For the Chicago White Sox, the most important decision they are going to have to make this offseason is regarding trading Dylan Cease. As much as Chicago fans would love for the White Sox to keep him and try to return to relevance quickly, the reality is that this team is too flawed, has moved on from too many players already, and has too little payroll space (although that is self-imposed) to actually do that successfully. The White Sox may not want to call what is coming a rebuild, but that is what it is going to be yet again.
So far, the White Sox have been playing hard to get when it comes to Cease. They have talked a big game about not having to trade him and their rumored asking price for him is, well, very high to the point that substantive trade discussions have been a non-starter so far. However, no one realistically expects Chicago to hold that firm on that so the question becomes when will the White Sox finally rip the band-aid off and trade him?
The White Sox are playing a dangerous waiting game with Dylan Cease
The White Sox's logic here is fairly straightforward, if flawed. The front office believes that the longer they hold out in trade talks for Cease, the more desperate teams in need of pitching will become. To a certain extent, that could happen. There are going to be teams that miss out on Yoshinobu Yamamoto, Blake Snell, and Jordan Montgomery that will still be looking for quality starting pitching. Cease's two years of team control and upside is going to be very attractive to not only those teams, but also to teams that can't afford to play in the deep end of the free agency pool to begin with.
However, that goes both ways and waiting for top dollar could end up costing the White Sox. There are going to be teams that DO end up landing those top guys and others that will sign lesser, but still good, pitchers like Shota Imanaga, Michael Wacha, Seth Lugo, James Paxton, Lucas Giolito, and Marcus Stroman. Pitching is always going to be in demand, but teams are going to be looking for the best deal and getting strung along by Chris Getz and co. while other quality arms are going off the board doesn't have a ton of appeal at some point. Teams will only be so patient.
Of the top free agents, the next domino that needs to fall is Yoshinobu Yamamoto. He is starting to meet with teams stateside this week with clubs like the Mets, Yankees, Red Sox, Dodgers, and Giants all in on him. He probably isn't going to have to even sign to get the market moving. Once suitors start getting eliminated by his price or preferences, the starting pitching market could develop very quickly.
It would incredibly wise for the White Sox to start getting serious about Dylan Cease talks when that happens. It would put Cease right in the middle of the heart of the starting pitching market where the most of the motivated buyers are going to be active. They may not be able to clean out a team's farm system for him, but that was never going to happen. To get the best package for him, they need competition and urgency. If they wait too long, they could find themselves with neither.