A long time ago, I was listening to an interview with legendary poker professional Phil Ivey and the interviewer asked the question (paraphrasing) How would you recommend a player learning the game get better the fastest? Phil said something to the effect of (paraphrasing) Buy in to a game at much lower stakes than you would normally play, and then play every single hand for an hour. Try and figure out how you would play all of these different hands in different situations and positions that you are normally taught not to play in. In the spirit of that recommendation from an all-time great, Chorizy and I are once again going to undertake the exercise of making a White Sox trade with every team in the majors…..this is the NL Central Edition.
The Au Jus
Chicago Cubs
White Sox send: Mike Tauchman of; Christian Oppor lhp
White Sox receive: Kevin Alcantara of
Rationale: Kevin Alcantara was a top 100 prospect heading into the 2025 season, nearly across the board. The combination of defensive profile (plays cf) and size (6’6″) with power potential was incredibly appetizing. Unfortunately 2025 came along and his play in AAA was pedestrian. The power never fully showed up (17 HR in 430 plate appearances) the K-Rate stayed high as ever (29.8%) and the speed didn’t materialize either (only 10 stolen bases). A disappointing season overall. Now with Kevin only being 23 years old normally you’d just say, okay kid, go git em again in AAA next season.
Unfortunately, my mans it OUT OF OPTIONS. That’s right, he’s gotta stay on the major league team in 2026 or risk being exposed to waivers, which the Cubs aren’t going to do because he’s too valuable. Conversely, the Cubs were a game away from the NLCS last year with a roster ready to run it back and compete again, so they can’t really just hide this on the 26 man and hope for the best. Alcantara needs playing time that the Cubs really can’t guarantee him. I’ve never seen a more obvious trade candidate. Given that scenario, this was so fucking hard to value. Alcantara isn’t a top 100 prospect anymore, but he’s locks as a top 200 prospect, so pretty damn valuable, but on a team with zero leverage. So this is the deal I constructed. It’s possible a team in a similar position to the White Sox that can guarantee him the playing time and eat shit in the process if he sucks will pay more, who knows.
Mike Tauchman was non-tender a year ago for the Cubs, the White Sox scooped him up and he had a very nice year. It’s funny that with Kyle Tucker not likely to be re-signed and Seiya Suzuki effectively a DH this year, Tauchman would once again have utility as a part time right fielder / bench bat on this Cubs team.
The real treasure of the deal is Oppor. He’s a young lefty with good size and velocity and he torched A-ball last year. 32% K-Rate and a .198 batting average against. He’s raw, but his upside is as strong as Alcantara’s. Scared money don’t make money.
St. Louis Cardinals
White Sox send: Bryan Ramos 3B, Peyton Pallette RHP
White Sox receive: JoJo Romero LHP
Rationale: As a team in the midst of a rebuild, it’s difficult to find trades with a team that is likely going into a rebuild and is likely doing it a year too late. But we press on. The big names like Sonny Gray, Willson Contreras, and Nolan Arenado have no trade clauses that will definitely keep them from coming here.
So let’s take the outlook that the White Sox want to be in that mediocre mix at the mid-point of the season, deciding if they want to contend or sell.
JoJo Romero is an interesting target as he’s in his last year of arbitration (~$4M) and a solid high leverage lefty option that helps any bullpen. But not quite a closer. He’ll be a guy a lot of teams look at to bolster their pens as they go into the season. Assuming he’s his normal self, he helps the Sox or they trade him at the deadline.
In return, our sweet prince Bryan Ramos finds a home where he can break onto the field as they gut the team. Nolan Arenado’s shoes are some big ones to fill, but it helps the Cards not start the clock on a few guys and gives them a chance to see what Ramos is. Peyton Pallette didn’t do enough this year to reach the majors, but he’s likely close after notching 11 saves across AA and AAA. Assuming the Cards want to turn it over fast and they have the money to do it, giving them guys that can play right away might be appealing.
Cincinnati Reds
White Sox send: Andrew Benintendi LF/DH + $16M
White Sox receive: Carlos Jorge CF
Rationale: It’s difficult to find a park adjustment that goes in your favor when the player currently plays for the White Sox. But Beni’s park adjusted HRs go from 20 to 29 when putting him in Cincy. That’s not a perfect number, but it is a notable one. The other notable number is that he’s owed $32M over the next 2 years. That’s pretty steep for the Reds, so money will change hands to make this happen. Thank you Big Daddy Ishbia.
The return is a centerfield prospect in Carlos Jorge that has sputtered at the plate as he got to High A. The glove seems to play in CF though, after a move from second base. His distance from the majors and his inability to produce power so far make him available in this type of trade. What intrigues me is that with the glove comes a guy who reached base 34% of the time this year, but with that stole 40 bases.
This is a salary dump plus opening up a spot in the outfield for some young players. I’d expect a heavy dose of Brooks Baldwin if the Sox can get this done.
Pittsburgh Pirates
White Sox send: Billy Carlson ss, Javier Mogollon 2b & Wilfred Veras of
White Sox receive: Oneil Cruz of
Rationale: Much like Leonardo DiCaprio’s preferences in dates, Oneil Cruz is getting a little long in the tooth to still be on this Pirates roster. At 27 now and finally reaching arbitration, when things can start getting expensive, it’s time for the thrifty Bob Nutting to impose his will. Cruz has had an injured year, a breakout year and then a fallback year. He has permanently changed positions, from an erratic (read bad) shortstop to a competent everyday centerfielder. The tools are still off the fucking charts and so are the strikeout rates. If it doesn’t end up truly clicking, he’ll still be about the most exciting below average player on any roster. However, there’s scary upside here if the Ryan Fuller Band can impose their will on his swing decisions and contact rate. A potential superstar (I’m sorry, I know you have heard that enough).
Billy Carlson is the White Sox most recent first round pick. The word on the street is he’s a major league shortstop today, with the mlb quality bat tbd. Already a top 100 prospect depending on where you look and the easy main piece to the deal. I know the Pirates have Konnor Griffin, but the magic 8ball is pointing him towards centerfield in the majors, so this works great.
Javier Mogollon is probably the most fun prospect in the White Sox system. He’s listed at 5’8″ (not a chance he’s that tall) and he hits piss missiles ($1 White Sox Dave) on the regular. Probably a 2b, but the bat is the tool, should he develop a game plan at the plate.
I feel bad for Wilfred Veras, things were starting to click in the back half of 2024 and then it all just stalled out. It’s still huge power, but strikeouts are absolutely killing him (30% rate in AA last year). At still only 22 years old, he’s fallen out of the White Sox top prospect group, but still plenty of time to find it and have hisself a career, this would be a rebound shot in a new system.
Milwaukee Brewers
White Sox send: Korey Lee C
White Sox receive: Tyler Black 1B?
Rationale: I assumed going into this that Jeferson Quero‘s time had come and he’d be the 2nd catcher in the Good Land this year, but I see multiple blogs and the Athletic noting the need for a backup catcher. Well that’s just fine with me as we have a very serviceable one without a spot and without options. So the Sox send Korey Lee who additionally gives a little pop to the Brewers lineup.
In return, the White Sox get a player with a Fangraphs write up that might as well say “nobody knows what to do with this guy”. And he sounds exactly like a player Sox fans would fall in love with.
“Black has a keen eye, he plays with lots of effort, and he swings hard for a small-ish guy.“
Sounds super grindy. But also, they cannot find a position for this guy. He’s only missing reps at SS and C to have played every position in the minors. It seems like they’re settling in on 1B, but my man is 5’10”. Let’s not do that. Give him some run in the outfield and see if the bat is real.
