One of the biggest arms to change hands at this year’s trade deadline has already started making noise in the Orioles system.
Anthony Eyanson took the ball for the Chesapeake Baysox on Saturday and wasted little time showing why Baltimore views him as a major piece of its return. In his first start for the organization, the 21-year-old right-hander worked five innings in a 5-2 Baysox win over the Harrisburg Senators, allowing two runs on four hits and one walk while striking out nine.
Eyanson arrived in the Orioles organization as part of the blockbuster deadline deal that sent three-time All-Star catcher Adley Rutschman to the Boston Red Sox. Boston had made Eyanson its third-round pick in last year’s draft, and he quickly rose to the top of the club’s pitching prospect rankings before getting moved. Now the former LSU standout is opening the next chapter of his career in Baltimore’s pipeline.
The debut fit the profile of what the Orioles were hoping to get. Eyanson has been sharp throughout 2026, posting a 1.47 ERA across 17 minor league games with 103 strikeouts in 73 1/3 innings. He opened his pro career with the High-A Greenville Drive and put up a 0.44 ERA in five starts before moving on to the Double-A Portland Sea Dogs, where he logged a 1.69 ERA in 11 games before the trade.
Baltimore got another first look at a new arm on Saturday, too. Kyson Witherspoon, another prospect acquired in the Rutschman deal, made his first start in the Orioles organization for the High-A Frederick Keys.
The 21-year-old right-hander allowed one unearned run on five hits and five walks over 4 1/3 innings, striking out three. A University of Oklahoma product, Witherspoon was a first-round pick by the Red Sox in last year’s draft.
With both pitchers now settled into their new homes, Orioles fans will have plenty to track as the season winds down. Eyanson’s finish could even help determine whether he opens 2027 in Double-A or Triple-A.
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