This week, I go 1-on-1 with the Host of Brewers Daily, David Gasper, to get the Milwaukee perspective on the most impactful deal the Cardinals made at the deadline in 2026, sending away Dustin May and JoJo Romero for Alexander Frias and Josiah Ragsdale.
We talk about the Tarik Skubal impact on the move, the seemingly steep price paid for a pair of rental pitchers, and what the Cardinals are getting in their two new young outfielders with loud tools and promising upside. This abbreviated edition of the podcast will bring you a great alternative perspective and perhaps validate a lot of what has been said on this forum already: the Cardinals did well on deadline day.
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Jake Wood (00:23)
Welcome into the Viva El Birdos Podcast. My name is Jake Wood, and I write for VivaElBirdos.com. I am the host of the show, and I am typically joined by fellow co-hosts Gabe Simonds and Scott Plaza. Unfortunately, they were unable to join us tonight. If you enjoy this episode, please be sure to like and subscribe to our channel. We are available on YouTube, Spotify, Apple Podcasts, and all of your favorite audio streaming platforms.
The Cardinals made three deals at this year’s trade deadline. The most significant of the trio was sending starting pitcher Dustin May and relief pitcher JoJo Romero to the Milwaukee Brewers for double-A outfielder Josiah Ragsdale and low-A outfielder Alexander Frias. Here to help us break this deal down from the Milwaukee perspective. He is the host of the Brewers Daily Podcast and a credentialed member of the Milwaukee media. We’re wading into enemy waters with today’s guest. Welcome, David. Gasper.
Dave Gasper (01:30)
Thanks, Jake. Appreciate you having me. And you know, we get to kind of cross behind enemy lines here as we talk about this very surprising intra-division trade.
Jake Wood (01:42)
You know, they say it’s important to keep your friends close and your enemies closer, so I’m more than happy to have you here.
Dave Gasper (01:49)
Man, I’m more than happy to be here, for sure.
Jake Wood (01:51)
Before we jump into the deal, how long have you been covering Brewers baseball, and kinda give us a just a little bit of your backstory before we jump into the good stuff?
Dave Gasper (02:00)
Yeah, so I mean I’ve been writing about the team for about nine years now. Starting as a writer at Reviewing the Brew, eventually being the editor there for several years. And then, you know, working in local Milwaukee Sports Radio as well. And currently writing for Brew Crew Ball as part of SBnation. And then, of course, the Brewers Daily podcast through FanArch, which is also on YouTube and Spotify and Apple Podcasts and all those various audio platforms.
Jake Wood (02:34)
So let’s get right into it then, Dustin May and Jojo Romero for Alexander Freus and Josiah Ragsdale. How are your fellow Wisconsinites feeling about the deal executed between the NL Central rivals?
Dave Gasper (02:48)
They’re all feeling initially that the Brewers overpaid in this deal because, you know, being a, you know, small market team and you know having the success that this team has had through the farm system, I mean we are prospect huggers over here. Matt Arnold himself is generally a prospect hugger. So when two of our favorite essentially breakout prospects this year, Josiah Ragsdale and Alexander Frias, are both included in the same deal and going to a division rival. That one stings quite a bit because a lot of us over here had our sights set on Tarik Skubal, and you know, that was where the Brewers could go. Everyone’s coming up with packages for Skubal. And then ultimately, of course, he goes to the Dodgers. Where else would he go? And the Brewers have to pivot from there. And it’s like, okay, Dustin May kind of makes sense. You look at his profile, it’s like, okay, that seems like something the Brewers could work with and could enjoy. But the price that they paid to give up, I mean, that was very steep. You think there’s got to be some sort of inter-division tax on it. But the Brewers seem to want May. And you know, Ragsdale and Frias, I mean, those are certainly hurting us over here. I mean, the Cardinals did a great job to get those two pried away from the Brewers’ hands.
Jake Wood (04:07)
You know, you mentioned Tarik Skubal, and you know, from like a St. Louis perspective, this is gonna sound completely ass backwards, but like I wanted you guys to be the ones to land Tarik Skubal. I don’t think there’s anyone across baseball outside of Los Angeles that wanted to see Tarik Skubal, you know, in a Dodgers uniform and, you know, when you’re thinking about like the broader scope of baseball, right? And the potential of a lockout looming. And you think about, well, okay, so what other teams across the league can kind of build up to potentially, you know, lessen the blow leading into these labor negotiations that are seemingly centered around mostly, you know, the LA Dodgers and what they’re doing and their ruining of baseball and such, like if you could imagine a starting rotation with Tarik Skubal and MIZ and Kyle Harrison, like that I know it it gives you that that what if what what could have been Yeah, man, I
Dave Gasper (05:06)
Yeah. Gives you the goosebumps. Yeah.
