Eying the Next Window: Evaluating Baltimore’s Return in the Adley Rutschman Deal

As we analyzed what various teams were likely to do at the deadline, the Orioles were one of the toughest teams to peg. Just a few games under .500 and within shouting distance of the final American League Wild Card spot, Baltimore had a lot of ways to approach the rest of their season. While the Dean Kremer and Taylor Ward deals signaled the club’s intention to sell, the decision to trade Adley Rutschman to Boston not only confirmed Baltimore’s direction for the rest of this season, but also arguably changed the course of the franchise. It’s the end of an era, and a bitter pill to swallow for a fan base barely a half decade removed from “playing badly for Adley.” Not surprisingly, Elias’s claim from exactly four years ago that the competitive window was open in Baltimore (“it’s liftoff from here“) has made the rounds again on social media today.

If it’s any consolation for O’s fans, the prospect package from the Red Sox is quite a haul. In exchange for Rutschman (along with catcher Jake Rogers and cash), the Orioles have acquired prospects Anthony Eyanson, Enddy Azocar, and Kyson Witherspoon, along with catcher Carlos Narváez and a player to be named later or cash. That’s two Top 100 prospects, including a guy in the top 30, and a pitcher who could enter that orbit as well. Let’s touch on each of them individually and then muse a bit about what this means for Baltimore’s system and the franchise overall.

Anthony Eyanson, RHP

Eyanson is one of the breakout prospects of the season. After transferring to LSU for his draft year, the righty notched big numbers with the Tigers, and signed for an over-slot $1.75 million as Boston’s third round selection. After five dominant starts in High-A this spring, he’s spent most of the summer in Double-A Portland, where he’s again been very good: He’s posted a 1.69 ERA with a 32.3% strikeout rate in 48 innings, and hitters are batting a meager .172 against him. He’s walking more guys than he did in Greenville or in college, but this hasn’t dimmed my long-term control and command projections, which remain above average.

Eyanson is throwing a little harder this year than he did in school. While he’s not reliably sitting in the 97-99 mph band he flashed in Boston’s Spring Breakout Game, he’s been able to pitch at 92-96 and touch 98 with 18 inches of vertical break. His slider, curve, cutter, and split are all flashing plus, and the breaking balls in particular are playing that way. He has a high release and an overhand slot, and the angle is giving hitters fits, particularly on his secondaries, which seem to be tough for opponents to identify out of the hand.

A good athlete with a controlled, up-tempo delivery, Eyanson has thrown strikes throughout his career. He’s walking more guys than usual right now, in part because he’s trying to coax a lot of chase; with the fastball in particular, he can get in ruts where he misses too far out of the zone to entice hitters. I imagine he’ll hone that skill as he progresses in his career. For now, I’m impressed that he can move the fastball up and down and use his secondaries to both steal strikes and generate whiffs beneath the zone.

Going forward, Eyanson is a good fit for Baltimore’s dev system. The Orioles like pitchers with high slots and releases, and tend to be pretty good at helping arms sharpen their breaking balls. While Eyanson’s release traits aren’t quite as extreme as, say, Trey Yesavage, he’ll present hitters with an odd look and should be a very tough matchup for years to come. He projects as a no. 3 with realistic no. 2 upside, and should be ready by early 2027.

Enddy Azocar, OF

When evaluating Boston’s system, Azocar was my favorite player to watch, and I’m still mad at myself for chickening out and only putting a 45+ FV grade on him back in May. The 19-year-old has shaken off some early growing pains after a midseason promotion to High-A and is now hitting .279/.338/.547 in Greenville, good for a 117 wRC+. A plus athlete with projectable power and a long-term center field projection, we’ve bumped him to a 50 FV and slid him into the Top 100.

Azocar checks all of the “this is what they look like” boxes you want to see in a projectable position player. He’s high-waisted with broad hips and shoulders, sinewy with wiry strength already and a chance to fill out and develop plus power at maturity without sacrificing much speed. Early indicators this year suggested that he’d grown into additional power year over year, and as the season has progressed, it’s become clear that the 45 present power grade I gave him when our list ran is already hopelessly out of date, as his 90th-percentile exit velocity is over 107 mph and his top end is north of 113. That’s comfortably plus — it’s almost exactly in line with Jackson Chourio’s measurables — and, again, the kid is 19. He has a fast bat with a swing geared to lift pitches down in the zone, though with enough bat control to stay competitive on pitches upstairs.

