Revisiting Red Sox's Fateful Quinn Priester Trade Over One Year Later

On April 7, 2025, the Boston Red Sox and Milwaukee Brewers completed a surprise trade. The Red Sox, flush with starting pitching depth, traded Quinn Priester and in return received two minor-league players and a Competitive Balance Round A pick. There wasn't a ton of drama surrounding the deal; Priester was in Triple-A and the Red Sox had other, young pitchers who could provide depth for the rotation. It made sense for Craig Breslow to take a swing at acquiring two young prospects that could help replenish the farm system after an offseason that saw multiple players get shipped out.

The argument against the trade back then was that the Red Sox had put time and effort into helping develop Priester after trading for him less than a year prior. In that deal, they had moved 2020 first-round pick Nick Yorke to the Pirates and immediately kept Priester in Triple-A until the final series of the season. They worked on his pitch arsenal and pitch shape and in the offseason wanted him to gain weight and put on muscle. Upon arriving at spring training, he had done what they asked.

Despite that, the pitcher was optioned to Worcester to open the 2025 season and after just one start where he allowed two runs in four innings, he was traded to the Brewers, who needed starting pitching help at the time.

Unfortunately, later in the year, the Red Sox's rotation began to falter and injuries led to young pitchers like Connolly Early and Payton Tolle needing to step up. It just so happened that Priester immediately responded to Milwaukee's pitching lab, compiling an impressive campaign: he pitched in 29 games (24 starts) and went 13-3 with a 3.32 ERA. He managed to strike out 132 batters in 157 1/3 innings.

The players the Red Sox acquired, Yophery Rodriguez and John Holobetz, weren’t exactly lighting the world on fire either. The biggest value from that trade wound up being the pick the team acquired and eventually used to draft Marcus Phillips. Because of this, the trade was deemed a failure.

At the time, Rodriguez was the only player of note the Sox received, and in his first month he looked rather impressive, hitting .257/.409/.414 with two doubles, three triples, a home run and eight RBIs while walking 17 times. He would unfortunately fall off in May and June before showcasing his talents once more in July, which only gave way to a .147/.234/.235 line in August.

Despite being just 19 years old, many were ready to call Rodriguez a bust. Fortunately, he bounced back to begin 2026 and showed the flashes of the potential that Breslow saw in him. In 19 April games he slashed .310/.380/.662 with seven doubles, six home runs and 12 RBIs and at one point led the entire organization in home runs. The outfielder also showcased great defense in left field.

Unfortunately, much like in 2025, Rodriguez saw a decline at the plate as the season has gone on. May was especially tough as he struck out 19 times and slashed just .192/.270/.385. He's working with an 85 wRC+ while repeating High-A, though he's still just 20 years old. For Rodriguez, to reach his true potential, he’ll need to improve his pitch recognition as he already makes consistent contact on pitches thrown in the zone.

Holobetz arrived as a player to be named later in the trade and was immediately sent to High-A Greenville. He had some quick success there, tossing 63 innings and striking out 62 batters before being promoted to Portland. At that stop, he appeared in six games and tossed 37 2/3 innings and only walked five batters. The right-hander used a four pitch mix of his fastball, slider, curveball and changeup to succeed in Double-A.

Despite his success, he’s likely destined for the bullpen as someone who lacks a strong complementary pitch to a good fastball. Nevertheless, the right-hander has remained in the rotation to continue his development as a starter and so that he can pitch more innings than if he were in the bullpen. In 2026, he tweaked his slider a little, giving it more of a bullet shape, but it hasn’t moved the belief in it being nothing more than an average offering.

In 2026, Holobetz has made 15 appearances and tossed 72 innings with a 4.75 ERA and 26.2% strikeout rate. Much like Rodriguez, Holobetz got off to a fantastic start in 2026 as he allowed just six runs over his first 22 innings. Unfortunately, May was a step back as his innings fell to 19 and he allowed 21 runs, 16 of them earned. Since then, Holobetz has continued to improve as he’s bounced back in June and the discussion about an eventual promotion Worcester has resumed.

The final piece of the trade, Marcus Phillips, is the one that could really make the difference. Phillips is an incredibly talented pitcher who has high reliever risk. Taken 33rd overall, Phillips is best known for his flamethrowing tendencies, thanks to a fastball that tops out at close to 101 mph

For Phillips, he’ll be developed as a starter due to the raw stuff of his pitches. However, unless he works on his control issues, he’s likely destined for the bullpen. In college, he walked 49 batters in 103 innings during his two seasons with Tennessee. So far in 46 innings with Greenville, he’s given up 37 walks.

Of the three players acquired for Priester, Phillips is the most talented of them. However, he also has the highest risk of being a bust. Should the Red Sox manage to turn him into a dominant reliever or a back-end starter, then this trade becomes a success for the Red Sox.

But even if two of the three players they received fail to pan out, the trade isn't a total disaster. Despite Priester’s great 2025 season, 2026 has been a struggle as he opened the year on the injured list and his rehab appearances didn’t go too well (15.75 ERA). Things got so bad that he would go on to have thoracic outlet decompression surgery on June 22. The surgery typically sidelines a pitcher eight to 10 months, putting his 2027 season into question as well.

From that point of view, many could argue that the Red Sox were at least right to make the trade, even though it’s impossible to predict an injury of that degree. Even without that foresight, they received three interesting prospects for one really good season of Priester and two injured years. In Breslow’s case, that should be considered a legitimate success.