White Sox “Trades” with EVERY TEAM | AL East 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 AL East Edition.
The Au Jus
Tampa Rays
White Sox send: Billy Carlson SS, Tanner McDougal RHP
White Sox receive: Shane McClanahan LHP
Rationale: This is not your normal Rays trading a guy who’s getting too expensive. This is them trading a guy they can’t trust to stay healthy. When McClanahan is healthy, he’s a really good pitcher. Unfortunately, his recent vintage has not been very healthy. That said, I think the Sox can handle this type of risk. With a handful of SPs with options including Noah Schultz, David Sandlin, Drew Thorpe; you can take this type of risk.
Now, the Rays aren’t just gonna give him away. It’ll cost ya a premium prospect, but it should be realistic as to what you’d send for a pitcher that didn’t finish out the year. Billy Carlson is part of a an infield logjam, but he’s still a top guy in the prospect rankings for the White Sox. The upside of his glove alone should intrigue the Rays.
Tanner McDougal is a guy that I really don’t wanna give up, but he very much feels like a guy the Rays would want.
This quickly becomes a high risk, high reward trade. Ride the Snake!
New York Yankees
White Sox send: Grant Taylor rhp
White Sox receive: Elmer Rodriguez rhp; Yostin Pena of; Jasson Dominguez of
Rationale: I love Grant Taylor! I know yous won’t believe me because I have suggested that he was a great trade piece. I still believe that. He’s a great real life pitcher as well. I’m not one of these people, but there are many White Sox fans that have been pondering, “What if we made Grant Taylor a Starting Pitcher?”. Well, here you go!!
Elmer Rodriguez is a highly touted, highly ranked starting pitching prospect in the Yankees system. He’s probably not the same type of starting pitcher that Grant Taylor would be, but an effective profile nonetheless. Rodriguez’ upper minors profile denotes him throwing mid 50’s percent ground balls, which is totally nuts and exceptionally playable in Sox Park. He had a brief cup of coffee with the big league club in 2026 and it didn’t go great, but he safely slides into your rotation in 2027. As long as he maintains strong command, you can sit back and watch the groundballs roll in.
As good of a prospect and future as Rodriguez is likely to have, he’s not quite enough to get Taylor. Enter Yostin Pena. He’s 19, he’s 6’4″, he’s a centerfielder currently with a ton of speed and a ton of fricking power. He’s still in A ball. He doesn’t require Rule 5 protection until 2030…lol. There’s still a lot of chase here and he might fill out more, so maybe it’s right field instead of center field, but even with that it’s huge power and a top outfield throwing arm in the minors. His age fits nicely with Chris Getz‘ next group of prospects that will be coming through as I discussed with Ian Eskridge on a recent episode of the Au Jus.
Dominguez was the belle of the ball just a few years ago, but underwhelming performance and Yankees mismanagement at the big league level leave him down to his final minor league option and nowhere to play in the Bronx. Chris Getz has mentioned wanting to prioritize adding in the outfield. Dominguez has a speed and power profile. He just hasn’t truly produced at the big league level. He’s still got tremendous bat speed, he still has tremendous foot speed. He’s a gamble as well, but the upside is still there.
Baltimore Orioles
White Sox send: Jairo Iriarte RHP, Samuel Zavala OF
White Sox receive: Christian Encarnacion-Strand 1B/3B
Rationale: When I initially looked at this team, Blaze Alexander looked like someone the White Sox would like. However, I don’t see the O’s trading him. I also looked at Tyler O’Neill, but between his recent injuries and his salary ($16.5M in 2027), I had trouble making anything work.
The Orioles do have a bit of a logjam at the corner infield position, which is not a big need for the White Sox, but I think we can make it work. With Pete Alonso at 1B, Coby Mayo, Jordan Westburg, and Christian Encarnacion-Strand will all be vying for time at 3B and DH. And you have to assume Samuel Basallo will eat up some of those DH plate appearances. This is probably the best opportunity for the O’s to improve the team, trading one of these guys. Which likely means Mayo or CES.
I think for the White Sox, this isn’t a major need, but the ability to spell Munetaka Murakami or DH him without having to move Miguel Vargas off 3rd base is a nice option. Mayo might bring to much of a prospect price tag for what the Sox are willing to give up, so let’s focus on CES. He should be the cheaper option as the Orioles did just get him for cash a few months ago. Since then, he has hit the snot outta the ball, so the price has gone up. But I don’t think it’s extremely high.
In return, the Orioles get some prospects nearing their expiration date. With Iriatrte, you could see him making a major league team and Zavala is someone people still believe in. Not a sexy package, but CES was moved for cash not very long ago.
As I look at this, my personal thought is that the O’s would be best served to take a chance on Encarnacion-Strand and see what they can get for Mayo from a team with a greater need.
Boston Red Sox
White Sox send: Shane Smith RHP, Christian Oppor LHP
White Sox receive: Jarren Duran OF
Rationale: It’s just crazy to me that we’re at the point that there is consideration of non-tendering Jarren Duran
Do the White Sox need another left handed outfielder? Why the hell not!
Are you worried about Duran yelling at the third base coach? That’s just fire and passion where I come from
Is he cooked? God, I hope not
Is he worth his projected $11M arb? Prolly not
We’re buying low here team. Jarren Duran was a 9 bWAR player in 2024 and just under 5 in 2025. It all fell apart in 2026 and that combined with some of his antics and an upcoming arb number around $11M, the idea of him being dealt before November 20th seems likely. While he’s not a great fit, this seems like an opportunity to grab an impact player for way less than you normally would.
In return, a homecoming for Shane Smith. He’s the main piece here and it’ll be up to the Red Sox to help him turn it around from his 2026. Even as a reliever, he can have an impact.
Staying with everyone involved falling apart in 2026, Christian Oppor is a lottery ticket in this one.
It seems light, but the fact that he might just be out there as a non-tender changes the price in my humble opinion.
Toronto Blue Jays
White Sox send: Sam Antonacci of / 2b
White Sox receive: Jose Soriano rhp
Rationale: The White Sox currently have two major league regular caliber second basemen. I CAN’T BELIEVE I JUST TYPED THAT AFTER WHAT THE LAST TWENTY YEARS HAS LOOKED LIKE!!!
The White Sox don’t necessarily need to trade Sam Antonacci, but having him at DH or playing a well below average LF is an inefficient use of his talents. Trading Antonacci while painful given both his production and his popularity with the fanbase is likely the best way to acquire something that the roster could really use. Ernie Clement is absolute toast. He was great in the Jays World Series run in 2025 and he was horribad in 2026. Cooked. Finished. The Jays need a guy like Sammy the Ant.
Jose Soriano is a guy the White Sox would’ve loved to get at the deadline. The Jays barreled a top 50 prospect for him as they sort of bought and sold. Soriano is a free agent after the 2028 season, so he’s controlled for two more years. This feels like one of the evenist (that’s probably not a word) trades I could make. Both teams fill a huge need on their respective rosters.
About The Author
chorizy
Section 108 Row 13, Bassist for Barren Plains, Acclaimed drunkard