The Five Best Dylan Cease Mock Trades for the Chicago White Sox

It’s no secret that the market for reliable starting pitching is hotter than ever right now. With top free agent arms Yoshinobu Yamamoto and Blake Snell still on the market, it’s safe to say that nearly every team that hopes to contend is still looking to add pitching.

With a clear retool on the way, the White Sox find themsleves in prime position to take advantage of the market and cash in their top trade asset in Dylan Cease.

The starting pitchers to sign this offseason have all gotten more value than most expected them to this winter. With veteran arms that project as back of the rotation pitchers at this state of their career signing deals in the $11 to $14 million range, Cease is becoming an even more attractive option.

Cease is coming off a disapointing 2023 season, but he flashed ace-upside in 2022 and his advanced numbers show a guy due for some positive regression next season. Projected $8.3 million in arbitration by Spotrac next season, Cease is more affordable and a much higher upside arm than many that have been signed this winter. Additionally, he comes with a second year of control.

The complication in regards to prospect return to where a potential trade becomes trickier in comparison to free agents, but soon enough a team will become desperate enough to part with assets. Once some of the top free agents are signed, teams left without a major addition to their rotation are likely to shift focus to Cease, especially with Tyler Glasnow now off the market since he was moved to the Dodgers.

One team has been the obvious logical choice for Cease since his name entered the trade market at the deadline and many others have began to seem more realistic with time. While the Dodgers are going to load up in any way they can, I don’t see them adding another arm they will have to then extend like they did with Glasnow. In reality, it wouldn’t suprise me if the Dodgers made it happen with their perenially loaded system, but I’m not including them here for now.

These five teams fit the bill as teams with a clear need for a starting pitcher with upside and the assets that could entice the White Sox to finally make the move. These potential trade packages could all be adjusted with different prospects, but represent where I see the value ending up on a Cease deal.

Trade One: Baltimore Orioles

The team that just about everyone has mentioned here still feels like the best fit. The Orioles have the consensus top farm system in baseball with loads of position player depth at essentially every level of their farm right now. However, they have a clear lack of pitching depth and a need for another rotation anchor alongside 2023 breakout Kyle Bradish and young star Grayson Rodriguez.

This truly just feels like the perfect match, but Baltimore has continued to be hesistant to move any of their top young prospects. That can’t continue to be the case and they’re going to have to part with some assets one way or another in order to add pitching without having to spend a ton in free agency which they never tend to do.

The Orioles have ample league-ready position players particulary at positons which Chicago needs to address this winter. The White Sox do not currently have a clear starter in either right field or at second base heading into 2024. Furthermore, while Paul DeJong was signed to be a stopgap at shortstop while Colson Montgomery grows, it wouldn’t hurt for the Sox to add a player who could play there at times as well.

Baltimore is not going to move top prospect Jackson Holliday in any deal and Samuel Basallo feels borderline untouchable given his offense upside and age.

I don’t believe that Coby Mayo (Just Baseball’s 12th-ranked prospect in baseball) is going to be an option either but would be an optimal target if he were to be available. The highest upside hitter left for the White Sox to target happens to be someone that would slide immidiately into a starting role in right field for Chicago.

That would be former top pick and our 31st-ranked prospect Heston Kjerstad. After a brief taste of the MLB level in 2023, Kjerstad is ready to be a full-time player at the level but the Orioles have Cedric Mullins, Anthony Santander, Austin Hays, and other young players set to lead the outfield as well.

Kjerstad could get enough at-bats by backing up both corner outfielder spots and playing some first base or designated hitter, but could also be used the headliner in a deal for Cease. He’s coming off a season in which he dominated Double-A with a 160 wRC+ before reaching Triple-A and eventually the big leagues. While his numbers regressed in Triple-A, his power upside and strikeout rate only around 20% inspires confidence in his development.

Fellow outfield prospect Colton Cowser (JB #36 prospect) could fit into this spot too, but his defense and contact skills make him more of an ideal rotational player in Baltimore and less interesting to a White Sox team in search of offensive upside in right field.

Either of those two could fit as a key piece, but Kjerstad makes a little more sense for the White Sox even though he may be valued a little higher by Baltimore right now.

The outfield is strong, but the Orioles infield is the deepest of any in baseball right now with reigning Rookie of the Year Gunnar Henderson and top prospect in baseball Jackson Holliday headlining the core.

The Orioles have a handful of middle infielders that simply cannot all receive playing time and none of them may even have time in the near future. The three main pieces that I see in this category are Jordan Westburg, Joey Ortiz, and Connor Norby.

Westburg showed some promise with the Orioles in the second half of the season after dominating Triple-A while playing second, shortstop, and third in Baltimore. He flashed above-average defense all over the infield and would easily start for the White Sox at second base.

Ortiz (JB #43 prospect) didn’t have a real shot to contribute with Baltimore as he only appeared in 15 games, but the 25-year-old is an exceptional fielder with premium contact skills and the ability to provide more offensively. He batted .321 in Triple-A last season and continued to maintain a low strikeout rate.