The risk here is that Azocar’s approach won’t let the power play to its potential. He’s striking out a lot, a hair over 25% in High-A, with a sub-70% contact rate. He has a slight hitch at the start of his swing, but the problem is less mechanical and more related to his zone control and pitch recognition. He chases a lot in all counts and even more so with two strikes. Soft stuff in particular is a problem: Per Synergy, his whiff rate on breaking balls is above 30%, and it’s even worse on changeups and splits. He can hit them when they’re in the zone, which shows me that he’s capable of adjusting off the fastball, but he’s going to need to become more discerning, or better pitchers will carve him on pitches out of the zone.

The bet here is that there will always be some swing and miss in his game, but that he’ll hit enough to make up for it. He’s the age of a freshman in college, and it’s natural to think he’ll make at least modest improvements in his ability to identify and lay off breaking balls. If he’s able to do so, his upside is very high.

Kyson Witherspoon, RHP

In Witherspoon, the Orioles acquire another high-slot guy with a vertical attack and a plus breaking ball; Baltimore really does have a type. Witherspoon was Boston’s first pick in the 2025 draft, and he signed for $5 million after running over the SEC as a young junior at Oklahoma.

Witherspoon is off to an uneven start to his pro career. He’s turned in a few gems, but he’s not missing bats or throwing strikes like he did in school, and he’s posted just a 4.78 ERA and 4.87 FIP in High-A, underwhelming numbers for a player with his background and experience. One reason for that is that Witherspoon’s four-seamer has not played like an impact pitch. He’s sitting mid-90s and touching 98, as he was in school, but he’s lost four inches of vertical break year over year and the pitch is getting whacked: As of the All-Star break, hitters had notched a .428 xwOBA against it, and he’s understandably increased his usage of everything else significantly. His slider, curve, and cutter all look like average or better pitches, but it’s hard to see him sticking in the rotation over the long haul with a heater this vulnerable. Boston’s one of the best in the business at pitcher development, but perhaps a fresh group of coaches and analysts can help him find a path forward there.

As is, Witherspoon is on the starter/reliever line. He’s a good enough athlete, with some history of throwing strikes, to continue developing him as a starter for now. Eric and I projected him to the bullpen in our Red Sox list, though, where we think he’ll be better able to hide his fastball. Whether in short stints or a multi-inning role, we think he can be an impact arm in relief.

State of Baltimore’s System

While Eric and I were a little split on Baltimore’s system when we wrote their list in May, it’s clearly in good shape now. We have a 35+ FV grade or better on 72 guys, and even though some of those players will fall off the list when we next dive into the system as a whole, the depth here is remarkable. They’ve also got plenty of potential stars, including the newly arrived Eyanson and Azocar. In our Farm System Rankings, we have Baltimore’s as the fourth best in baseball, an eyelash behind the Dodgers and pretty close to Detroit. It’s a good group with which to move forward, and unlike the ghastly tank job the Orioles underwent on either side of the pandemic, this reset shouldn’t take too long to bear fruit. As Michael Baumann noted in his piece on the Rutschman of it all, despite these trades, they aren’t in terrible shape for 2027.

Still, it’s fair to wonder if this is the route the Orioles should have taken. It’s certainly disappointing to see the Gunnar Henderson/Adley Rutschman era end with such a whimper, a mere few years removed from a 100-win season and what looked to be an incredibly bright future. Fans will, rightly in my view, wonder whether they’re stuck on a treadmill in the AL East; an understandable follow up is to wonder whether Elias is the right man to lead Baltimore through the franchise’s next phase. These are difficult questions. In a vacuum, the Orioles are in a decent spot looking outward, with a fairly low payroll, a number of good big leaguers, and a very good farm system. But baseball isn’t played in a vacuum and these are tough days for the folks running the show in the Charm City.