White Sox “Trades” with EVERY TEAM | NL Central Edition | 2027
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: Pierce George rhp; Mathias LaCombe rhp
White Sox receive: Kevin Alcantara of
Rationale: It feels like almost every year in this space, I attempt to trade for Kevin Alcantara, I like his upside! Every year Cubs fans dog me and tell me that the Cubs would never trade him for whatever price I name. Then the Cubs don’t really play him on the major league team and burn options like I burn greenbacks in the Video Poker machine. Now the rubber is meeting the road. Alcantara is out of options. The Cubs do suddenly have an open spot in both Right and Left field, but with Matt Shaw needed to probably learn one of those spots to make good on his first round pedigree, and the Cubs neighbors to the north laying waste to the majors on an epic run to their first World Series title, I don’t think the focus at Clark and Addison can afford to give the now 27 year old Alcantara as much run as he might need.
Enter the White Sox, who pretty obviously love #OutfieldChaos and realistically have two outfield spots very much unsettled. Years ago I think I offered a competent MLB player in this spot like Yoan Moncada….but now, out of options, I think a couple of minor league fliers is a more realistic price. Pierce George and Matthias LaCombe are both relief pitching prospects, with really fun tools. Neither needs Rule 5 protection until after next season and both, if things broke right, like George’s elbow (he’ll be fine) could end up in a Cubs bullpen in need to sufficient depth.
St. Louis Cardinals
White Sox send: Tanner McDougal RHP, Pierce George RHP, George Wolkow OF
White Sox receive: Ivan Herrera C? DH
Rationale: We here at FromThe108 are all about making dreams come true. And we have an opportunity to make Will Venable‘s dream of rostering 3 catchers a reality. Herrera is not great behind the plate, but at the plate, he’s gonna get on base about 35-40% of the time and he’s gonna get you around 20 HR. He had 19 the past two years.
The Cards also have a bunch of catchers, so they’d be trading from a position of strength. However, they don’t need to get rid of Herrera as he can simply DH. That would likely be his role with the White Sox most days, though it might be worth teaching him a little 1B. So you’d add a right handed bat with solid power, on-base skills, and not the huge strikeout percentages common with your left handed power. It also gives Will a little more pinch hitting flexibility late in the game.
Now, for the return. As I mentioned, the Cards don’t have to move him, but they certainly could. And I’m not the only one who noticed:
https://sports.yahoo.com/articles/red-sox-3-1-trade-231136516.html
Cardinals Receive: INF Henry Godbout (Boston’s No. 6 prospect), RHP Blake Wehunt (Boston’s No. 16 prospect), RHP Kutter Crawford
Cardinals Receive: RHP Carlos Lagrange (Yankees’ No. 3 prospect), RHP Thatcher Hurd (Yankees’ No. 6 prospect), LHP Kyle Carr (Yankees’ No. 12 prospect) and INF Ryan McMahon.
Note: This is for Herrera and Pedro Pages
I also saw one for Steven Kwan, but the combo of the URL and the format of the page made me wonder if I stumbled onto the dark web, so no link to that. But the point is clear, it ain’t cheap. So we gotta bring something good to make this dream a reality.
Tanner McDougal is somehow the shortest dude in this group. Both McDougal and George can absolutely bring the heat. Even if McDougal is ultimately a reliever (I don’t think that’s the case), you still get 2 guys that can touch triple digits and are just about major league ready. The upside version is Tanner is a starting pitcher that throws absolute gas and Pierce is a high leverage guy. That’s a nice return, but it’s not enough.
George Wolkow cranked 22 HRs and drove in 100 runs in Winston-Salem this year. A real power bat that will be able to take his first legal drink in about 2 months. He’s still a ways away from the majors, but the power is real and he’s a giant. And as a hometown kid, I think a lot of people would be sad to see him moved, but that’s part of the process…
Cincinnati Reds
White Sox send: Shane Smith RHP, Edgar Quero C
White Sox receive: Nick Lodolo LHP
Rationale: I initially wanted to trade for Hunter Greene and send Andrew Benintendi back as part of the package to swap the unused $15M for Greene this year while he’s out and send Beni home to Cincy, but I couldn’t make it work. And I couldn’t see the Sox needing Greene for only his TJ rehab year and then 1 season.
