The Major League Baseball Draft is fast approaching, with two weeks until draft night. It’s always tough trying to gauge how prospects will turn out. But since 2020, the Boston Red Sox have missed out on a few big players who have had successful careers thus far. General Managers also aren’t always perfect at selections, sometimes picking better prospects over potential. Hindsight’s always 20/20, so here are the five biggest missed opportunities of the decade for the Red Sox.
Criteria
First off, a couple of big criteria for this list.
- They have to have made the majors at this point. There will be no players from 2025 on this list, as they haven’t made their major league debuts yet. Minor league play is entirely different from major league play. As seen by someone like Kristian Campbell, a player can win Minor League Player of the Year and flame out in the majors.
- A player who missed must be drafted in the same round as the player the Red Sox have drafted. For example, Chase Burns was originally drafted in the 20th round of the 2021 draft. He was in high school, and no one predicted what he would become yet. He later opted out and got drafted second overall in 2024. So it’d be unfair to say something like “They should’ve drafted Burns in the fourth round”.
HMs: Jeremy Wu-Yelland over Spencer Strider, Christopher Troye over Ben Rice
Braden Montgomery Over Trey Yesavage
Because it’s so early in both of these players’ careers, this will be talked about first. Braden Montgomery was a very good prospect. Coming out of Texas A&M, he was fresh off a season where he hit .322 with 27 homers and drove in 85 RBIs. This was good enough to get him selected 12th overall in the first round. With a hitter like that, it would be weird not to take him in a redraft. Except the Red Sox had a surplus of outfielders. There was no clear path for Montgomery to get a spot with them, which is why he was a big part of the trade to acquire ace Garrett Crochet.
Speaking of pitching, however, eight picks later at 20th overall, the Toronto Blue Jays picked Trey Yesavage, a right-handed pitcher from East Carolina. He was coming off a spectacular season where he went 11-1 with an ERA of 2.03. Unlike Montgomery, who made the College World Series Championship, Yesavage and ECU were eliminated in the regional final. However, Yesavage rose quickly through Toronto’s system and ended up being a September call-up.
He would be added to the postseason roster as well, making a huge impact against the Los Angeles Dodgers in the World Series with a 2.84 ERA across three starts. Montgomery wasn’t a bad pick by any means, but given that Boston needed pitching depth badly going into the 2025 postseason, a guy like Yesavage would’ve been a good pick.
Jud Fabian Over Andrew Abbott
In the second round of the 2021 draft (40th overall), the Red Sox would draft Jud Fabian, a slugging catcher who hit 20 homers but failed to hit above .250. They drafted him, but he opted to return to the University of Florida instead. However, there was yet again a pitching prospect the Red Sox missed out on.
There goes the second-round draft pick for the Red Sox. Deadline is tomorrow at 5 p.m., but Jud Fabian tweets that he’s coming as a Gator in 2021. https://t.co/uvoMukrGZt
— Ian Browne (@IanMBrowne) July 31, 2021
The pitcher in question was Andrew Abbott (53rd overall), a pitcher who’s been successful with the Cincinnati Reds. While he may not be the biggest name out there, he has been a solid pitcher since his debut in 2023. Owning a career record of 33-27 and an All-Star appearance in 2025. That year, he went 10-7 with a 2.87 ERA, also throwing a complete game shutout on June 10th. Again, one of the Red Sox’s problems this decade has been top-tier pitching. They have had a lot of depth, but not quite one of the best rotations overall.
Caleb Bolden Over Cam Schlittler
The pick that inspired the idea for this list, Caleb Bolden (219th pick), was selected in the seventh round of the 2022 draft. A mix between a starter and a reliever, in the year of the draft, he went 5-2 for TCU in 23 appearances. Since then, he’s struggled in the minors, having ERAs of at least 4.50 in back-to-back years with the Portland Sea Dogs.
Who went one pick later at 220? Only current Cy Young candidate (and local kid) Cam Schlittler. The ace from Walpole, Massachusetts, is 8-4 this year with a 1.62 ERA and has dominated the Red Sox in his four outings against them, including last year’s Wild Card series. When he threw eight innings of shutout baseball, striking out 12 and out dueling Connelly Early. The Red Sox pitching staff is really solid this year, but with Crochet out and Brayan Bello going through struggles, it would be nice to have a guy like Schlittler here.
Nick Yorke Over Pete Crow Armstrong
To take a quick break from the pitchers that they missed, here’s a rare occasion that a first-round pick was a complete miss. In 2020, the Red Sox drafted infielder Nick Yorke with the 17th overall pick. Yorke had his ups and downs in the minors, struggling in Greenville in 2022, but killing it in Worcester in ‘24. He would later be traded to the Pittsburgh Pirates in exchange for Quinn Priester.
But just two picks later, at 19, the New York Mets selected Pete Crow-Armstrong, an outfielder who has since been traded to the Chicago Cubs. In 2025, he became one of the youngest outfielders to have a 30-home-run, 30-stolen-bases season. He would make an All-Star appearance that year as well. This year, he has 17 and 18, respectively, but he’s also hitting .284 and has 13 DRS. At that point, Boston did not have Roman Anthony in the system or Wilyer Abreu. Jarren Duran and Ceddanne Rafaela were not up yet either. Throwing Crow-Armstrong in the mix could’ve made the best outfield in the majors even stronger.
Cutter Coffey Over Jacob Misiorowski
While no one could have predicted this meteoric rise that Jacob Misiorowski has had, he was a second-round pick after his tremendous season at Crowder College. Going 10-0 with a 2.72 ERA in his sophomore season, he brought instant attention when his fastball averaged 99.8 at the 2022 MLB Draft Combine.
Fast forward to 2026, and he’s consistently throwing over 100 and is one of, if not the, best pitchers in baseball. He was drafted at 63rd overall in the second round, while the Red Sox picked Cutter Coffey at 41, a third baseman who has since left the system. But it wasn’t just the Milwaukee Brewers’ ace. Parker Messick was also drafted in the second round of ‘22, at 54th overall.
The Last Word: One Big Takeaway
These are five of the biggest misses of the Red Sox’s drafting history for the 2020’s. As seen above, there are some pretty notable players here, mainly pitchers. The Red Sox rotation in 2026 is spectacular, even without Crochet. But what is proven here is that if Boston drafted correctly, it wouldn’t need to look in the free agent pool for pitchers and could spend it in other areas. The Red Sox have had their fair share of hits, though, which will be covered soon.
Main Photo Credit: David Butler II-Imagn Images
