The long and winding road of October led us exactly where the regular season standings would’ve hinted: The best team in the National League facing off against the best team in the American League.

In a matchup of two lesser-known rosters that have each played near-flawless baseball over a seven-month stretch, the Milwaukee Brewers play host to the Tampa Bay Rays for Game 1 of the World Series tomorrow at American Family Field. And somehow, we found a few minutes to pull Talkin’ Jake away from his podcast mic to preview it all for us in this week’s newsletter.

How did we get here? Who’s the breakout guy? Who lifts the trophy? Jake has it all for you right down there 👇

JAKE: I would say I believed in the Rays. On our Talkin’ Baseball prediction episode, I picked the Rays to go to the World Series. They were the best team in the American League going back to, like, June 1st, kind of undisputedly. I think they would have gotten more praise, but sadly, the AL was so weak this year that they didn't get their flowers. Because they essentially did the same thing as the Brewers, that the Brewers did it against the National League — which was one of the best divisions we think we've seen. Some of the teams that got left out are kind of crazy.

So, I guess when it comes to the Rays — they used to be the standard of small markets. I don't know if it was personnel. I don't know if strategy changed. But for a few years recently they got away from defense. Whenever the Yankees used to play the Rays, you almost had to get ready for a level of frustration, because you knew they were going to make frustrating highlight defensive plays that were gonna feel brutal. So I think they've gotten back to that.

And you know what's funny? You said Yanks division rival making it to the World Series. That's happened the last two.

JAKE: Well, the thing that gets overlooked with both these teams is they pitch. Everyone pitches. The final four teams remaining were arguably the four best pitching franchises. If you were a pitcher free agent and you wanted to get better, which teams would you want to go to? It's probably Rays, Guardians, Dodgers, Brewers. 

That's the funny part. We've been breaking down these series for Talkin’ Baseball, or even just did Wake n Jake. You talk about, "Oh, how impactful would this guy be?" And it's like, well, every dude who touches the mound has a chance to be nasty. So it starts there. Both these teams have that base.

For the Brewers, I think they believed a hole in the market was just getting good baseball players, which sounds remarkably ridiculous. But if you look at it, I mean, Sal Frelick is not a big guy. Brice Turang, not the biggest of guys. Luis Lara, not the biggest guy. A lot of teams were chasing, whether it's exit velo, or … Don't get me wrong, I love freaks in sports, but it's also just being good at something. I think everyone knows a buddy that, if you were gonna play bar games, it could be anything, foosball, bags, darts, you just know your buddy. You're like, "Oh my god, they're good at it." It felt like the Brewers got those guys that were good at baseball. But they weren't measuring out great analytically. That's just what the Brewers do. 

And they believe in the sport. It's almost like they dug up an old historical baseball thing. Like, "This is what baseball used to be!” And they were like, you know what? Let's try to live by these rules and see what happens. And it still works! They've got a tough manager. They play situational baseball. They run well. You can't get on their field defensively if you're not plus. 

And so many other teams have done, like, "Well, I think this guy can hit, so let's put him out there and we'll figure it out." No! That used to be the requirement to make it to the big leagues. The box you had to check is, “what position do they play?” There's guys where you look at their minor league stats and it's like, "Well, he looked like a pretty good hitter, but didn't have a position." In baseball, they thought the cheat code was getting that guy to play any position. Turns out the cheat code is playing good defense, and then you need to do more after that. But that's how they've broken the game: By playing good baseball.

JAKE: So, a couple things you need to know. I am a baseball nerd, so as much as I throw that around in a seemingly rude way, I also say it in a complimentary way to a lot of front offices. I've known of Jake Bauers since he was a prospect, because he was a legit prospect. He came up with the Rays very briefly, that's part of the World Series storyline.

But yeah, when I was playing my loser video games in 2016, 2017, 2018, I knew who Jake Bauers was. I knew he was a first base/corner outfielder. I knew he had a chance to be a really good hitter. But like a lot of prospects — and one of my favorite weird hobbies is bringing up top prospect lists from 2020 and looking at the top 100, and you'll be shocked, because there's no rhythm or rhyme to it — the game has a way. 

When he was a Yankee, Jake Bauers had some good at-bats, and he was basically a platoon player. Didn't feel like he had a position. I think he was just in a weird spot where his adding value of being able to play first base and the corner outfield didn't allow him to be a high-level one at either. From what I've seen from him playing first base, I've been very impressed.

