The story of the offseason in Chicago continues to be centered around starting pitcher and 2022 AL Cy Young runner-up Dylan Cease. The White Sox, despite the feeling among many fans, are in a powerful position given the landscape of the pitching market across Major League Baseball.
Pitchers such as former White Sox player Lance Lynn, Kyle Gibson, Luis Severino, and others have received short-term deals this winter worth double what Dylan Cease is going to be paid in 2024. It’s safe to say that the market has led to some drastic overpays, which only benefits the White Sox in their attempt to squeeze every bit of value out of their ace.
Chris Getz has made it clear that Cease will only be moved if it benefits the long-term success of the team, and that’s exactly how this situation should be handled. With star pitchers such as Blake Snell and Jordan Montgomery still available via free agency, there is no reason to rush a Cease trade, as teams will only continue to get more desperate for pitching as the other top names available sign.
It has always felt like the Baltimore Orioles were the best fit for Cease and they still are given their prospect capital and hesitancy to spend any substantive money.
Other teams have emerged recently as potential options for Dylan Cease
The Dodgers and the Reds were two options that I initially saw being logical. However, the Dodgers traded for Tyler Glasnow and signed Japanese star Yoshinobu Yamamoto, while the Reds signed Nick Martinez and Frankie Montas to supplement their young pitching core. Given their absurd spending this winter, the Dodgers still can’t be counted out just yet, but these two teams seem much less likely now.
As we scan the rest of the league for potential trade partners, the division in which the Orioles reside could present a few other prime options for Cease. After trading multiple pitchers expected to contribute at the MLB level in order to acquire Juan Soto, the Yankees are actively searching for another starting pitcher. Meanwhile, the Boston Red Sox signed one former White Sox player in Lucas Giolito, but traded another in Chris Sale, last week. That likely means that Boston is still looking to add at least one pitcher, and they’ve been linked to free agents Blake Snell and Shota Imanaga this winter.
These two historical franchises are intending to compete, and the Orioles are currently the cream of the crop in their respective division. If the Yankees or Red Sox want to catch up with Baltimore, their best route may be by taking away a prime option from them. The slightly frustrating part about examining these options is that none of these teams can even get close to the Orioles in terms of prospect return if everyone laid their chips on the table.
The issue is that Baltimore continues to resist trading from the league-best farm system as they perennially operate like one of the smallest market teams in baseball. It’s hard to fully understand why, as the Orioles could move three of their top 10 prospects in order to acquire a star like Cease, and they would still maintain a stronger farm system than these powerful division rivals.
If the Orioles do continue to hold off in hopes of getting more affordable pitching that doesn’t cost them any top pieces, the Yankees or Red Sox could swoop in and make a run at Cease in order to position themselves to push for the division. They don’t have as many top-end prospects to offer as the Orioles, but they have pieces that fit the needs of the White Sox and could make a more aggressive push to their counterpart.
The Yankees have a fascinating mixture of league-ready players at positions of need and some young projects who would inject upside into the farm system. Jasson Dominguez would be the dream trade candidate after he flashes immense upside in his first big league stint in 2023. Still, it appears that the Yankees are unlikely to move him regardless of the talented player they’d be acquiring in a deal. If he is off the table, the attention will shift to a variety of position players and pitchers within the organization.
Spencer Jones is a consensus Top 100 prospect in baseball who was drafted in the first round of the 2022 MLB Draft and profiles as a serious left-handed power hitter. He would be an excellent get for the White Sox, given his upside and the fact that he already reached Double-A in his first full professional season last year. In terms of players who would make an impact immediately, Oswald Peraza stands out as someone who could instantly start in the middle infield this season. He struggled mightily in 52 games with the Yankees last year after an impressive brief debut in 2022, but he continued to produce in Triple-A and has solid tools across the board.
The White Sox are hoping to acquire both positional pieces that can help soon and pitchers who could factor into the future rotation through a deal involving Cease. The Yankees do have both, as the aforementioned hitters would be targeted, as well as top pitching prospects Chase Hampton and Will Warren. Hampton finished his first full season in Double-A and would need another year in the minors likely while Warren finished the year with 21 appearances in Triple-A and could join the 2024 rotation.
International signings Roderick Arias and Brando Mayea would be intriguing additional pieces, too, with league-ready outfielder Everson Pereira also being an option if Jones is not attainable.
The Red Sox, on the other hand, don’t have as many optimal targets as the Yankees but have a few key pieces that they could utilize to put together a viable package. Outfielder Roman Anthony would be the clear top target despite being just 19 years old. Drafted in 2022, Anthony has risen quickly in prospect rankings with tons of power in the tank and a strong ability at a young age to draw walks. He reached Double-A last season at an incredibly young age and is very protectable.
Ceddanne Rafaela debuted last season, and his versatility and speed would be a welcomed addition to the White Sox current roster. Miguel Bleis is another very young prospect at just 19 years old, but he was one of the most trendy prospects around the league before missing most of 2023 after undergoing surgery. The White Sox would be buying low on him, but his upside is up there with any prospect in the Boston system.
It seems like New York has a little more to offer in terms of what the White Sox organization is targeting right now, but both of these teams appear to be at the least considering a Cease deal. As mentioned before though, this may not even matter if the Orioles decide to pony up eventually.
Baltimore would never trade top prospect Jackson Holliday, but they could put together a package with a pair of their top 100 prospects in addition to another player or two. Heston Kjerstad is exactly what the White Sox could use as someone who would start in right field and has ample power from the left side of the plate. Any of Joey Ortiz, Jordan Westburg, or Connor Norby could be the primary second baseman in Chicago in 2024. While they are not surefire starting pitchers, Cade Povich or Chayce McDermott would be a nice addition to a deal as pitchers with experience in the upper minors.
The Yankees feel like the one team that could get risky and make an offer that the White Sox would take instead of holding out for a Baltimore deal, but I can’t see it happening without Spencer Jones being involved, and the Yankees are reportedly hesitant to move him. This still feels like the Orioles race to lose but this situation feels like it’s going to drag on for a while still with so many free agents yet to sign.
Cease is still highly likely to be moved, according to most reports, but Getz has made it rather clear that he is not going to settle on a deal purely for the sake of getting it done. I expect at least Blake Snell and Jordan Montgomery to sign prior to a Cease deal happening, and there are still other teams outside of the AL East, such as the Padres, Phillies, or Rangers, that could enter the serious conversations.
You can also read some mock trades for Cease I wrote a few weeks ago here. Everyone will continue to keep an eye on this situation until Cease is eventually moved to a contending organization. Then, we can dive into the return prospect coming to Chicago.