So I pivoted to a starting pitcher on an expiring contract: Nick Lodolo. Nick looked very good in 2025, but in 2026 battling blisters, he only pitched 108 innings with let’s say lesser results:
The Reds won’t exactly be selling high here, but Lodolo is an established starting pitcher. He unfortunately dealt with a similar situation as Davis Martin. The can be the Super Blister Bros on our staff. But honestly, we’d wanna bring in Peter Cetera to teach them both how to play bass and callous up those digits. When healthy, Lodolo would have a very positive impact on this team and I think he’s worth the risk, much like Shane McClanahan but with less upside imo.
The return would not be that steep, but it would be some known guys who had down years. Edgar Quero is a nice fit here as the Reds will likely lose Tyler Stephenson in free agency. While Quero didn’t have a good year with the White Sox last year, he’s still quite young as he’ll be 24 in April (hopefully the start of the season). Shane Smith similarly did not have a good 2026, but he’s one year removed from being an all-star and he’s controllable for years.
The Reds likely have their eyes set on seasons past 2027 as the Brewers and Cubs are beasts, Hunter Greene is out for the season, and most of their players are controllable for a while. Lodolo doesn’t fit that mold, so he feels like the odd man out. The Reds can also wait until the deadline and see if improved results can bring back better prospects, but that has its own downsides.
Pittsburgh Pirates
White Sox send: Drew Romo c
White Sox receive: Jhostynxon Garcia of
Rationale: Last year in these pages I was much more excited for “The Password” than I am today. He finally made his major league debut, was horrible and was relegated back to the minors. There’s big tools here and big chase as well. In a regime that is trying to expand their outfield depth him and his one remaining minor league option feel like a gamble worth taking. In return the Pirates (who are basically tryna compete now) receive Drew Romo.
Romo wasn’t loved by fans, but his teammates and pitchers sure loved him. A guy that’s probably got a 10 year career as catcher #2 on teams was thrust into catcher #1 status for most of the summer and it ended how you might think. There’s not much bat here, but the Pirates have been carrying the corpse of Henry Davis‘ bat, so why not make him a platoon partner that can hold up the defensive side of the deal. Romo has one minor league option remaining as well, so this is basically a need for need deal with the White Sox receiving the upside and the Pirates receiving the downside protection.
Milwaukee Brewers
White Sox send: Kyle Lodise ss; Alex Weingartner twp; Blake Larson lhp
White Sox receive: Trevor Megill rhp
Rationale: A White Sox playoff run where they could trust basically 1.5 high leverage arms changes the way one thinks about a bullpen. Megill is in his final arbitration year and will turn 33 next month so this is exactly the kinda trade the Brewers make all the time. You watched the World Series, their bullpen is deep af. They cash in chips like this all the time. And when they do, they usually make good on them. It inherently makes me mad that they would probably get more out of these kids than the White Sox probably would. Clearly Megill allows the White Sox a lot of optionality with both usage and roles for Grant Taylor and Hagen Smith. Getz wanted a closer last year, Seranthony Dominguez didn’t work out, here’s another approach.
The White Sox trade three newbies if you will. Larson was drafted in 2024, but he’s only thrown 4 2/3 professional innings to this point. Weingartner has only received his signing bonus and has yet to actually play any professional ball. Lodise is the outlier, playing 139 games at high A and been totally decent, hitting 24 HR, stealing 49 bases and scoring 104 runs. He was also an accomplished college player so the rubber really meets the road next year when he hits AAA. Someday the White Sox will be stacked enough to make re-stocking style trades like this, but let’s just try and get back to the playoffs first.
About The Author
chorizy
Section 108 Row 13, Bassist for Barren Plains, Acclaimed drunkard