We are two weeks away from the 2026 MLB Draft so its time to take a look back at the first draft of the Craig Breslow era with the Boston Red Sox. Two picks made it big so far while the rest is a mixed bag. Let's see how things are going.
1st Round - OF Braden Montgomery
The good news is Braden Montgomery looks to be a star in the making, the bad news is its not with the Red Sox. Braden was projected to go in the top 5 of the draft but suffered a catastrophic ankle injury with Texas A&M in the NCAA playoffs. Because of the injury, he fell all the way to pick 12 where the Sox took him. He never got to play in the organization because while he was recovering, the Sox traded him to the Chicago White Sox for Garrett Crochet with Chase Meidroth, Kyle Teel and Wikelman Gonzalez. Last year Montgomery cruised through Single A batting a combined .304 with 11 home runs at both levels before finishing the season with AA Birmingham hitting .272. This year he made his ML debut on June 9th and hit a walkoff home run. He's only hitting .243 with 2 home runs but at 23 years old, he'll have plenty of chances to perform. The Sox traded four stud prospects to get an ace and the only reason people are second guessing the trade is Garrett Crochet got hurt and might miss the entire year with a shoulder tear. Montgomery is the future, too bad its not with Boston.
2nd Round - LHP Payton Tolle
Learning from his predecessor Chaim Bloom, Breslow actually drafted a pitcher in the top 50 rather than a high school infielder. Left handed pitcher Payton Tolle was taken 50th overall in the second round and to say he's becoming a fan favorite in Boston is an understatement. He blew through all three levels in 2025 going 3-5 with a 3.04 ERA for the Greenville Drive, Portland Sea Dogs and Worcester Red Sox. Mostly due to injuries and incompetence, Payton made his ML debut on August 29th and pitched in 7 games going 0-1 with a 6.06 ERA. He started this year in Worcester but the injury to Garrett Crochet summoned him and he's been an anchor so far. He's 4-6 with a 3.39 ERA and with any other offense you could flip the record or better. When healthy, the trio of Tolle, Crochet and Connelly Early are going to be deadly for years to come.
3rd Round - RHP Brandon Neely
For every bit right Breslow was with Payton Tolle, the opposite happened in the third round when they selected Florida University right handed pitcher Brandon Neely. Neely looked to be the closer of the future when he saved 13 games for the Gators in 2023 but they made him a reliever and a starter in 2024 where he wasn't very good, jacking his ERA to over 5. Taken by the Sox, the overuse got to him as he didn't pitch at all in 2025 and has been straight batting practice as a starter for Greenville. He hasn't pitched in two years so the Sox might give him another year. Otherwise this is headed toward bust territory real quick. No one else has made it to the majors yet from the third round, so there's that.
4th Round - INF Zach Ehrhard
The guy so nice they drafted him twice. Chaim Bloom took Wharton High School shortstop Zach Ehrhard in the 13th round back in 2021 but he chose to go to Oklahoma State instead. When he came out a second time, the Sox picked him in the fourth round in 2024. Zach hit .272 with 14 home runs between Greenville and Portland in 2025 when he was shipped along with James Tibbs to the Los Angeles Dodgers for pitcher Dustin May. This might be one of the worst trades in franchise history because both Tibbs and Ehrhard are stars for the Oklahoma City Comets. Zach is hitting .282 with 12 home runs and will either make his debut with the Dodgers pretty soon or will be traded somewhere he can. The fact the Sox gave up the careers of Tibbs and Ehrhard for one lousy month of Dustin May is an indictment on Craig Breslow. However, you can't fault Bloom or Breslow for taking a guy that's headed toward the majors.
5th Round - LHP Brandon Clarke
The opposite of Zach Ehrhard is fifth round pick, left handed pitcher Brandon Clarke. Clarke was a mediocre starting pitcher in junior college that for some reason, Breslow thought he could be fixed. He allowed just 1 run in 9 inning for the Salem Red Sox before being promoted to Greenville. He then suffered a left shoulder injury after going 0-3 with a 5.08 ERA in 14 starts. In the off-season he was traded along with "Big" Dick Fitts to the St. Louis Cardinals for Sonny Gray. Unlike the Ehrhard trade, this worked out great for the Red Sox. Gray has been the defacto ace, going 9-1 with a 2.69 ERA for Boston this year with Crochet out. Clarke still hasn't pitched yet this year coming off shoulder surgery. He was drafted because he could hit 99 on the gun, but if surgery takes some of the velocity away, the Sox were wise to trade him.