Norby (JB #76 prospect) has raw power but is less proven than either of the other two infield headliner options. With a simple swing and upside that could grow, Norby is still a rather interesting option.

The White Sox would love to find an immidiate option for two of their biggest holes via this trade and the Orioles may be the only team that could truly make that happen. However, the White Sox would love to add at least one pitcher in a Cease deal as they’ll losing their best arm.

While they don’t have a higher-end pitching prospect, Cade Povich or Chayce McDermott could fit well as a third piece in this deal.

Given the status of their system, the Orioles could part will three strong assets and still have one of the best farm systems in the league. These two teams feel the perfect trade partners and it will just come down to whether or not the Orioles meet the asking price.

Proposed Deal: Heston Kjerstad, Joey Ortiz, Cade Povich, and Justin Armbruster

Trade Two: Cincinnati Reds

The two leaders of the pack in this race for Cease are young teams in need of rotation help in order to take the next step forward. The Reds are a step behind the Orioles right now but seem like they could be the more aggressive of the two this winter based on what we’ve seen from them so far.

They made a splash offensively by adding Jeimer Candelario to their very talented infield. They also added some pitching depth via Nick Martinez and Emilio Pagan. With some holes already filled and an offense with almost too many options similar to the Orioles, the Reds only clear need right now is more rotation help.

The young pitchers in Cincy are expected to take another step with health hopefully on their side, but they definitely could use an innings eater with upside to make a huge difference. That’s exactly what Cease brings to the table with two years of team control and at least 32 games started in the past three seasons.

As mentioned prior, the White Sox have certain positions they will be looking to acquire, but they ultimately will look to get as much value as they can out of Cease. With a goal for Chicago to restock talent in order to start competing in 2025 and beyond, the Reds could present a package of assets that could beat any other team aside from Baltimore.

The Reds do not have the league-ready offensive pieces Chicago may seek, but they could change the overall talent pool within the White Sox system.

A package from Cincinnati would start with one of their pitching prospects as the White Sox would want a top arm given that they wouldn’t get a star position player in the deal. Rhett Lowder or Chase Petty would be the options that make the most sense with Connor Phillips also being a potential candidate for this deal.

Lowder was a first round pick this past summer but is expected to rise through the ranks quite swiftly given his experience at the highest levels of college ball. Petty has dealt with injury issues and has not thrown many innings, but has the stuff of an ace with probably the most upside of any pitcher in the Reds’ system. Meanwhile, Phillips has a lethal fastball and breaking ball combination and made his debut in 2023, but still struggles a lot with his command.

The Reds have a variety of exciting infield pieces with a Major League roster already filled with young stars who were top prospects before the 2023 season.

Edwin Arroyo (JB #98 prosopect) is an elite middle infielder defensively and continued to make strides at the plate with an aggresive approach but strong bat-to-ball skills. The Reds also have two mashers at the lower levels in Cam Collier and Sal Stewart who are nowhere league-ready but have tons of upside to dream on. Stewart walked more than he struck out in 2023 and has flashed serious pop, while Collier was a first round pick and is extremely projectable at just 19 years old.

The Reds system has many other young infielder options such as Carlos Jorge, Sammy Stafura, and Ricardo Cabrera as well as some interesting potential outfielder flyers like Rece Hinds and Blake Dunn, who the White Sox would have interest in as a third or fourth piece.

With a well-rounded group of assets and the offensive depth already at the MLB level, the Reds could part with one top arm and a few hitters in order to add a trustworthy rotation option alongside the young group of Hunter Greene, Nick Lodolo, Graham Ashcraft, and Andrew Abbott.

Proposed Trade: Chase Petty, Edwin Arroyo, Sal Stewart, and Blake Dunn

Trade Three: Atlanta Braves

Imagine entering a series and having to face Max Fried, Spencer Strider, and then Dylan Cease. There is a world where the Braves make this happen as they’re not expected to be a big player in free agency this year but are looking to add pitching to a team that is already set up well.

The problem for Atlanta is a farm system that lacks any high-end position player talent right now. The White Sox are in need of both facets, which makes it feel like a deal would need to involve at least one asset who could be part of their lineup soon.

With that said, the Braves could put together a rather exciting group of upside arms. Given a lack of positron players, the deal would almost certainly have to start with either AJ Smith-Shawver or Hustron Waldrep.

Smith-Shawver (JB #45 prospect) made his debut with the Braves in 2023 at just 20 years old after being pushed through the system incredibly quickly. He made just five starts between High-A and Double-A to start the season, allowing no runs in 21 innings pitched between the two levels.

The Braves turned to him midseason with a depleted rotation causing issues for them and he appeared in four games in June. He spent most of the second half in Triple-A but made two more spot starts with Atlanta.

Drafted this summer, Waldrep comes with some reliever risk given his relliance on a splitter but he looked excellent in his first professional stint. He made starts at all four levels of the minor leagues as he threw his last game of the year in Triple-A. In eight starts across the four levels, Waldrep pitched to a 1.53 ERA with 41 strikeouts in 29.1 innings thrown.

