spring performance.
What stands out from the 16-20 in this list? Let us know your thoughts in the comments!
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