White Sox “Trades” with EVERY TEAM | AL East Edition | 2026

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: Edgar Quero C
White Sox receive: Tre Morgan 1b, Joe Rock LHP
Rationale: The White Sox catching duo of Edgar Quero and Kyle Teel were the belle of the ball in 2025, with both players showing much of the prospect shine promised by White Sox brass and Prospect Hounds alike. Now with clear eyed vision heading into 2026 and with this sort of excess value if you will, you must at least give some attention to the potential to re-position yourself. The Rays are dying on the vine for catching talent, even trading with the White Sox during the 2025 season for Matt Thaiss (which didn’t go well for them). Anywho, Quero is a perfect fit on this roster.

In return, the White Sox get 1b Tre Morgan who is a consensus top 100 prospect, although a very odd profile for a 1b. This is an extreme glove 1st player, possibly an 80 at the cold corner. Think Keith Hernandez light. It’s not the most modern profile but it certainly has value on a roster and in an organization that really needs to improve it’s defense.

As a topper, the White Sox also acquire Joe Rock. That’s just a great name. That guy could be fronting your local hair metal cover band. That guy could be the guy manning the jackhammer on the construction site. He could be both!! In this reality he’s a crafty lefty that profiles as a back end guy, sound familiar? Banny loves these guys. You love these guys!! #ChicagoTough!

New York Yankees

White Sox send: Luis Robert Jr. CF
White Sox receive: Bryce Cunningham RHP, T.J. Rumfield 1B
Rationale: Last year, I traded Luis to the Yankees for a binder full of prospects and it fell flat with all of yous.

White Sox “Trades” with EVERY TEAM – AL East Edition – 2025

Now, here we are a year later and the Yankees are in a lesser position of need as Spencer Jones nears the majors and the price on Luis has dropped.

The return for Luis now is two prospects that while not highly touted, seem like very good projects for Brian Bannister and Ryan Fuller.

In Cunningham, you have a potential middle of the rotation guy with a great change up who needs more movement on his fastball and improvement on his third pitch.

In Rumfield, other than T.J. Rumfield being a great baseball name, you have a first basemen with a consistent bat, but not quite enough power. Developing even just a little more power could easily push him onto the White Sox starting 9.

Baltimore Orioles

White Sox send: Tanner McDougal RHP, Jairo Iriarte RHP
White Sox receive: Enrique Bradfield Jr. OF
Rationale: We have gone in great detail to point out how the White Sox starting rotation is far from set. Let’s also not neglect that centerfield is going to be vacated as soon as the team decides paying $20 million a year to Luis Robert Jr. is no longer fiscally responsible. I also like to think that when you start turning 5th round picks into 45 FV players, it’s okay to flip them out and take your profit no matter the newly found upside you have created.

In Bradfield, the White Sox would have their centerfielder of the future, albeit in a retro style player. Think Lance Johnson. Elite speed and range in centerfield, strong bat to ball skills and overall plate discipline, bunting as a weapon, NO POWER! That’s what you get with Bradfield who received a promotion to AAA down the stretch last year and is minutes from being able to take over the reigns in center even if his promotion would be more urgent in 1986, than 2026.

The aforementioned McDougal was shot out of a cannon this year, with a 28% K-Rate across A+ and AA and a 3.15 FIP over 113 1/3 Innings Pitched. He’s a rising star in White Sox system that can hit upper 90’s. Still, he hasn’t escaped the embryodic phase that still contains significant reliever risk, but the upside is definitely there and for an O’s org drowning because they can’t build out a rotation, a worthwhile gamble. But best of all, it’ll remove KFidds high school baseball over-analysis from our beloved White Sox Twitter.

Jairo Iriarte is just here because all that promise and extension still exist and the White Sox can’t figure him out. As Chorizy has noted on the 108 podcast, this is the “save face” portion of his tenure with the White Sox, where Chris Getz attaches him as a tail to a trade he wouldn’t have been involved in just to proport there is some liquidation value.

Boston Red Sox

White Sox send: Hagen Smith LHP
White Sox receive: Jhostynxon Garcia OF
Rationale: Let’s consider this a litmus test for where you are personally at with Hagen Smith. Some of yous reading this would snap call an offer like this to get out from under the #5 overall pick in the 2024 Draft. Others will absolutely turn up their nose at trading a pitcher with Smith’s pedigree for a tweener outfielder with all fields power. I look forward to the discussion.

Hagen Smith’s prospect value has tumbled steadily since the moment he showed up brandishing a mustache that Chorizy DID NOT approve of. Brian Bannister’s main function, other than running the entire pitching apparatus, seems to be voicing the opinion that Smith is fine and “working on things”. It’s been poor command and control. It’s been a loss of velocity. It’s been underwhelming in game performances. Now mind you, he started straight into AA after his killer junior year of college and nobody really squares him up. So the future ace still seems to be in there somewhere, but shows up less than Michael Myers on Halloween.

The Password aka Jhostynxon Garcia has seen a steady rise of his prospect status finally landing right around where Smith is in the MLB Pipeline top 100. He’s listed at 6’0″ 163lbs on the team site, but even a moderate amount of digging will lead you to find out that he’s between 50 and 70 lbs heavier than that. It’s all fields power, big bat speed and high exit velos! He can play centerfield (for now, we mentioned his thiccness) and has an arm that is passable in right field. There is still a ton of chase here that could either eat the profile with strikeouts (was still a 29% K-Rate in AAA in 2025) or limit the all fields power. Still fun to dream though and he’s basically ready to be in the majors now. The only problemo is the BoSox are absolutely stacked in young position players in the majors, so they do need to move at least one of the chess pieces. Hmmmm….

Toronto Blue Jays

White Sox send: Shane Smith RHP
White Sox receive: Arjun Nimmala SS
Rationale: As I’m writing this, the Blue Jays are heading into Game 7 of the World Series against the Dodgers. It’s hard to imagine the White Sox offering them something of value, BUT we have to look at 2026. With Max Scherzer leaving and Shane Bieber likely leaving (he has a $16M player option, but can opt out and get $4M + whatever he gets on the open market), the Blue Jays get thin at pitcher real quick. Kevin Gausman will remain at the top of the rotation, Jose Berrios will be back, and Trey Yesavage has left such an impression that I didn’t even need to check the spelling on that. But then it gets thin. Yariel Rodriguez factors in, but the highly touted prospects in the minors are dealing with elbow injuries. They can surely go to free agency as well. But they can also trade for a starter.

Not that the White Sox have a wealth of pitching, but Shane Smith shot out of a cannon this year and made the All Star Team. He was about the best result you could get out of a Rule 5 pick and will likely over inflate the confidence of White Sox fans in Rule 5 picks for the next decade. That said, he is a valuable asset for the White Sox if they were willing to trade him.

On the flipside, Arjun Nimmala is one of the top prospects in the Jays system and he has real power at shortstop. The tools are seemingly there and he projects well, but there are still questions. And then there is a big hovering question, what happens with Bo Bichette? If Bichette remains a Jay for an extended period of time with Andres Gimenez also signed through 2029, the fight between Nimmala and JoJo Parker for a roster spot becomes increasingly difficult.

In general, it’s difficult for me to see a trade like this come to fruition, but it would show some tremendous huevos on both GMs to do it.