White Sox “Trades” with EVERY TEAM – NL West Edition – 2025

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 West Edition.

The Au Jus

Los Angeles Dodgers

White Sox send: Colson Montgomery ss / 3b
White Sox receive: Josue De Paula of, Ben Casparius rhp
Rationale: Despite winning the World Series in 2024, the Dodgers left side of the infield was a question nearly all season. They even went as far as Mookie Betts at short for a chunk of the season to sure it up. Miguel Rojas is here, Tommy Edman who is more utility man than shortstop is also here, Alex Freeland is on the way, but the combination of shortstop being a question mark and running out a 34 year old Max Muncy at 3b, it would seem the Dodgers could use reinforcements. They’ll probably just increase Willy Adames net worth to 9 figs, but in case that plan falls through I could see them wanting to add another ss / 3b to the mix with good plate decisions and power potential. Montgomery is obviously a top prospect in baseball so you need a big prize in return.

Josue De Paula is 19, with monster upside at the plate, he takes walks, he has speed, his power is coming into his own and with a body that could fill out more and provide even more power! An electric left handed hitting outfield prospect. Ben Casparius is a reliever prospect who actually just pitched in the World Series, he served as an opener in Game 4. It’s a good slider and not much else plus, but he’s the throw in here and could allow the White Sox to leverage him as a smaller trade asset if he works coming out of the pen. The thought process in trading high end prospect for younger high end prospect is just giving the organization time to continue to accumulate talent. It’s unorthodox, but might just work.

San Diego Padres

White Sox send: Garrett Crochet lhp, Luis Robert cf
White Sox receive: Leodalis De Vries ss, Humberto Cruz rhp , Cobb Hightower ss/2b, Jhony Brito rhp
Rationale: Crochet joining Dylan Cease in the Padres rotation will definitely make some White Sox fans violently ill. And Luis Robert joining Fernando Tatis Jr.in an absolutely insane outfield won’t make those fans feel any better. While White Sox fans, including myself, value these two players very highly, there is a short sample size on Crochet and volatility in Luis’s performance including injuries. This lead me to combining them into this trade to be able to headline it with Leodalis.

This is a trade that I could see both fan bases saying “F that!” From the Padres side, this is advantageous not only from the quality of the player, but the price. Crochet is a cheap starter and Luis, if he’s going well, also a deal.

For the White Sox team, they get a lot of fresh talent (copyright MSS). None of the first 3 will be able to legally drink when they land in Chicago. First up is Leodalis who had this in his Fangraphs write up:

There are international scouting personnel whose club reports on De Vries said “everything is at least plus” and think he’s a no-doubt shortstop with a 60- or 70-grade arm and a projectable frame

That’s the exact type of prospect you want and he just turned 18. Starting to build the next wave of prospects around him is a no-brainer.

Humberto Cruz is a pitcher who Fangraphs had as the #15 prospect in the Pads system in July. MLB currently lists him at #5. So there are varying views on the about to turn 18 year old pitcher from Monterrey. He doesn’t throw very hard, high 80s, low 90s. But he features a sinker, which plays well in Chicago.

Cobb Hightower is a new addition to the Padres system as he was drafted just a few months ago in the 3rd round. While he’s listed as a shortstop, he’s projected to be a bat-first 2b. I have no problem loading up on those with how difficult it has been to fill that role.

Jhony Brito is a throw in as he may be a 40 man casualty at some point. The Yankees liked him, the Padres liked him, but poor performance and injuries have derailed his career so far. But he’s only gonna be 27 this season, so he’s a nice flyer to get on the back end of this deal.

San Francisco Giants

White Sox send: Justin Anderson rhp, Brooks Baldwin ss/2b
White Sox receive: Kai-Wei Teng rhp, Carson Seymour rhp
Rationale: The Giants roster failed them at two key spots last year, the back of the bullpen and 2b. They leaned on their bullpen for 655 innings which only produced 2.8 fWAR. For comparison, the Marlins (7.0 fWAR) and Brewers (5.9 fWAR) used their bullpens similarly with much better effect. On the second base side, Thairo Estrada was supposed to be the guy, but they ended up putting him on waivers. Casey Schmitt filled in admirably and the bat was good vs lefties, but vs righties, not so much. So Justin Anderson and Brooks Baldwin can make sense for this roster as cheap players that can fit right in for their needs.

In return, the White Sox get Kai-Wei Teng, who the Giants have seemingly given up on as a starter. His mid-80s slider is very effective, so it would be interesting to see how Brian Bannister would use it. Carson Seymour is a 6’6″ 260lb pitcher with a slider that the metrics love, but hasn’t performed. He’s rule 5 eligible and about to be 26, so the Giants may be ready to move on. For those keeping track, yes, this is 500lb of pitcher coming to the Sox in this trade.

Colorado Rockies

White Sox send: Oscar Colas of
White Sox receive: Evan Justice lhp
Rationale: Both of these teams don’t really know what to do with these guys so let’s flip them. Evan Justice is a lefty reliever with a 95 MPH heater, a decent slider and not a single solitary clue of the strike zone. He’s down to a single minor league option, so something needs to be achieved and it seems like something the White Sox can take on. Conversely, Oscar Colas has some power, some speed and not a single solitary clue of the strike zone. He’s down to a single minor league option, so something needs to be achieved and it seems like something someone other than the White Sox can take on. Easy game.

Arizona Diamondbacks

White Sox send: Sammy Peralta lhp, Jared Schuster lhp
White Sox receive: Jordan Montgomery lhp, Caleb Roberts c, $10M
Rationale: Over the course of my career, I’ve had a few underwhelming reviews from employers, but none like the one Jordan Montgomery got immediately after the season from owner Ken Kendrick:

“If anyone wants to blame anyone for Jordan Montgomery being a Diamondback, you’re talking to the guy that should be blamed, because I brought it to (the front office’s) attention. I pushed for it. They agreed to it. It wasn’t in our game plan. … And looking back, in hindsight, a horrible decision to have invested that money in a guy that performed as poorly as he did. It’s our biggest mistake this season from a talent standpoint. And I’m the perpetrator of that.”

So to think they might be willing to send him with some money and a prospect that they’re not sure what to do with, is no stretch at all.

The Sox would give up 2 lefty relief pitchers that I don’t think they’re incredibly high on and that are running out of minor league options. AZ can plug them into their pen, send em to the minors, or just cut em. It’s really about shedding Montgomery from the 40 and getting rid of $12.5M in payroll.

The Sox, in return for paying that $12.5M, get Montgomery who could bounce back. If he does, the Sox can deal him at the deadline. If he doesn’t, they can cut him. But assuming Crochet is traded this off-season, there should be innings. In Caleb Roberts you get a solid hitter, guy had 20 HR in AA last year. There are some holes in his offensive profile, but it’s overall very nice. His defense as a catcher, however, is not so good. Hoping he can get good enough behind the plate to be David Fry tells you all you need to know. That said, the Sox seem to be able to develop this skill and it’s definitely worth trying for the bat.