It’s officially Major League Baseball Draft week, with the draft just five days away, in the middle of All-Star Weekend. Of course, not every prospect can become the next Aaron Judge or Bryce Harper. That was covered last week in the “biggest missed opportunities of the decade” segment. There have been picks, however, where the players either were a success or were on track to be a success. These are Boston’s biggest hits in the draft since 2020.
One quick note: for the misses list, there was a criterion that they had to be a major league player, as prospects are hard to judge whether they are a missed pick or a huge pick. For the sake of one inclusion, this rule is tossed aside. It will primarily consist of major league players, though.
Biggest Red Sox Draft “Hits” Since 2020
Anthony Eyanson
Let’s get the minor leaguer out of the way first. Anthony Eyanson was a huge steal when drafted by the Red Sox, as the right-hander who was projected in the late first round fell to the middle of the third. While this was a surprise for the LSU star, and there was an apparent issue with his fastball that caused this slide, Boston saw his potential. And boy, has this decision paid off so far.
The number two prospect in the system (55 in baseball), and a Futures Game participant this year, has dominated the minor leagues in his first season. He started in High-A Greenville, along with a stacked rotation involving fellow 2025 draftees Kyson Witherspoon and Marcus Phillips, and stood out above them with a 0.44 ERA and a K/BB ratio of 11.33 (34 strikeouts to three walks). He’s done pretty well at the next level in Portland as well, with a record of 3-0 and a 1.74 ERA.
7 strikeouts over 5 innings of work for Anthony Eyanson on Saturday. pic.twitter.com/XR67dLDA1f
— Red Sox Player Development (@RedSoxPlayerDev) July 6, 2026
His mix of pitches is very interesting; as mentioned, during the pre-draft process, his fastball was seen as his weakest. Currently, he’s hitting triple digits in the strike zone too, helping him strike out roughly 35%(!) of the batters he’s faced. He’s working a mid-80’s slider, along with a mid-80’s splitter that’s starting to come to form. Based on his dominance and his improvement on his pitches, it’s safe to say this was a steal for Boston.
Chase Meidroth
Now this one’s a slightly weird situation as, along with Kyle Teel, they were successful minor league players in the Red Sox organization, but were traded prior to making their major league debuts. However, seeing as he’s probably the best player from the fourth round in 2022 (Troy Melton makes a good case), there’s a place for him on this list. Chase Meidroth was a middle infielder who performed well in Worcester in 2024, hitting .293 with an incredible 105 walks, contributing to a .437 OBP.
After Meidroth was shipped off to the Chicago White Sox in the Garrett Crochet blockbuster, it didn’t take him long to get called up to the big leagues. Called up in April of 2025 (coincidentally making his debut against the Red Sox), he had a decent rookie season, hitting .253 with five homers and 23 RBIs. This season however, he’s improved and become one of Chicago’s most important players this season. He may not have played with the Red Sox at the major league level, but he has certainly been a successful pick.
Roman Anthony
Roman Anthony has been a tricky name around Boston this year. Drafted in the third round of the 2022 draft, he quickly rose to eventually being the number one prospect in all of baseball. It came to a point where, after hitting a near 500-foot grand slam in Triple-A, people claimed him to be the next face of baseball. That was a tremendous amount of pressure to put on someone who hadn’t even cracked the majors yet.
And oddly enough, he had a great rookie season in 2025. While he didn’t manage to hit 20 homers or do anything that pops out, he had a .292 batting average and an OBP of .396. It also could be said that his call-up helped turn the season around. Before getting a season-ending injury to his oblique on September 2nd, 2025, the Red Sox went 46-27 since the June 9th call-up, the best in the American League that season during that roughly two-month stretch.
Of course, however, the discussions around Anthony have changed since his injury in early May, which went from a ten-day stint to a 60+ day IL stint. It’s really uncertain when this injury will heal and when he will come back. Surely, when he does, he’s not going to immediately be the player who received an eight-year, $130 million contract extension this past August. But if he can be serviceable, the team gets another depth piece in the lineup, with possibly a star for the future.
Payton Tolle and Connelly Early
Due to them being drafted in back-to-back years and debuting in a similar timeframe (with Payton Tolle being August 29th, 2025, and Connelly Early being September 9th, 2025), it makes more sense to put them together.
Tolle had been the Red Sox’s second-round choice in 2024, out of TCU. The big left-hander has quickly become a fan favorite here during his rise to the majors and after his call-up. His dominance comes from his fastball, which usually is in the upper 90s, although his best is 100.4 MPH. His curveball has been the most swing-and-miss pitch this season, though, with a whiff percentage of 45.7%.
His career moment so far was when he took a perfect game into the sixth inning against the New York Yankees. With how good he’s performed at a young age, mixed in with how much he’s beloved in Boston, Tolle’s a name to be expected to be seen in a Boston uniform for years to come.
Early, on the other hand, may not have the popularity that Tolle does, but he is just as good, if not better. Drafted out of the University of Virginia in 2023, Early has been one of the biggest strikeout pitchers since his debut. In his major league debut, he tied Don Aase for the most strikeouts in a Red Sox debut with 11. He’s been a big part of the elite pitching staff that Boston possesses this season (as has Tolle). Like Anthony, though, he’s on the injured list right now too. It’s a big loss for a team trying to get back to winning.
It is safe to say that both of these pitchers have been huge hits for Boston and Craig Breslow this decade (although Breslow did not draft Early), but both Early and Tolle should be big pieces for the future of this Red Sox team, no matter which direction they decide to go at the trade deadline.
The Last Word
It’s pretty clear that based on the five names here, the Red Sox have had pretty good drafts the past few years, at least when it comes to top-end talent. Except for Meidroth, it seems as if everyone else here will play a big part in the next era for the Red Sox. Hopefully, on July 11th, Breslow can make picks that add even more to the future.
Main Photo Credit: Joe Nicholson-Imagn Images
