Aug 28, 2026 1:07 AM

The Red Sox sent top prospects Anthony Eyanson, Kyson Witherspoon and Enddy Azocar to Baltimore in a trade deadline blockbuster.

The Boston Red Sox made one of the biggest splashes of the trade deadline, landing three-time All-Star catcher Adley Rutschman in a blockbuster deal with the Baltimore Orioles for a package headlined by three of Boston’s top six prospects, Anthony Eyanson, Kyson Witherspoon and Enddy Azocar. Now over three weeks removed from the deadline, we take a look at how the trio has performed with their new team. 

Eyanson

Aside from his former teammate with the Portland Sea Dogs, shortstop Franklin Arias, there may not be a prospect in the sport whose stock rose as much as the 21-year-old right-hander in 2026. After dominating at High-A for the first month of the season, Eyanson was quickly promoted to Double-A where his dominance continued. In 11 appearances for Portland Eyanson allowed only nine earned runs on 28 hits across 48 innings of work, good for a 1.69 ERA and an opponent batting average of .172. 

Eyanson was assigned to Double-A Chesapeake upon being dealt to Baltimore, where his dominant season continued. In four starts with the BaySox, Eyanson has allowed only five earned runs across 21 innings while striking out 32 batters and walking only eight. 

Witherspoon 

It was a tumultuous first professional season for the Red Sox' 2025 first-round selection, as Witherspoon struggled to an ERA of 4.78 across his first 17 starts with High-A Greenville. Among Witherspoon’s biggest problems during his time in Greenville was the penchant to allow the long ball, allowing 1.19 home runs per nine innings. Despite his struggles, the 21-year-old Oklahoma product appeared to turn a corner in his final 10 starts in the Boston organization, posting a 3.49 ERA across 49 innings. 

However, since joining the Baltimore system, Witherspoon has reached another level. In his first three starts with the High-A Frederick Keys, Witherspoon has allowed only two earned runs on nine hits across 14.1 innings, striking out 20 and walking 10, while allowing zero home runs. 

Azocar 

Given Boston’s ability to develop starting pitching under Chief Baseball Officer Craig Breslow, Azocar was arguably the toughest prospect to part with in the deal to land Rutschman. In 85 games with Single-A Salem and High-A Greenville, Azocar hit .286/.341/.550/.891 with 18 home runs and 27 doubles while driving in 63 runs, while playing excellent outfield defense. As a result of his hot start, Azocar rose from the No. 15-rated prospect in the organization to No. 6 according to SoxProspects.com

In 19 games since being dealt to Baltimore, the 19-year-old has continued to swing a great bat, hitting .346/.388/.603/.991 with three home runs, seven doubles, and two triples while cutting his strikeout rate by nearly eight percent. 

Rutschman’s struggles 

While the three biggest pieces of the package heading back to Baltimore haven’t skipped a beat, the same cannot be said for Rutschman, who has yet to get acclimated to his new team. In 12 games since being activated off the injured list, the 28-year-old has struggled to a .146/.255/.244/.499 slash line. 

In addition to his struggles at the plate, Rutschman is battling a sore elbow that kept him out of the lineup for the final two games in Miami on Tuesday and Wednesday, though interim manager Chad Tracy has noted his absences were considered precautionary. 

While it remains far too early to declare a definitive winner of the deal, Baltimore certainly seems to have the early edge. 

Up next for the Red Sox

After taking two of three from the Marlins to kick off a seven-game road trip, the Red Sox will head to the Bronx for a crucial four-game set against the Yankees, trailing New York by only 2.5 games for the top wild-card spot. Patrick Sandoval (1-2, 4.54 ERA) will get the start for the Red Sox in Friday's series opener opposite American League Cy Young Award favorite Cam Schlittler (11-6, 2.16 ERA) for New York. First pitch from Yankee Stadium is set for 7:15 p.m. ET.  

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