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Thoughts on the World Series

By Gabe Simonds Oct 22, 2026 | 8:30 AM
MILWAUKEE, WISCONSIN – OCTOBER 12: Dustin May #21 of the Milwaukee Brewers reacts in the fifth inning against the Los Angeles Dodgers in game two of the National League Championship Series at American Family Field on October 12, 2026 in Milwaukee, Wisconsin. (Photo by Patrick McDermott/Getty Images) | Getty Images

The temptation was too great. I had to do it. I thought of the idea of writing a point-counterpoint on who to root for in this World Series first. I was going to make a sincere effort to make an argument for both teams. I came up with my headline. And then I realized no matter how good of an argument I came up with, I would end up saying root for the Rays, and most Cardinals fans would say that, and I thought that stating the obvious right off the bat would be fun. And then I physically could not bring myself to write more. I tried to enter a bunch of spaces to fool you into thinking that was all I wrote, but that wouldn’t hit the same. So there you have it. Hopefully that is still up when you read this (I’m posting this 30 minutes later)

The Brewers and Rays matchup appears to be breaking people’s brains, because I have somehow seen multiple people earnestly claim this is a win for the anti-analytics crowd. Analytics does not mean strikeouts people! It’s using data to gain the upper hand. These are possibly the two greatest organizations at doing that. Just because they have some old school players does not make this matchup into one of two teams facing off who spurn analytics.

In theory, if we ignore the divisional component of this matchup….there’s really no reason to root for one over the other. They have very similar arguments. Low payroll, small market, very well-run for years, no championships ever, best team in their league, plays fun baseball, like as alluded to above, even old school fans will like both teams. If the Brewers were in the NL East, I’d have a very difficult time picking one.

Why the Brewers

  • If I’m being completely honest….. Milwaukee the city deserves a championship way, way, way, way, way, way more than Tampa Bay. As an anti-teams moving fan, Tampa Bay should frankly move. They don’t get any support at all and they’ve been good for years. Like half of Florida roots for other teams, because they didn’t grow up in Florida. I won’t be rooting for the Brewers for reasons you’ll see later, but like this is a very tempting reason! It’s why I won’t be mad if they win.
  • Tampa has this reason too but…. it’s time. I did not root for the White Sox, because I felt like them winning it this year would be jumping ahead of the line. Their organization has not been run well enough to deserve a ring. They weren’t good enough this year to deserve a ring. On the flip side, Milwaukee has certainly had one coming. Their collective play the past 10 or so years should have a ring at some point. It’s like how the Cardinals deserved a ring in 2006 even though the 2006 Cardinals did not. The organization deserved it. Just like the Brewers.
  • They were the best team. Frankly, best regular season team who isn’t a big market who has never won is a much easier rooting interest than we ever get in the World Series. Of course literally of those things apply to the Rays.
  • The National League was light years ahead of the American League and the championship should probably go to an NL team to accurately represent the 2026 season.

Why the Rays

  • Here’s my number #1 schadenfreude reason: for the purposes of the rivalry, we kind of need them to not win so that the trade can become the next Lou Brock trade. Which really isn’t a good comparison because in that time period, players didn’t have free agency and both players the Cardinals gave the Brewers will be free agents (that they won’t resign). JoJo Romero has been about as good as advertised, Dustin May has not. The Brewers winning the World Series means they won’t give a shit if Josiah Ragsdale wins two MVPs for the Cardinals. Them not winning the World Series? Kind of feel like it’d be their Marcell Ozuna trade. I don’t have a problem with the Brewers and yet this evil fan in me can’t help but root for this outcome.
  • It’s time. The Rays have been a well-run organization for much longer than the Brewers have and the Brewers have been well-run for a pretty long time at this point! On top of that, they’ve already lost two World Series in the past 20 years. They’ve gotten right on the brink, tasted it and lost. By this made-up metric, they deserve it more than the Brewers.
  • They were the best team. I am a weird neutral fan in the playoffs. Because I have a hyper-specific set of criteria for who I want to win if it’s not the Cardinals and somehow both the Brewers and Rays qualify. If it’s a team who has won too much, I don’t want them to win. If it’s a team I don’t feel like is very good, I don’t want them to win. So they have to be a great team, but not a perennial great team, and oh yeah it can’t be a team I already hate (I have never liked this modern version of the Phillies, and while I want to blame it on 2022, that’s not why. I don’t have a good reason. I have never wanted them to win the championship for reasons I’m not totally clear on. It’s not even the fans. At least not specifically.)
  • This Timeless Ticket scandal is very bad vibes for the Brewers. If you don’t know the story, 10 years ago, fans could buy a “Timeless Ticket” and they bought it for $1,000. I believe they got to go to a certain number of regular season games, but also could use this ticket to get the “best available” at any playoff game. Well the “best available” was not exactly what they were offered, but a 400 level seat. Well it was deemed best available by the organization.
  • By that some token, Brewers owner Mark Attanasio was interviewed recently asking why baseball needed a salary cap when baseball is in a great place and two teams like this are in the World Series. I know a lot of you are for the cap, but that’s not why I’m listing this here. He said “it’s been 44 years, and there’s a sense in the community that it could be another 44 years” and whether nor not you agree with the cap, I think this is a very stupid thing to say on the eve of playing a World Series. There had to be a better way to make this argument.

