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 for Anthony, Marcelo Mayer and Kristian Campbell, the team still boasts a farm system that is currently ranked near the middle of the league but with some breakouts this year could rise once more. Between players taking a leap from the 2025 season and new acquisitions from last year’s draft there are some names to look at heading into the season.
Let’s take a look at the first installment of TalkSox’s Top 20 prospects as we dive into the prospects ranked 16-20 as voted on by the TalkSox 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 on the Red Sox minor league pitching depth as the team had him begin 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. His strikeouts did drop to just 27, however.
Holobetz starts on the first base side of the rubber and appears to have 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. Along with the fastball he has a slider that is his weakest pitch due to an inconsistent feel for it. Entering spring training in 2026 he’s tweaked it to become more of a bullet slider. A bullet slider is where the pitch is supposed to spin gyroscopically making it more difficult to pick up and finger pressure from the index-finger is key in creating movement.
Holobetz 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 below-average pitches.
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 before 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 average 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), that was all he managed to do get into before an injury shut him down for the season. On August 14, 2025, he underwent Tommy John surgery and 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.
From a pitching standpoint he has a fastball that has topped out at 98 mph and is arguably his best pitch. Along with it he also has a breaking ball that is inconsistent as it can look like either a curveball or a slider due to his need to find a feel for spin. 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 but it should increase as he continues to grow physically and his speed is viewed as being above average. Defensively he’s an athletic fielder that should he be unable to stick at shortstop or second base, could easily move to center field while also having a great arm.
Despite being a two-way player, he’s viewed as being better as a pitcher and should he struggle hitting the team could transition him full time as a pitcher once his arm has fully recovered from the surgery. Due to his age and the lost experience in 2025, Cason will likely open the season in the Florida Complex League, and the team will likely take it slow with him. 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. Taylor very much has most of his value thanks to 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 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. Despite that, he doesn’t make the best throws all the time, but when he does the ball will move fast.
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 in June of 2023. 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 consistent in the ever-changing pitching staff. Making 19 appearances, Uberstine tossed 91 innings and struck out 102 batters while having 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 team needs. Should his secondary pitches fail to become league average offerings he could end up in the bullpen full time due 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. Despite that, he makes contact on pitches in the zone and will use all fields making his hit tool potentially average should he make better contact.
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 at-best average speed and is not viewed as a stolen base threat. He also lacks instincts on the base path to make up for his speed.
Defensively he’s likely to end up in a corner outfield position due to inconsistent routes to the ball and not great instincts while in center field. His range is considered average and is not a standout defender at any of the outfield positions. He could end up being average as a defender in left field but is viewed as a below-average defender in center field. He also has average arm strength that plays best in left field.
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 improve 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 the team’s feelings towards him. If they want to get other players more reps in Greenville he could open in Portland as right now they could use a corner outfielder. If they think he isn’t ready for Double-A pitching he could start in Greenville but should he open the season well enough he could be moved up to Portland.
What stands out from the 16-20 in this list? Let us know your thoughts in the comments!