Beyond those two, the Braves have a plethora of young pitchers with upside that could intrugue the White Sox. This group is headlined by recent high school draft picks Owen Murphy and JR Ritchie in addition to 23-year-old Spencer Schwellenbach, who was excellent in his first season after undergoing Tommy John Surgery after being drafted.

The Braves have minimal options to offer on the other side of the ball, but former top prospect Vaughn Grissom could be a worthy reclaimation project for Chicago.

This trade would only be possible if the White Sox were okay prioritzing pitchers and looking elsewhere for right field help and other offensive prospects. It remains to be seen whether or not they would do that, but they could get multiple arms with a chance to be rotation pieces for the long-term future.

Proposed Trade: AJ Smith-Shawver, Spencer Schwellenbach, Vaughn Grissom, and Diego Benitez

Trade Four: San Diego Padres

The team with the most complicted agenda this offseason slots into the fourth spot here as an under-the-radar option that I’ve began to consider more closely lately. We already established the needs of the White Sox, so let’s look at how they match up with the San Diego farm.

Similarly to the Braves package, an upside arm would be the headliner of a deal with the Padres. Catcher Ethan Salas and shortstop Jackson Merrill are untouchable in almost any deal which makes the clear top two trade options left-hander Robby Snelling and right-hander Dylan Lesko.

Snelling (JB #32 prospect) was the breakout prospect of the year for the Padres as he moved through three levels of the minor leagues and dominated every step of the way. He was Just Baseball’s Minor League Pitcher of the Year, pitching to a 1.82 ERA acorss over 100 innings pitched as he finished the year in Double-A.

With an above-average fastball and breaking ball combo and strong command, Snelling could be a Major League option soon despite being just 20 years old.

Lesko (JB #69 prospect) could have been a top pick in the draft but ended up going 15th overall out of high school in 2022 after undergoing Tommy John Surgery. Lesko will need to ramp up his innings, but flashed his top-end fastball and changeup with 52 strikeouts in his 33 innings back on the mound this summer.

One of those two would be a great get for the White Sox. The Padres also have two additional arms that would be worth looking at as secondary pieces. Jairo Iriarte (JB #87 prospect) is a true power arm and he took a huge step forward this past season and Adam Mazur was excellent in his first professional season with a deep arsenal and strong command.

Chicago would want to take advantage of the outfield depth in San Diego’s system. Dillon Head was linked to the White Sox before being drafted and could be a quick riser with top notch speed and an improving hit tool at the plate. Jakob Marsee took a step forward this seaosn and could rise quickly at 22 years old.

The Padres don’t have the strongest system but could entice the White Sox with a package centered around one of their two elite arms with some additional assets. San Diego was forced to shed salary this winter and their best option to add a starter they seriously need could be via trade.

Proposed Deal: Robby Snelling, Jairo Iriarte, and Jakob Marsee

Trade Five: Texas Rangers

This is the longshot of the group as this would be rather unlikely but almost could work. The Rangers just won the World Series and they look ready to defend their title next season. However, they have serious injuries that could cause them to approach the pitching market.

With Jacob deGrom, Max Scherzer, and the recently signed Tyler Mahle all expected to be out until at least the All-Star break, Texas needs to fill out their rotation for the first half of the season. While it likely means they’ll add some veteran pitching at a lower cost to keep them going until their stars return, they could just decide to add another star.

The Rangers could afford Cease at least over the next two years before he hits free agency and he would take their rotation to the whole next level. Texas has the deepest offense in the American League with more talent waiting in the wings. They have the ability to swing a deal for another star like Cease.

Postseason star Evan Carter and top prospect Wyatt Langford are going nowhere and will both be major pieces of the MLB roster next season at just 21 and 22 years old respectively. They are certainly both untouchable in a trade, but the Rangers have a variety of hitters and pitchers that could appeal to the White Sox.

Right-handers Brock Porter and Jack Leiter have plenty of upside on the mound but each come with their own risks. Porter’s innings were limited in his first professional season but he features an elite fastball and changeup with a developing slider. Leiter was a top pick but has struggled thus far in his career. He still possesses immense upside though given his track record. One of these two may not be quite good enough in comparison to other possible headliners.

Justin Foscue and Dustin Harris feel like obvious fits in this deal as they’re both just about league-ready and play positions of need in Chicago. Foscue is blocked by the loaded infield in Texas, but has an excellent approach and plus power for a second baseman. Harris is already 24 years old and has no room for playing time in the outfield. He’s a well-rouded corner outfielder who can chase too often but draws walks and has maintained an OPS over .800 in every minor league season.

The Rangers have a variety of other mid-level pieces such as Owen White, Aaron Zavala, and Anthony Gutierrez that could be of interest in a deal too.

This trade possibility is still less than likely, but the more time I spend considering it, the more I like it. The Rangers may not need to make a move of this scale, but they could and it would be awesome to watch.

Proposed Trade: Brock Porter, Justin Foscue, Dustin Harris, and Anthony Gutierrez