6th Round - RHP Blake Aita
Speaking of trades with the St. Louis Cardinals, here's right handed pitcher Blake Aita. Taken in the sixth round of the 2024 draft, Blake was 5-7 with a 3.98 ERA between Salem and Greenville in 2025 when he was shipped along with Hunter Dobbins to the Cardinals for Willson Contreras, the hothead leading the Red Sox in home runs this season. Blake is currently 2-3 with a 3.92 ERA for the High A Peoria Chiefs in 14 starts so far. To get your best hitter (which isn't saying much on this year's team) for a prospect still in Single A six months later isn't a bad trade at all. Unless Willson is traded at the deadline and Aita becomes a star, because the Gods hate the Red Sox that much.
7th Round - OF Will Turner
If you're into launch angle then 7th round pick Will Turner out of South Alabama University is your guy. He immediately crapped the bed in Greenville to end 2024 by getting just 6 hits in 74 at-bats and last year hit a whopping .161 for Greenville in 2025. This year he's hitting .202 but at least has 9 home runs. This looks like a misfire and a half and apart from Montgomery falling into Breslow's lap, the position player side of things doesn't look good so far. At least no one else from the 7th round has made it either.
8th Round - OF Conrad Cason
The Sox used their eighth round pick on duel threat pitcher/outfielder Conrad Cason out of Greater Atlanta Christian High School. He only played in 2 games for the Florida Complex Red Sox last year and has only played 4 games this year. Much like the Dominican teenagers, the Sox are going to bring Cason along slowly. He doesn't even turn 20 until August 7th so he's got a long way to go. Still, he might hit better than Will Turner already.
9th Round - C Hudson White
Another misfire was taking Arkansas catcher Hudson White with their 9th round pick. White hit .167 in 18 games for Greenville to end 2024 then just .188 in 70 games last year. This year he's hitting .214 in 17 games and this might be it for him. If you can't hit Single A pitching, how are you going to hit AA or get to AAA? He hit .297 with 8 home runs for Arkansas so its not like he was a bum in college. Just another failed 9th round picks in a sea full of them.
10th Round - LHP Devin Futrell
The Sox might have something in their 10th round pick, left handed pitcher Devin Futrell out of Vanderbilt University. The junkballer came storming out of the gate last year going 3-5 with a 1.87 ERA in 17 starts between Salem and Greenville. This year he started with the Salem Ridge Yaks before being promoted to Greenville. He's 4-0 with a 3.64 ERA in 10 games so far for the Drive and those aren't eye popping numbers, but he hasn't sucked either. It might be time to see what he can do in Portland pretty soon. How sad is the 10th round pick is outperforming the 3rd?
11th Round - RHP Steven Brooks
It seems to be a common theme for Red Sox general managers to draft pitchers who were lousy in college and think they can fix them. 11th round pick, right handed pitcher Steven Brooks was one of them. His 3 year run at Cal Poly saw him go 9-11 with an ERA over 5. For whatever reason Craig Breslow said "Oooooh that's good!" and took him. He was 3-6 with a 5.29 ERA last year for the Salem Red Sox and is currently 1-4 with a 4.23 ERA out of the bullpen. Not the worst but not the best either. The Sox are going to wait another year to see what he can do out of the bullpen before making a decision to cut him or not. Once again, nobody else in the 11th round has made the majors so no big loss yet.
12th Round - RHP Brady Tygart
Another swing and a miss appears to be 12th round pick, right handed pitcher Brady Tygart. Tygart was projected to go in the top five rounds but injuries to his elbow dropped him all the way to the 12th round. He pitched in just 6 games last year between Salem & Greenville and he's been straight batting practice this year for Salem going 1-2 with a 9.42 ERA. If he gets Tommy John surgery, he might be done for good. A shame, if he was healthy he might have been good. Maybe next year.
13th Round - LHP Shea Sprague
Another guy having a bad year this year is 13th round pick, left handed pitcher Shea Sprague. He was a junkballer out of UNC who had a decent season in 2025, going 4-6 with a 4.82 ERA between Salem and Greenville. This year he got lit up in Greenville and made one start for Portland, allowing EIGHT runs in just an inning. That might have shattered his confidence because his numbers for Greenville are awful, 1-2 with a 7.36 ERA. Maybe they brought him up too soon, who knows. Either way if he's getting lit up now, he might need another year to work through this. Good luck.
14th Round - RHP Alex Bouchard
Another potential bust could be 14th round pick, right handed pitcher Alex Bouchard. He was straight batting practice for Lehigh University in 2024 and got lit up for 8 runs in just 5 innings for the Florida Complex in 2025. He also was 0-2 with a 3.63 ERA for Salem to end that season. This year he's 1-3 with a 5.60 ERA. If you wonder why Greenville has a sub .500 record this year, Breslow's 2024 draft class isn't doing so well.
