How Do the White Sox Handle the Dylan Cease Situation?

A trade revolving around the 2022 Cy Young runner-up makes a lot of sense for a White Sox team in serious need of retooling.

CHICAGO, IL - SEPTEMBER 20: Dylan Cease #84 of the Chicago White Sox pitches in the first inning against the Cleveland Guardians at Guaranteed Rate Field on September 20, 2022 in Chicago, Illinois. (Photo by Jamie Sabau/Getty Images)

The Chicago White Sox enter the offseason with the mission of establishing a new culture inside the organization with a new front office at the helm. I detailed the entire roster and everything that needs to happen this winter in the White Sox offseason outlook, but one key decision deserves more direct attention.

The team is in need of serious retooling as the organization points focus toward 2025 and beyond, and the question remains whether or not they will trade any of their stars. The roster has minimal pieces with value at the moment, but two key players remain who could be on the move if the right deal materializes this winter.

It feels as though a Luis Robert Jr. trade is unlikely to occur, with him having four years of team control and Chicago needing some form of stability to build around. There is still a possibility that a team blows the White Sox away with a package that sways them to move their star center fielder, but a trade revolving around the 2022 Cy Young runner-up makes a lot more sense.

Dylan Cease entered 2023 as the clear ace of the staff but regressed significantly with troubling metrics, especially in the first half of the season. He finished the year with a 4.58 ERA and a 27.3% strikeout rate, after finishing the year prior with a 2.20 ERA and a strikeout rate over 30%.

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Despite his down year, there is no doubt that Cease has some of the best stuff in the game, and his FIP of 3.72 indicates that he was at least a little unlucky. He probably witnessed regression partially due to the nature of the roster around him, which was one of the worst in baseball.

The results from 2023 may not show it, but the stuff is still there, and Cease will be in high demand, given the market for pitchers in the modern era of baseball.

He is still just 27 years old with the upside to be one of the better pitchers in baseball any given year. With two years of team control left, the White Sox face an incredibly precarious situation when it comes to their ace.

Cease’s name was the biggest, aside from Shohei Ohtani, floated at the 2023 trade deadline, and he’ll be up there once again this winter.

Under no circumstance will the White Sox sell low on Cease based on 2023 performance. While they may not receive what they could have after 2022, they will expect a huge package of talent in return for his services. With the current status of pitching around the league, plenty of teams would love an arm with elite stuff and a track record of durability over the past few years.

Realistically, Cease’s trade value is probably that of a mid-to-low-threes ERA pitcher – in essence, somewhere between his 2022 and ’23 seasons. While the White Sox would love to keep Cease as part of their future contention core, he may be out of the door before the team is ready to seriously contend.

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Despite the White Sox not having much of any pitching depth, it’s seriously worth considering moving Cease, whether it be in the offseason or at the deadline, in order to maximize his value – he is under team control through the 2025 season. Teams looking to acquire a front-end pitcher via the trade market won’t be able to do much better than two years of Cease.

The best option for the White Sox may be to wait for the signings of the top starting pitchers on the market. Aaron Nola, Blake Snell, Yoshinobu Yamamoto, and Jordan Montgomery are all likely to receive five-year contracts (or longer) in free agency this year, but teams hoping to contend that fail to sign one of them will be heavily pursuing arms through trade. The White Sox have to be patient with the market to capitalize on their situation.

A deal for Cease would require at least two high-end prospects, and the White Sox will certainly not settle for a package lesser than the price they have established. There are not many teams that have a clear need for Cease and have a deep enough farm system to make it happen.

The prime teams with a chance to make the move appear to be the Orioles, Dodgers, Reds, and maybe a few others. The match between Chicago and Baltimore has been heavily discussed since last year and still makes the most sense of these options.

Chicago is not in a position to compete while Cease is still under contract, and an extension with their ace feels improbable with the current status of the team – even more so considering his agent is Scott Boras. If a team is going to match the asking price, the White Sox have to consider striking while the iron is hot, given the two years remaining before Cease becomes a free agent.

Waiting until the trade deadline in hopes that Cease will rebuild his value with a big first half would be a valid choice, but he would have to increase his value enough to compensate for the shorter timeframe in which he would be under contract with his new team. If Cease performs similarly or only slightly better than he did in 2023, the White Sox would likely receive less in a deal.

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There are plenty of issues to solve for the White Sox, but the best way for the team to stockpile additional talent is through a Cease deal. This may be one of the final offseason decisions made by the organization, given the nature of free agency, but it could be the most pivotal one made this winter.