The 2026 Major League Baseball Draft gets underway on Saturday afternoon in Philadelphia, kicking off All-Star week festivities. For Boston Red Sox Chief Baseball Officer Craig Breslow, the draft represents an opportunity to continue to add to a rather depleted Red Sox farm system. Despite an underwhelming tenure in the major leagues, Breslow has been a very effective drafter at the helm of the Red Sox. 

Here’s a look back at his first two drafts:

After a disappointing 2023 season that led to the firing of former head of baseball pperations Chaim Bloom, the Red Sox held the 12th overall pick in the 2024 draft, selecting switch-hitting outfielder Braden Montgomery from Texas A&M. Montgomery, who was recovering from a broken ankle suffered during the College World Series, did not play a game in the Boston organization before being dealt to the Chicago White Sox as part of the blockbuster deal that sent 2025 Cy Young runner-up Garrett Crochet to Boston. 

The 23-year-old switch-hitting outfielder tore through the minors in only 775 plate appearances, hitting .284/.381/.477/.858 with the White Sox organization before making his major league debut on June 9. In the 27 games since his promotion, Montgomery is hitting .224/.294/.367/.661 with two home runs. 

The crown jewel of the Red Sox' 2024 class, though, was their second-round pick, a tall left-handed pitcher from Texas Christian University, Payton Tolle. Tolle, of course, tore through the minor leagues, making his major league debut in his first season of professional baseball. The 23-year-old left-hander entered the season as Baseball America's No. 17 prospect before quickly rising into the top 10. 

Tolle has dominated in his time at the big league level in 2026, ranking in the top 10 among all rookie starters in ERA (3.14, 5th), strikeouts per nine innings (8.96, 8th), walks per nine innings (2.64, 4th), and WHIP (1.09, 4th), while being lauded as a future ace by his teammates. 

Other notable selections in the 2024 draft include fifth-round pick right-handed pitcher Brandon Clarke, who posted a 4.03 ERA with a ridiculous 14.21 strikeouts per nine innings in 14 starts in 2025 before being dealt to the St. Louis Cardinals in the deal that brought Sonny Gray to Boston. Also taken was fourth-rounder Zach Ehrhard, who hit .246 in 111 games with the Red Sox organization before being sent to the Dodgers in an ill-fated trade deadline deal for starter Dustin May. 

With the 15th overall pick in the 2025 draft, the Red Sox selected righty Kyson Witherspoon out of the University of Oklahoma. After a rough start to his professional career, in which he posted a 7.18 ERA through his first seven starts, the 21-year-old has bounced back, posting a 4.50 ERA in his last six outings. Witherspoon is currently ranked as the No. 94 prospect in baseball according to Baseball America. 

The Red Sox's second pick was a competitive balance pick acquired from the Milwaukee Brewers in the Quinn Preister trade. With that pick, the Red Sox selected right-handed pitcher Marcus Phillips of the University of Tennessee. It’s been a rough go of things for the 21-year-old in 2026, posting a 6.26 ERA in 14 appearances for High-Greenville. 

With their third selection in 2025, the Red Sox selected infielder Henry Godbout out of the University of Virginia. Godbout has a strong feel for the strike zone and good bat-to-ball skills with room to grow into some power once in the Red Sox system. The 22-year-old was hitting .277/.410/.492/.902 with seven home runs before suffering a broken hand after being hit by a pitch on May 30. 

Of course, the crown jewel of the Red Sox' 2025 draft class thus far is right-handed pitcher Anthony Eyanson, who was selected out of Louisiana State University in the third round. Eyanson burst onto the scene in 2026, allowing just one earned run in his first five professional starts with Greenville, striking out 47.9 percent of the batters he faced.

Boston quickly promoted the 21-year-old to Double-A, where he has posted a 1.78 ERA in eight appearances. He is currently the No. 33 prospect in baseball and will, alongside shortstop Franklin Arias, represent the Red Sox in Sunday's Futures Game.

Other notable selections in the 2025 draft include 13th-rounder third baseman Jack Winnay. The 23-year-old Wake Forest product hit .255/.434/.457/.891 with 11 home runs in 56 games with Greenville before being promoted to Portland on June 23. In his first 14 games for the Sea Dogs, Winnay has been impressive, hitting .327/.393/.491/.884 with two home runs. He is currently the No. 25 prospect in the Boston organization per SoxProspects.com. 

Breslow will look to keep his hot streak going, starting with the 20th overall pick on Saturday afternoon. 

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