And then the at-bats. I obviously didn't think Jake Bauers was gonna be second in the NL in on-base percentage this year. But if you tie his NLCS to his 2026 performance, look at the year he had. He had a great year, so I wasn't surprised he balled out in the NLCS. I'm more surprised by the full season he had, and I think the Bauers family might tell you that as well.

JAKE: If you like sports, it is a high-level version of the sport, and a version of the sport that we didn't know if we were ever gonna see again. As a company, one of our mantras is a homer isn't a great highlight, but a diving catch is. An amazing outfield relay is an amazing highlight, but a home run isn't. I think the plays that make you watch baseball and be like HOOOOO. Defensively, base running, situationally, these teams have that. That's going to be a lot of fun.

If you like high-level pitching, you're gonna be blown away. Man, the pitching is so good. So if you like an NFL game to be 51-49, then this series probably isn't for you. Hopefully, by the end, it starts to loosen up a little bit. When guys have seen relievers and the offense takes a spike. But the pitching's so good.

JAKE: So, free ad for Wake n Jake, and free ad for Bradford Doolittle, because I honestly took a lot of his article and used it in Wake n Jake. I think the tangible takeaways that teams will look at in a copycat respect is that both of these teams, with runners in scoring position, make an emphasis to just make contact. Which, again, if you're a baseball fan who only played in Little League and you're coming back now, you're like, "Oh, that changed?" These two teams had the two lowest launch angles with runners in scoring position. So they're literally just trying to put the ball in play. Our sport came so far away from that, which is jarring.

But I think that's going to be one of the biggest takeaways. I think we're still three or four years removed from a thought process of, like, "Hey, get your good swing off, because you don't know that 0-2 pitch might be the hanging breaking ball." The game has feel in situations that you need different swings, and sometimes you're still going to hit a home run. But you can't go up with the thought process of it, because it's the hardest thing to do in sports. 

So I think having players with multiple swings, different approaches with runners on, and then I think general athleticism. I just think it's so hard if you don't have the pressure that speed puts on teams, and if you lack defense, it will be exposed.

JAKE: Ooh, that's a fun one, huh? I have one hot take that's so boring it hurts: Kevin Cash.

I currently have this as a 60 percent chance Milwaukee wins, so that's why I preface it as my hot take. Kevin Cash has an argument for best manager in the sport. I also think there's an argument that he's just a really good manager. If I ask you, what do you know Kevin Cash for? It's one bullpen decision that was made by a binder. I think he's a good manager. There's a chance, and I hate this, because I'm rooting Milwaukee. But there's a chance Kevin Cash puts on a managerial show, in a way that would do something for me, because this analytical cycle of things that went away that are now coming back — analytics told us managers don’t matter. These two managers manage. Managing might matter!

But let me give a player too. How about Jackson Chourio. They won the World Baseball Classic. He's 22, and if you bring up Baseball Reference, he's the first guy to do this, this, and this before a certain age. But with a World Series ring and those stats, it goes from the list being like, "It’s Chourio, A-Rod, Bonds, and Frank Sinatra"  to just being like, "The only player to be 23 and younger and do this, this, and this, and have a World Series ring is Jackson Chourio."

JAKE: I am going Milwaukee in six. I think they are the better team. I think the Rays will run out of bullpen arms. I think the Brewers almost have five or six relievers that could dominate a seven-game set. And that's not how it works — three of them will be bad, but that still means you have three guys who are nasty. The Rays have Baker. They have a couple options after that. But one or two of those is going to be bad. I think it's tough for me to picture this series being short. I think by the end, I could see the Rays running out of arms, and the Brewers at home, Game 6 in Milwaukee. Scenes.

JAKE: I'm going to give this question immense thought. I think for live streams, you need energy. You need love for baseball. And you also need, like, a silly, weird side to get through a game.

My first pick is Tyler Glasnow. Awesome dude. There'd be funny clips of just him being tall and me being short. And there'd be squirrely conversations. There'd also be, like, heavy baseball. 

And then I would go Jeter, just because, like… have to, right? Like, me and Glasnow would have some moments, like, “it’s Derek Jeter!”  If he's in, like, it almost turns into me and Glasnow playing a game of chicken. Like, who can get Jeter to break first?

Simple. Who’s winning it all?

The best of what came out of Jomboy HQ, the Warehouse, and anywhere else we wandered out to over the last week.