As of last night, the Double-A Chesapeake season got under way. The highest-level Orioles affiliate that you don’t have to leave Maryland to watch is always a place with prospects to watch, at least as long as the Orioles farm system is well-stocked with prospects worth watching.
This affiliate had a lot going for it all through last season, starting with several players who are now in Norfolk, including pitching prospect Trey Gibson and outfielder Enrique Bradfield Jr., all the way to the end with some
late-season promotions of pitchers like Luis De León and the since-traded (for Shane Baz) Michael Forret. It didn’t really translate to wins and losses for the Baysox team itself, as they ended up with a 59-77 record a year ago.
Orioles top 30 prospects
- LHP Luis De León
- 2B/OF Aron Estrada
- RHP Tyson Neighbors
- OF Thomas Sosa
- C/1B Ethan Anderson
- SS Griff O’Ferrall
With Samuel Basallo and Dylan Beavers graduating out of prospect status in the early days of the 2026 MLB season, the Orioles system is now down to just one player on the current MLB Pipeline Top 100 prospects list. That’s outfielder Nate George, who will be beginning the season at Frederick.
One of the key stories for the organization as this year goes along is whether they can develop some more of their talent into top prospects who will either contribute to the MLB club or headline trades for established stars. If this happens, Chesapeake will probably be a place that plays witness to it. The highest-placed prospect here, De León, is now the #2 prospect in the Orioles system, and the top pitcher in the system. Can the Orioles finally develop a homegrown player into a useful starting pitcher for the MLB team?
Estrada, my current favorite outside of the top-tier prospects, is young, having just turned 21 in January. He just keeps getting interesting results while being a young guy for the levels he’s played. This included last year when, at Aberdeen, a place that was cursed for hitters, Estrada was able to bat .284/.369/.429 before getting promoted to Chesapeake. The scouting world isn’t sure what position he’ll be able to play at higher levels and he will have to keep proving the doubters wrong by hitting at each level also.
Sometimes guys like that end up like Trey Mancini. Sometimes they end up like Connor Norby. Sometimes they end up like Frederick Bencosme, a Baysox teammate who, if you remember that you’ve heard his name before just now, you’re an Orioles prospect sicko.
Neighbors is one of the players the Orioles got in the O’Hearn/Laureano trade with the Padres last year. He is, in fact, the closest to the majors from that trade. The reliever had a 0.59 ERA in 12 games after that trade. I hope he’s in Norfolk before long. The team has generally been aggressive in moving its older prospects. This is the age 23 season for Neighbors, which is old to be at Double-A and still be much of a prospect.
The Orioles have been aggressive in promoting Sosa, who only turned 21 in January, despite Sosa never really hitting good at any of the stops lower in the minors. The outfielder with big power potential has been more in what is often described as “holding his own,” which is what you get when you have a player who’s young for the level (he’ll be close to 2.5 years below the average player at Double-A) who is able to avoid completely collapsing numbers. He hit .222/.309/.407 for Aberdeen last year. It’s not good, but it’s good enough for the team to move him up and keep waiting for the breakout at the next level.
Anderson and O’Ferrall were each part of the high picks in the 2024 draft who encountered serious struggles at High-A last year. Anderson is a first baseman/catcher with no power (four homers in 90 games last year) and O’Ferrall is a shortstop/second baseman with no power (four homers in 121 games).
Starting on the injured list
- RHP Braxton Bragg (Tommy John)
- RHP Juaron Watts-Brown (shoulder)
- RHP Patrick Reilly (Tommy John)
When the break camp rosters for the minor league teams were announced, I was surprised that Watts-Brown wasn’t listed on the Chesapeake roster. Now I know why: He’s hurt. I hope he’s recovered soon and can get back to it, because I was excited for hyphenated Team Brown.
Bragg did not have his Tommy John surgery until the end of July last year, so it’s unlikely that he’ll pitch with this affiliate this year. Absolute best case scenario might be if he is able to do a rehab outing or two before Low-A Delmarva’s season ends. Reilly, on the other hand, had his surgery in the middle of May. A return to the Double-A level before this minor league season is through is more realistic, if not guaranteed. Both of these guys were showing some real promise last year before the elbow ligaments went pop. There’s a reason why the acronym TINSTAAPP – there is no such thing as a pitching prospect – is said frequently enough to be understood.
Others who may arrive later
Pretty much anybody who’s starting the year assigned to High-A Frederick, whose roster I’ll be previewing on Monday, is a possibility to make it to Chesapeake at some point during the season. That starts with the guy who is now the #1 prospect in the system, George. It also includes high 2025 draft picks Ike Irish, Wehiwa Aloy, and Joseph Dzierwa. A pitcher, Dzierwa put on a showcase in the Spring Breakout prospect game last month.
Potentially, Vance Honeycutt, who dropped off the radar after flopping at High-A last year, could make his way up a level if his spring home run prowess translates in any way to regular season improvement. Honeycutt or any of the guys from the previous paragraph advancing depends on them actually showing well in Frederick. That’s not guaranteed for anyone, but hopefully it’ll happen for at least a couple of them.
