The Red Sox made a significant move to acquire three-time All-Star Adley Rutschman from the division rival Orioles before Monday evening’s trade deadline.
In exchange for Rutschman, backup catcher Jake Rogers, and cash considerations, Boston traded backstop Carlos Narvaez, minor league right-handers Anthony Eyanson and Kyson Witherspoon, minor league outfielder Enddy Azocar, and a player to be named later or cash considerations to Baltimore.
This article will focus on the three prospects switching sides in this blockbuster: Eyanson, Witherspoon, and Azocar. Baseball America had Eyanson as Boston’s No. 2 prospect, while Witherspoon and Azocar were ranked No. 3 and No. 5 in the system, respectively.
Eyanson, the No. 33 prospect in baseball according to Baseball America, is the headliner of the package going back to the Orioles. The 21-year-old right-hander was selected by the Red Sox in the third round (87th overall) of last summer’s draft out of Louisiana State. He received an above-slot $1.75 million signing bonus and is now four months into his first full professional season.
In 16 outings (15 starts) between High-A Greenville and Double-A Portland, Eyanson posted a 1.32 ERA with 94 strikeouts to 26 walks over 68 1/3 innings in which opponents batted .152 against him. He represented the Red Sox in the All-Star Futures Game and struck out a career-high of 10 in his last start with the organization on July 31.
Eyanson worked to add power to his arsenal and raise his arm slot over the winter. The 6-foot-2, 208-pound righty showed encouraging signs in his first spring training and has only taken off from there. He now operates with a 92-95 mph fastball that has topped out at 97.5 mph in-season while also featuring a mid-80s gyro slider, a high-70s curveball, a mid-80s splitter, and a high-80s cutter.
Witherspoon, who turns 22 next week, is ranked by Baseball America as the No. 97 prospect in baseball. The young right-hander was selected by the Red Sox with the 15th overall pick in last summer’s draft out of Oklahoma. He received a below-slot $5 million signing bonus and, like Eyanson, made his professional debut with Greenville in April.
Unlike Eyanson, though, Witherspoon has not had the smoothest of transitions to pro ball. In 17 starts for Greenville, he posted a 4.78 ERA with 78 strikeouts to 34 walks over 75 1/3 innings in which opponents batted .256 against him. His best stretch came from May 24-June 26, when he forged a 2.64 ERA across six starts (30 2/3 innings). He then pitched to a 4.91 ERA in four July outings.
Despite the inconsistencies that have come with some mechanical adjustments, Eyanson still boasts plenty of potential. Now working with a delivery closer to what he was doing at Oklahoma, the 6-foot-2, 206-pound righty sits in the mid-90s with a fastball that has been up to 97.6 mph this season. He also throws a slider, cutter, and curveball.
Azocar, unlike Eyanson and Witherspoon, is not ranked within Baseball America’s top 100. The 19-year-old Venezuelan originally signed with the Red Sox for $40,000 as an international free agent in January 2024. He made his professional debut in the Dominican Summer League that season, then started turning heads as he worked his way from the Florida Complex League to Low-A Salem in 2025.
In 85 games between Salem and Greenville to begin the 2026 campaign, Azocar batted .286/.341/.540 with 27 doubles, six triples, 18 home runs, 63 RBIs, 76 runs scored, 11 stolen bases, 28 walks, and 95 strikeouts over 399 plate appearances. The right-handed hitter slashed .343/.400/.685 in 80 plate appearances against lefties and .272/.326/.503 in 319 plate appearances against righties.
Defensively, Azocar saw most of his playing time this season come in center field. Across 70 total starts (40 with Greenville, 30 with Salem), the athletic 6-foot-2, 195-pounder committed only two errors and recorded four assists in 156 chances over 614 1/3 innings. He also made one start in left, one start in right, and 13 starts at DH between the two stops.
Immediately following Monday’s trade, Eyanson was assigned to the Orioles’ Double-A Chesapeake affiliate. Witherspoon and Azocar, on the other hand, were assigned to High-A Frederick.
(Picture of Anthony Eyanson: Emilee Chinn/Getty Images)