Jake Wood (05:10)
Like, even from a Cardinals perspective, like I was rooting ’cause I wanted to see just how good that could be, as much as we’re all really sick of getting our asses kicked by the Brewers.
Dave Gasper (05:26)
Yeah, I mean, I think that’s one where, as much as you guys are sick of the Brewers beating you, I think everyone’s also sick of the Dodgers just running through everybody and everything and getting every single player that they want. And it’s just like, we’re just going to, you know, win the World Series, and now we’re gonna sign Kyle Tucker too and you know, give him sixty million dollars a year because why not? And it’s just it it’s insane what they’re doing over there and how they’re saying, like, we’re just smarter than everyone else, because it’s so smart to want to target Tarik Skubal. They are just absolute geniuses over there. No one else thought of that idea. But yeah, and then like you see all these national reporters come out blasting the Brewers for not trying enough, and it’s like, anyone can do this kind of deal. Why didn’t the Brewers try? Well, and then my friend Adam McCalvey of MLB.com puts out there basically what the Brewers’ offer was. And it’s like they’re putting in Luis Peña, another top 100 prospect, and then another fringe top 100 prospect. I mean, like that was a very, very strong offer that the Brewers gave.
Jake Wood (06:34)
Certainly.
Dave Gasper (06:35)
Now they were all hitters; that was the deal. The Tigers, if they wanted an MLB-ready pitcher that they could
Jake Wood (06:43)
Right.
Dave Gasper (06:43)
put in. Basically, they were targeting Logan Henderson. And the Brewers were like, we are not going to put Logan Henderson into this deal. I kind of wish they would have maybe thrown in, like, maybe a Robert Gasser, a Coleman Crowe, a Brandon Sprout, you know, one of those other guys that’s not Henderson. And maybe then you could have maybe been a bit closer, but the Brewers still put, I think, the stronger overall prospect package together. I mean, River Ryan’s 28 years old. Like Brady Smith is in like High-A with like a five-something ERA. Like the Brewers put together the better overall prospect package. You know, even though there wasn’t a pitcher in there, like that’s also where you can negotiate versus just calling
Jake Wood (07:25)
Right.
Dave Gasper (07:26)
The Dodgers and saying, Hey, let’s just get this done right away.
Jake Wood (07:29)
Right.
Dave Gasper (07:29)
And just ruin all of your leverage. So that whole thing just stinks to me. You know, how it went about. And like I wonder too, if maybe Alexander Frias was that third piece in that deal because Frias has been starting to populate on some of those top 100 lists.
Jake Wood (07:46)
Yeah.
Dave Gasper (07:47)
And you know, for him being kind of that fringe 100 guy and the fact that the Brewers ultimately did include him in a trade for a rental starting pitcher, that makes me wonder if he was potentially that third piece in that deal. And the Brewers were willing to move on from him, so you know that that’s where the Cardinals can kind of swoop in, being that pivot, as the Brewers had to pivot
Jake Wood (08:09)
Yeah.
Dave Gasper (08:10)
to Dustin May, and they end up getting one of those pieces that the Brewers were maybe thinking again- this is just pure speculation on my part that it’s him. But maybe one of those pieces that they were willing to include for Skubal, they end up sending to the Cardinals for May.
Jake Wood (08:26)
Yeah, and that’s there. There have been certain talking points as, you know, local St. Louis media has kind of talked about, you know, that’s kind of their read of the situation too, was that the Brewers were eyes set on Tarik Skubal, and whenever that didn’t happen, they were like, crap, you know, what’s what’s next? What’s plan B? And the Cardinals were just kind of sitting there like, Hey, you know, we’ve got Dustin May, you want you want a little piece of Dustin
Dave Gasper (08:52)
Yeah.
Jake Wood (08:52)
May? And Matt Arnold, like, you know, that doesn’t sound too bad. And so, like, jumped in that direction instead. And, you know, I can tell you that there were a lot, a lot of apprehensive Cardinals fans here in St. Louis, because it wasn’t until about like two o’clock Monday afternoon before this deal was consummated, and up until that point the Cardinals had done absolutely nothing, and so all of the fans were sitting here crying out, you know, Chaim, make a move, make a move, do something and our knight in shining armor, Matt Arnold, to the rescue.
Dave Gasper (09:26)
Yeah. Dude, it was the same kind of thing over here. I mean, like we like Brewers lose out on Tark Skubal. All they had done was get Bo Naylor from the Guardians and Cody Huer, who they ended up, you know, trading away. You know, like
Jake Wood (09:39)
Flipping. Yeah.