15th Round - RHP Joey Gartrell
You think Greenville has all the 2024 pitchers stinking it up? WELL YOU'RE WRONG! HAHAHA! The Sox took right handed pitcher Joey Gartrell in the 15th round after he was batting practice for Portland University. Nothing changed as he was 3-4 with a 6.81 ERA for Salem last year and is 2-1 with a 5.40 ERA between Salem and Greenville out of the bullpen. When you get demoted from High A to Low A, you know something went terribly wrong. Still, when you draft someone who wasn't good in college, expecting him to be good in the pro's is a fool's errand.
16th Round - RHP Griffin Kilander
Another guy struggling is 16th round pick, right handed pitcher Griffin Kilander out of Wayne State University. He allowed 1 run in 7 innings for the Salem Red Sox at the end of 2024 but was 6-5 with a 4.34 ERA for Salem in 2025. This year he's 0-1 with a 4.74 ERA out of the bullpen for Salem and Greenville. The good news is he's allowed just 2 runs in 9 innings for Greenville. Maybe its the start of him moving on to better things......oh who are we kidding?
17th Round - OF Yan Cruz
The first REAL bust for the Sox came in the 17th round when they drafted 17 year old Puerto Rican outfielder Yan Cruz. He hit just .155 in 43 games for the Florida Complex Sox in 2025 and was released in Spring Training in 2026. Why they gave up on him so quick is anyone's guess and just as an example, the San Diego Padres took Ryan Jackson just three picks after Cruz. Jackson is hitting .264 with a home run for the San Antonio Missions in Double A. Not exactly popping numbers, but that's more than what the Sox got out of Cruz.
18th Round - RHP Cole Tolbert
Most 18th round picks are cucka anyway and right handed pitcher Cole Tolbert might be the exception. After putting up an ERA over 7 for Mississippi University, he put up an ERA of 5.56 to end 2024 with Salem. He got Tommy John surgery in March of last year and this year....he's been good for Salem. He's 1-1 with a 2.66 ERA in 7 starts and a promotion to Greenville might be in the cards. If the TJ worked, they might have something here.
19th Round - INF D'Angelo Ortiz
Nothing like good ol fashioned nepotism! In the 19th round the Sox took Miami Dade Community College infielder D'Angelo Ortiz. Oh yes, David Ortiz' son played in 79 games between the Florida Complex and Salem in 2025 batting .269 with no home runs. This year he's hitting .250 with one home run for the Salem Ridge Yaks and if this was anyone else, he'd be out the door real quick. Only question is how far can he make it on the name since he doesn't have his father's power. Still, rather him hitting .250 & .260 than .190 or .200.
20th Round - RHP Ben Hansen
Well so much for 20th round pick, right handed pitcher Ben Hansen out of Brigham Young University. He was 1-7 with a 6.23 ERA for Salem last year and was 2-0 with a 4.75 ERA for Greenville this year when he was traded literally to the Oakland A's yesterday for 28 year old utility infielder Brett Harris. If you're going to trade someone for a career minor leaguer, guys like Hansen are always the choice. Good luck in Oakland.
RFA - RHP Calvin Bickerstaff
After the 2024 draft was over, the Sox took a flier on right handed pitcher Calvin Bickerstaff out of Kent State University. He allowed 2 runs in 6 innings for Salem to end 2024 and spent 2025 going 4-2 with a 4.32 ERA between the Florida Complex and Salem. This year he was 4-2 with a 3.92 ERA out of the bullpen for Greenville and got a one game cup of coffee with Portland allowing 2 runs in 3 innings. The fact a rookie free agent got 1 game in Portland when about 5 on this list don't even belong in Greenville is an indictment on some of the later round picks. Someone like Bickerstaff had nothing to lose and he's making the best of it.
RFA - RHP Jay Allmer
Another guy with nothing to lose is their other undrafted rookie free agent, right handed pitcher Jay Allmer out of Seton Hall University. Shockingly he was Salem's best relief pitcher in 2025 going 5-1 with a 2.79 ERA with 4 saves before getting a 1 game cup of coffee with Greenville. This year....he crashed down to earth allowing 43 runs in 34 innings between Salem, Greenville and Portland. I don't know what voodoo magic he used in 2025 but its definitely gone now. He won't last much longer with the incoming 2026 draft class unless he turns it back around.
All in all this was a very top heavy draft with two studs in Payton Tolle and Braden Montgomery. A few of them were used in trades they desperately needed but the rest doesn't have any sort of potential at all. The bottom 10 of the draft that hasn't been traded or released doesn't have any standout players. Even Chaim Bloom found diamonds in the rough in Niko Kavadas, Tyler Uberstine and Luis Guerrero. Still, its too early to write it off just yet, but it doesn't look good so far. Just like the 2026 Boston Red Sox really.
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