But really, it’s mostly the trade. I want that to be a sore spot for Brewers fans for years to come.

Could Cardinals have gotten this player?

Alright, let’s play a game. I’m going to highlight some players, and then show how they were acquired by that team. In theory, at that time, could the Cardinals have gotten that player instead? What would it have taken? Some of these will require incredible hindsight, I’m guessing most will.

Christian Yelich – I would imagine so if the Cardinals had more patience. Yelich wasn’t available at the time the Cardinals traded for Marcell Ozuna. In theory anyway. But instead of trading for the guy coming off a career year, let someone else trade for him, and wait for Yelich to become available. Does require a little bit of hindsight I suppose because Yelich being available wasn’t a sure thing. I don’t know if the Cardinals would be willing to pay the price either. Despite the return for him not doing anything, they were in fact great prospects at the time. Ironically Zac Gallen and Sandy Alcantara might not have been good enough prospects for Yelich. This would be a very interesting alternate reality.

Brice Turang – drafted two picks after Nolan Gorman so yeah. And I’m bringing him up specifically because he was also drafted out of high school. But from the draft stuff I read about Turang…. he sounded dangerously like Pete Kozma. Didn’t work out that way of course. But if you removed the names, and then in the upcoming draft, had to pick between Turang’s profile and Gorman’s…. most of us are falling for Gorman again.

William Contreras – I mean it would have been nice to have been gifted him for essentially for free because the Braves decided they didn’t want Contreras anymore when they got Sean Murphy. Everyone knew the Cardinals needed a catcher. I doubt the Cardinals were interested because Contreras’ defense was not good at the time – the Brewers cleaned it up, although after that initial season, I hadn’t realized he’s basically an average defender. But still that’s way better than he was with the Braves. Cardinals could have been that third team I’m pretty sure.

Joey Ortiz – Realistically, I don’t think so. He was in the Corbin Burnes trade. The Cardinals didn’t have a Corbin Burnes after the 2023 season.

Trevor Megill – Yes definitely. The Cardinals go after a bunch of guys like this, most don’t turn into him. Terrible with the Cubs in 2021, claimed off waivers by the Twins, he was pretty solid, but had a not very good ERA. Didn’t make Opening Day roster in 2023, was absoltuely terrible in AAA, Twins gave him to the Brewers at the end of April for a PTBNL who hasn’t made the majors and they unlocked the elite reliever in him. But the process of getting him is not really any different than the Cardinals getting George Soriano.

Yandy Diaz – I guess, though he was part of a really strange deal. He was in a three-team trade with the Guardians and Mariners. The Rays didn’t believe in Jake Bauers – on the Brewers now funny enough – so they traded him to Cleveland. In return they got Cole Sulser and Diaz. Cleveland also got Carlos Santana and traded Edwin Encarnacion and a draft pick to the Mariners. Diaz was 27 at the time with no position and had a grand total of 120 PAs as a good hitter. He would not have stopped the Cardinals from getting Paul Goldschmidt and probably not Nolan Arenado either since he wasn’t a good defender at 3B. I’m not sure he lasts that long on the Cardinals even if they do trade for him given those two facts and that he wasn’t great in 2021.

Junior Caminero – Here’s another one involving the same types of teams. Caminero was traded for Tobias Myers, who was 22 and on the verge of the majors – except Cleveland sold Myers before he ever made the majors. Caminero was coming off his DSL season, so this is your Yordan Alvarez trade. Myers ended up on the Brewers and was traded with Freddy Peralta to the Mets. Peralta is now with the Rays.

Victor Mesa Jr. – I imagine so. He came into the season as the 44th ranked prospect in the Rays system by Fangraphs. He was traded for a DSL prospect. One not ranked particularly high in the Marlins system.

Bryan Baker – Yes, he was traded for a draft pick last deadline. Not sure it would have been well-received considering he was a 30-year-old mediocre reliever (or so it seemed) at the time, but yeah the Cardinals could have done it.

I mean yeah pretty much anybody in the bullpen could have been acquired, cheap teams acquire their bullpen cheaply.

Other interesting note: Ace Drew Rasmussen for the Rays was part of the return for shortstop Willy Adames. I mentioned Bauers originally came up as a Ray.

Former Cardinals section

Brewers – Dustin May, JoJo Romero – the aforementioned trade that is making me root against the Brewers

Rays – Richie Palacios, Ryan Vilade, Steven Matz – Palacios for Andrew Kittredge, Vilade was a waiver claim, and Matz was a free agent.