How Red Sox 21-Year-Old Rising Star Looked in First Double-A Game

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Anthony Eyanson's Double-A debut went about as well as the Boston Red Sox could have hoped.
On Sunday, Eyanson pitched for the Portland Sea Dogs for the first time after blitzing through High-A in his professional debut. The 2025 third-round pick only needed five starts to earn his way up to within two levels of the major leagues, and he certainly didn't look overmatched by his new level of competition.
Against the Toronto Blue Jays' Double-A affiliate, the New Hampshire Fisher Cats, Eyanson worked four very solid innings, allowing just one earned run on a solo homer in the second inning. He struck out four batters, walked one, and let up three hits.
Anthony Eyanson has completed his first start for the @PortlandSeaDogs.
— Tyler Milliken (@tylermilliken_) May 10, 2026
4 IP - 68 Pitches/37 Strikes
3 Hits
1 ER/R
4 K
1 BB
1 HR
11 Whiffs
Finished his day with back to back Ks. 1-2-3 4th. Victor Arias took him deep in the 2nd to finish a 7-pitch AB. pic.twitter.com/pFEPRBZjGk
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Eyanson's day goes smoothly as fast climb continues

In the clip above, you can really see the depth of Eyanson's curveball from the broadcast view. That pitch could open the door to the majors for the 21-year-old, who the Red Sox somehow stole with the 87th overall pick last July by giving him a $1.75 million signing bonus that was well above his slot value.
On top of that, Eyanson has a fastball that gained somewhere between 5-7 mph in velocity over the offseason and a devastating slider, probably his best pitch overall.
Here's the behind-the-plate view of Eyanson's four strikeouts, courtesy of the Sea Dogs on X:
Welcome to Portland, Anthony 👋 pic.twitter.com/QWGduUGXNB
— Portland Sea Dogs (@PortlandSeaDogs) May 10, 2026
In 24 1/3 innings so far this season, Eyanson has struck out a gaudy 38 batters, allowed just two earned runs, and only surrendered 10 hits. It's safe to say minor-league batters are struggling to figure him out, because his stuff is already bordering on major league quality.
Last season, we saw Payton Tolle climb from High-A to the majors by the end of August, and he wasn't promoted to Double-A until mid-June. Eyanson being at that level by early May doesn't mean he'll make it to the majors as fast or faster than Tolle, but it's certainly a sign that the Red Sox are willing to be aggressive in promoting him if he keeps passing tests.
The first section of his Double-A exam was certainly a pass. We'll see from this point forward how he adjusts, because he's one of the most exciting developments in the entire organization.

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@moreviewsmedia.com