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At times, the Red Sox have been accused of hoarding prospects rather than accepting the necessary risks to pursue titles. Monday’s trade to land Adley Rutschman from the Orioles will not suffer such accusations.
In exchange for Rutschman, backup catcher Jake Rogers, and cash, the Sox sent a prospect haul: righthanders Anthony Eyanson and Kyson Witherspoon, outfielder Enddy Azocar, and big league catcher Carlos Narváez. The Sox also will send a player to be named later to the Orioles.
It’s arguably the costliest Sox deadline deal in terms of young, controllable talent since at least 2009, when the Sox landed another All-Star catcher, Victor Martinez, in exchange for Justin Masterson as well as minor leaguers Nick Hagadone and Bryan Price.
The Sox have made other moves involving top prospects at the deadline. In 2016, they sent prized righthander Anderson Espinoza to the Padres for All-Star Drew Pomeranz. In 2013, they parted with infielder José Iglesias to land Jake Peavy. But to land Rutschman, the Sox traded three of their five top-ranked prospects — a dredging of the system rarely seen.
“At this time of year when you are trying to improve your team, there are not deals that are comfortable,” said chief baseball officer Craig Breslow. “You try to remain as disciplined as you can, but I think you have to constantly zoom out to remind yourself that what you’re trying to do is improve your major league team in this season.”
Eyanson is the headliner. A 2025 third-rounder, he ranked as the No. 2 prospect in the system and the No. 33 prospect in Baseball America’s most recent update. He entered pro ball with a pair of impressive breaking balls (curveball, slider) but a low-90s fastball that was light enough to raise questions about whether he could start.
But Eyanson made huge physical and stuff gains thanks to his commitment to the team’s offseason training program. In the spring prospect breakout game — against the Orioles, no less — he touched triple digits for the first time.
The improved velocity, two breaking balls, and an improved splitter gave hitters fits this year.
In 68⅓ innings this year between High-A Greenville and Double-A Portland, he posted a 1.32 ERA with a 37 percent strikeout rate. Evaluators did have some concern about his velocity tapering off as the season progressed, but there’s significant belief Eyanson is a future big league starter, perhaps in the upper half of a rotation.
“The pitcher is special,” said one NL evaluator.
Witherspoon, a 2025 first-rounder, was the team’s No. 3 prospect and No. 97 in the game. He made a rocky entry into pro ball this year while working through mechanical adjustments, and carried a 7.18 ERA through seven starts in Greenville. Scouts sounded alarms.
But Witherspoon clawed his way back, working to re-establish his delivery while forging a 3.49 ERA with a 26 percent strikeout rate in his last 10 starts. That moved him back into top-100 status.
Azocar, 19, was tabbed as a potential breakout player entering this year and didn’t disappoint. He dominated to start the year in Single-A Salem (.295/.344/.530 with six homers in 39 games) and remained impressive after a promotion to High-A Greenville (.279/.338/.547 with 12 home runs in 46 games).
Though far from the big leagues, he’s a dynamic talent with above-average defensive and power potential, albeit with an aggressive approach that gave less certainty to his future as a hitter. Still, he has a chance to be a multidimensional, everyday player, and some viewed him as the best Sox positional prospect behind shortstop Franklin Arias.
Narváez is more of a known. After a strong 2025 campaign, he was underwater as a hitter for most of the year (.187/.260/.275 with a 34 percent strikeout rate). Still, he commanded trust from the pitching staff, and the Sox were 28-28 in games he started behind the plate.
The package the Sox sent to Baltimore is comparable to the one they sent to the White Sox for Garrett Crochet in December 2024. That deal likewise featured a pair of top-100 prospects, with Eyanson nearly matching the industry value of catcher Kyle Teel as a headliner. Witherspoon doesn’t quite match the industry value of outfielder Braden Montgomery but also is a top-100 player. Azocar has a higher ceiling than infielder Chase Meidroth but a less-established floor. Narváez is a big leaguer, whereas righthander Wikelman Gonzalez was a lottery ticket.
“[The] Orioles did well here,” said one scout. “[The] Red Sox gave up a lot.”
But for the Sox, the deal allowed them to get Rutschman, a potential difference-maker at a position where they have struggled. They kept Arias, who has a chance to help this year. And the willingness to include Eyanson and Witherspoon less than two weeks after dealing Connelly Early attested to their belief that they have forged a renewable pitching pipeline.
The Sox felt like this was a deal they were positioned to make — a high-risk gamble for a team looking to keep riding one of the greatest hot streaks in franchise history.
“They paid a lot. They got a really good player,” said one AL evaluator. “That’s how this [stuff] is supposed to work.”
Alex Speier can be reached at alex.speier@globe.com. Follow him @alexspeier.