Brutal Red Sox trade whiff hurts even more at the trade deadline

Boston's early-season trade of Quinn Priester has left the front office scrambling in July.
Boston Red Sox v Pittsburgh Pirates
Boston Red Sox v Pittsburgh Pirates | Kevin Sabitus/GettyImages

The Boston Red Sox struck a deal with the Milwaukee Brewers in April, sending 24-year-old righty Quinn Priester to the great midwest in exchange for 2024 fifth-round pick John Holobetz, No. 7 Brewers prospect Yophery Rodriguez, and the No. 33 pick in the 2025 MLB Draft, which turned into Tennessee right-handed pitcher Marcus Phillips, MLB Pipeline's No. 61-ranked prospect.

Overall it's an impressive haul for the Red Sox, who acquired Priester midway through the 2024 campaign and only saw him once in a big-league uniform. After signing the likes of Walker Buehler in free agency and welcoming back Lucas Giolito from injury, the Red Sox clearly felt Priester was expendable. So naturally, Boston is bending over backward to find pitching help at the trade deadline.

Boston's rotation has been up and down all season. Giolito began ice-cold upon his return from Tommy John surgery, only to heat up in the weeks before the All-Star break. In Friday's loss to the Cubs, however, which ended a 10-game Red Sox win streak, Giolito gave up four earned runs in 5.1 innings, including a three-run moonshot from Seiya Suzuki in the first inning.

Brayan Bello is another key member of the Red Sox rotation whose production has fluctuated throughout the campaign. Factor in various injuries to Buehler, Tanner Houck, Hunter Dobbins and Kutter Crawford (among others), and it has been very difficult for Boston to field a solid five-man rotation this season. If only Priester was still around.

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Red Sox undoubtedly regret Quinn Priester trade given current state of roster

Boston came away from the Priester trade with significant long-term value, but that entire return package — Rodriguez, 19, Holobetz, 22, and Phillips, 20 — consists of players who are years away from MLB production. Very little is actually guaranteed that early in the developmental track and Boston is clearly in win-now mode. It wouldn't be completely shocking if some of the very same assets from the Priester trade are rerouted to acquire another more MLB-ready pitcher at the deadline.

Priester, for what it's worth, does indeed look ready for the big leagues in Milwaukee. Through 18 appearances and 13 starts this season, the sinker-baller is producing grounders at a 95th percentile rate, to the tune of a 3.33 ERA and 1.20 WHIP. His 0.9 fWAR would be tied for third in the Red Sox rotation, trailing only Garrett Crochet (4.3) and Giolito (1.4). And Priester hasn't even been starting the whole season.

Boston tied to several pitchers ahead of the July 31 deadline

If there's a silver lining here for Boston, aside from the long-term potential of the aforementioned prospects, it's that Priester is relatively green at the MLB level. He made 15 starts for Pittsburgh between 2023 and 2024, but he lacks postseason experience, which is where Boston is aiming right now. It's unclear how ready Priester would be to start games in such a high-pressure environment. His lack of swing-and-miss stuff could prove faulty if he's not on his A-game come October.

So the Red Sox will instead target more proven names, such as Minnesota ace Joe Ryan or Arizona flamethrower Zac Gallen. It's clear Craig Breslow and the front office feel empowered to operate aggressively after the Rafael Devers trade, not to mention their recent surge in the standings. So while the Priester trade feels like a slight miscalculation on their part, Boston's brass can right the ship in a big way over the coming days and weeks.