The White Sox haven’t said anything concrete towards their plans towards the offseason, and why would they, but there is reason to believe they are entertaining selling off prized assets to help build the next core. With a third of the starting lineup (Melky Cabrera, Todd Frazier and Brett Lawrie) playing on contracts that expire after 2017, the White Sox have more holes coming on top of the depth they are already lacking. The composition of the roster gives credence to the idea that a good deal of roster turnover is inevitable and the team has rationale to aim to get younger. Whether it is this offseason or the next, the White Sox hand is essentially forced to scale back for future years at some point over the next 18 months. Given they still have a stable, albeit flawed, roster, they could move to re-up one more time and try to win with this core before the window of competition shuts entirely.

When Rick Hahn spoke to the media in July and told them that the organization was “mired in mediocrity” one thing became clear. The obvious thing being that the White Sox were unlikely to compete for a playoff spot in 2016, but past that, it was clear that Hahn and the rest of the front office had plenty of work to do behind the scenes. This work didn’t result in a flurry of moves before the deadline to the dismay of fans, but it was sure to yield valued due diligence regardless. Past that, there’s value that White Sox didn’t tip their hand. As the roster sits, they can go either way. In their activity testing the market, the White Sox spoke to at least the Red Sox, Dodgers, Rangers and Yankees and gauged the value of players including and not limited to Chris Sale, Jose Quintana, David Robertson and Todd Frazier. This time period also gave other teams opportunities to scout the White Sox players such as when Bruce Levine reported the Red Sox sent Frank Wren to watch Sale.

While it’s never publicized for understandable reasons, front offices will remain in contact for more than just waiver deals past July. Teams are often laying groundwork of deals, gaining an understanding of what a given team would be willing to offer for a given player and familiarizing themselves with other farm systems. GM Rick Hahn spoke candidly after acquiring Jeff Samardzija about his email exchanges prior to the Winter Meetings with now Athletics GM David Forst that ultimately made way for the 2014 trade. As I reported in 2015, the Cincinnati Reds and the White Sox were talking about a potential Todd Frazier and his cost as the 2015 season dwindled away.

Hearing from all over that the #WhiteSox are expected to make a big play for #Reds third baseman Todd Frazier this offseason. — Brian Bilek (@BrianBilek_) October 4, 2015

So it’s fair to say that the White Sox front office has gathered an equitable cache of information on players they may or may not move. As has been reported multiple times, the team claims that their first “big move” will make it very clear which direction the club will go in 2017 and it’s possible, while I am assuming, they’re still not sure which way that is. With a capable roster headed up by cost-effective, premier talent, the team has the upper hand in negotiations. By no means do they have to trade Chris Sale or Jose Quintana or any of their assets this offseason. While it comes with a nonzero factor of risk, they don’t have to trade the likes of Todd Frazier, Melky Cabrera, Brett Lawrie and David Robertson as they could move these players midseason.

Instead, the White Sox can let the market play out and survey the field as the surefire contenders in need of additions are subjected to a free agent class that is the worst of recent memory. As far as the starting pitching in this free agent class, I’ll go ahead and say it is the worst in recent memory. Past the resurfaced and reconstructed Rich Hill, who is entering his age 37 season, competitors will compete for the likes of Andrew Casher, Edinson Volquez and Jeremy Hellickson to bolster their rotations - hardly the best gang of arms to sift through and feel comfortable about the upcoming 162 game season.

As previously mentioned, the White Sox will scale back and get younger either this offseason or next. That’s not my opinion or my hopes for the club, that is what the current roster construction and the accompanying contracts force on the hands of those who head up baseball operations. It is my opinion that the White Sox enter the offseason with great flexibility. However, it could complicate things if the White Sox were to add this offseason as any long-term cash outlays come with ample risk for a team that could be on the verge of a rebuild. So if this offseason develops with the White Sox pushing for 2017, they’re hamstrung by the added risk of adding a long-term contract to a roster on the verge of a pivot year and the signing of any compensation-attached free agent would have them lose one of the most valuable unprotected draft slots in the Rule 4 Draft.

So after the World Series comes to an end, the team will establish organizational plans at the team meetings in Glendale, they will gather more due diligence at the General Manager Meetings in November and then ultimately makes franchise-altering moves at the Winter Meetings in December. Of course nobody would be shocked to see a baseball operations team headed up by Kenny Williams “retool” and try to crack the playoffs next year. That being said, the White Sox will come to the league functions that turn on the offseason hot stove with pocket aces against a flop that offers nothing of value.

It is no secret to anyone that follows the White Sox that the team has two of the most productive and most valuable pitchers in the game Chris Sale and Jose Quintana. Whether they trade one, neither or both, they will continue to talk about the possibility as they already have in the past. When other teams’ executives drum up their potential offseason plans they will lay out their respective target lists, run their projections modules and ponder the potential outcomes of their offseason activities. Perhaps, some thoughts could be “Who would throw Game 2 of the playoff series after Sale throws Game 1?” or “What contingencies do we have in place if Andrew Cashner pitches himself off the playoff roster?” or “What free agents can we add with the flexibility of our ace getting paid like a fourth starter?”

So whether you’re someone who wants to sell everything and field a team of 22-year-olds or if you think it’s a sin to not try and compete with the current core, your wishes are subject to this market. When the executives come to dance in hopes of building a future champion, the White Sox will come with the biggest briefcase of solutions to other teams’ problems. For teams in need of elite starting pitching (i.e. everyone), the White Sox have two to choose from and they’re both on entirely team-friendly contracts.

In essence, I believe the White Sox offseason and their course of actions is to be determined by the league’s offers for the team’s two prized left-handers. It has been leaked out that the White Sox are looking for five players in return and the team would want major league players as well as prospects included in the mix. It could be assumed that of those five pieces, the White Sox would like a headliner that is a slam dunk to be a pre-arbitration, productive MLB player. Frankly, there are only several teams who have the headliners and supporting pieces to meet these demands. If Dave Dombrowski isn’t willing to give up Andrew Benintendi for Chris Sale or if Jon Daniels’ best headlining piece for Jose Quintana is Joey Gallo then the White Sox can move on and look towards finding a center-fielder and a catcher.

For an organization facing annual disappointments, the White Sox enter this offseason with a great dark cloud over their heads. Despite the upper hand in the negotiations, the White Sox are coming to a pivot point in the next year-and-a-half. With an owner in his 80’s who has no wishes of signing on for a scorch-the-earth rebuild and a roster that begs action one way or the other, the White Sox need to have the optimal outcome this offseason. Trading a Sale or Quintana, and in turn, some of their teammates, could jumpstart a rebuild for the organization. It could bring them a gaggle of talent to complement the talent they already have the rights to. If the right deal is out there, they must pounce and accelerate a rebuild before their premier assets have their value expire or worse, get injured. If the right deal is not out there, the front office has to fill the holes at bay and accumulate the depth that could give Sale/Quintana a chance to do their best imitation of Randy Johnson and Curt Schilling in October of 2001. Given the string of failures to compete and an inevitable pivot year looming, the White Sox course of action has an even larger effect on the years to come.