Dave Gasper (09:40)
They didn’t even want to keep Cody Huer. So all they ended up getting was Bo Naylor. And it’s like, Matt Arnold, are you gonna wake up? Are you gonna do something? You just let Skubal go. Like, like, come on. And so then it’s like, okay, yeah, you know, you get Dustin May and
It’s like, alright, hey, you know, there you go. I like him. He’s got a sinker. The Brewers love pitchers with sinkers. And then it’s like, you know, and then there was that time, ’cause there was still like an hour or so where we knew it was May and Romero. We did not know what the return was. And then when it comes
Jake Wood (10:09)
Yeah.
Dave Gasper (10:10)
out that it’s Ragsdale and Frias, everyone’s just like, no, what are we doing? Like
Jake Wood (10:14)
Ha ha ha ha.
Dave Gasper (10:16)
That is way too much. So yeah, that cost him a bit, and of course, like everyone begs him to do something and then he does something, and they’re like, Not that. Don’t do that. Trade prospects
Jake Wood (10:27)
Yeah.
Dave Gasper (10:28)
to get someone. Not THOSE prospects. Like it’s fun to see that play out.
Jake Wood (10:31)
Yeah. We want you to fleece somebody. Don’t give away the farm. Yeah. Well
Dave Gasper (10:36)
Yeah. Yeah. Yeah. Trade prospects. The prospects we hate. You know, like, don’t trade the good ones. Well Yeah. Yeah.
Jake Wood (10:41)
Yeah. Well, that’s that’s every fan base, so I mean what do you what do you expect?
But you know, I do, I wanna kinda turn our attention to Dustin May just a little bit because I do think that even though he’s not Tarik Skubal, the Brewers are still getting a guy who can be a number three in that rotation, assuming health. Because I don’t know what the Brewers can take from how the Cardinals handled him, but the Cardinals were able to get, you know, the most healthy, most effective version of Dustin May so far. And you know, i we this season we saw a return of the top-end stuff that he’s able to generate. And even I know this is not the most pleasant memory for us in different circumstances, but Dustin May no-hit the Brewers through the first seven innings in a start back at the end of May. And I have to think that that memory kind of stuck in the back of the mind of Brewer’s front office members whenever thinking, okay, maybe Dustin May might be, you know, he may not be the top of the rotation arm we were looking to pair with Miz, but he’s still gonna give us you know, really good quality you know, in the middle of our rotation instead. And then I also think it’s really interesting that JoJo Romero was included in this package as well. Because whenever I look at the Brewers’ bullpen, now you can tell me I haven’t been paying as close attention to the Brewers’ roster. I know they have Aaron Ashby at the back end of games, but I also thought they had D L Hall back there, which was another lefty. Is he still injured, or is he active and returned?
Dave Gasper (12:15)
He’s back now. He just came back. Yeah, he had like a peck issue like a month or so ago, like tightened up on him. But yeah, he just came back the other day, and you know didn’t go super well. Came in for the seventh inning and ended up giving up a two-run homer to Endy Rodriguez, I believe,
Jake Wood (12:33)
Mm.
Dave Gasper (12:33)
and then ended up getting yanked for Antonio Sanzatella, the other Brewers trade deadline edition. So yeah, but yeah, you got DL Hall there, you got Aaron Ashby, and then you have Uribe, Abner Uribe, and Trevor McGill kinda locking down the eighth and ninth innings. So yeah, it’s a good bullpen, but one that could use some reinforcements. They have ridden their horses pretty hard. Aaron Ashby’s been used a ton. You know, Grant Anderson’s kind of been used a ton. Eurebay’s been used a ton. So they could use kind of some fresh arms back there.
Jake Wood (13:09)
And the good news is that, you know, Jojo’s not on the IL because of an arm issue. His appendix literally burst. And that was
Dave Gasper (13:17)
Yep. Yeah.
Jake Wood (13:18)
Actually, the surprising thing here in St. Louis for most of us was the fact that JoJo’s appendix bursting was the single giant death nail to the Cardinals’ wildcard hopes, and the Cardinals really had nobody to fill that leverage lefty role
Dave Gasper (13:35)
Mm-hmm.
Jake Wood (13:35)
out of their pen, which right out of the break, they were blowing games left and right. And, you know, I do wanna say that surface level numbers, JoJo Romero is not all that like impressive, but whenever he comes into games, into high leverage situations, you can count on that dude as nails to get you important like high leverage, high stress outs ninety-five percent of the time. And and I think that Brewer fans are gonna come to really like seeing JoJo Romero come out of that bullpen down the stretch, and especially as you guys get into October and you’re facing Shohei Ohtani and Kyle Schwarber and Matt Olson potentially and all of those those big lefties that perhaps you know Pat Murphy is gonna wanna go to earlier in a high leverage situation early if a if a starter just doesn’t have it that night in the playoffs, I think that JoJo Romero could be a a a very unheralded piece, a part of this. But, you know, you referenced it before, but what are the Cardinals and their organization getting in an Alexander Frias and a Josiah Ragsdale? Obviously, you know, they aren’t the very tippy top of the Brewers farm, but, you know, they both still come very highly regarded from a very deep Brewers system.
Dave Gasper (14:53)
Yeah, I mean, Frias, I mean, he’s got as much upside as anyone really. I mean, he’s got the potential to put it all together to maybe be like, you know, a top ten, top twenty prospect in all of baseball. If he continues on the trajectory that he’s been on. I mean, he lit up the complex league. Hasn’t been maybe quite as dominant in Low A Wilson, but still incredible tools, incredible talent there with him, power, you know. Contact ability, good speed. So lots of great stuff there with Frias. A little bit further away, but I mean, a teenager with some incredible, you know, raw talent, raw upside. Josiah Ragsdale, I mean, really a breakout prospect. He was a seventh-round pick out of Boston College. And has just, you know, lit up the minor leagues this year. I mean, him and Andrew Fisher and Josh Adamshewski and all those guys down in Appleton and then Biloxi on Double-A. I mean, they have just been raking all season, putting up monster numbers. Ragsdale, I mean, he was not expected to be this good. I mean, he’s expected to be solid.
Jake Wood (15:58)
Yeah.
Dave Gasper (16:00)
The power wasn’t necessarily expected to be there that much. But I mean, he’s got like a 20-20-30 season now, like 20 doubles, 20 homers, 30 steals, something like that. So, like the power has really kind of shown up quite a bit. The steals are there. But also you gotta watch out for that strikeout rate. I mean, even with his home runs and his success there in Double-A. The strikeout rate of near thirty percent with Double-A Biloxi. So, you know, there might be some question as to whether or not he’s gonna be able to make enough contact as he goes up the chain. But still a very talented player. You know, I think at the very least a pretty high floor of a fourth outfielder.
Jake Wood (16:38)
Yeah, that seems to be what the Cardinals’ new brain trust is targeting, especially, you know, specifically in like a Josiah Ragsdale, you know, their Double-A hitting coach, had talked to one of the St. Louis reporters and talked about how, you know, this this new front office, this new regime is looking for hitters who who pull the ball in the air, who can lift and separate to their pull side. And, you know, by all accounts, that’s something that Josiah Ragsdale and the Brewers development team kind of unlocked for him in that set that next level of his development. And I think that’s kind of what made him so appealing to the Cardinals as they’re kind of shifting their mindset and their approach to more of what the Brewers tend to feature, not so much from the offensive side, but from the pitching side. Guys with big stuff, guys that play, you know, at the top of the zone and can just overpower their opponents essentially, and then, you know, from an offensive sp perspective, big exit velocity, big tools, lots of moldable clay, if you will.
David, real quickly, where can fans find you on your socials? And can you give a quick plug to your show?
Dave Gasper (17:46)
Yeah, you can find me on X or Twitter, however you want to call it still, at @DGasper24. Got lots of content like you know from the clubhouse, covering the team out there. And then the show is Brewers Daily. It is on YouTube, Spotify, Apple Podcasts, all those places. Just search Brewers Daily, and you’ll find it. So yeah, it’s plenty of places. And then you know, where I do all my writing is at brewcrewball.com.
Jake Wood (18:16)
And for Cardinals fans, David’s show is very similar to what we have here in St. Louis, and B-Schaeff Daily, Brendan Schaefer, who’s the writer for MLB.com locally. So it’s very similar to what his he’s is, and if you want to keep up to date on, you know, some of the Cardinals’ near-division foes, David does excellent work. You can stay as informed as you possibly could want to be following the Brewers. It’s been a wonderful follow for me ever since David and I kind of connected a few years ago before Viva El Birdos, back whenever it was still Rambling Redbirds and that whole spiel kind of
Dave Gasper (18:52)
yeah.
Jake Wood (18:53)
was my own mind creation. But I’m so glad to finally have been able to get you on the show and be able to talk to you. David, thank you so much for your time today. We sincerely appreciate it. Hopefully we can catch up after the season and a deep Milwaukee postseason run and do kind of a post-mortem on the NL Central.
Dave Gasper (19:12)
Yeah, absolutely appreciate it, man. Appreciate you having me on, and yeah, glad we were finally able to get something on the schedule and get something done here. So this was a lot of fun, happy to do it.
Jake Wood (19:22)
Absolutely. Thank you so much. And thank YOU so much for joining us for this episode of the Viva El Birdos Podcast. Don’t forget to rate, review, and hit that subscribe button so that you’re notified every Monday morning. For my fellow writers, Gabe Simonds and Scott Plaza, who were not with us physically tonight, but in spirit, my name is Jake Wood, and we’ll talk to you all next week and bring you more great Cardinals content. Have a great day, St. Louis, and let’s go Cards!