White Sox currently focused on a rebuild, but it’s unclear whether they’ll find offers acceptable to them for Chris Sale, Jose Abreu, etc.

— Buster Olney (@Buster_ESPN) November 14, 2016

This decision is questionable at the very least, but it’s the direction in which the front office seems confident. One of, if the not the most important part of a White Sox rebuild is trading Chris Sale.

Rather than fielding a competitive roster around Sale for the past five seasons, the White Sox have found themselves “mired in mediocrity” thanks to a refusal to spend at the right times and an inability to identify the right players to spend on. Now that the Sox are look ready to rebuild, and the best and most decisive way to start that process is to dangle their ace in front of the market and sell him to the highest bidder.

The 27-year-old lefty has three more years left of team control and has finished in the top six of AL Cy Young voting in every year he worked as starter, and is likely to do so again in 2016. Simply put, a pitcher of Sale’s caliber at a team-friendly price (he can earn up to $38 million over the next three seasons) is hard to come by.

When searching for precedent of a trade of a pitcher with Sale’s resume, low cost contract, and years of team control, I came up mostly empty. The closest trade of recent vintage is when the Kansas City Royals traded Zack Greinke to the Milwaukee Brewers for Lorenzo Cain, Alcides Escobar, Jeremy Jeffress and Jake Odorizzi before the 2011 season. Greinke had two years remaining on his contract, an AL Cy Young award on his resume, and was headed into his age-27 season.

The Greinke trade was instrumental in the Royals rebuild, which ultimately led to two-straight World Series appearances and one championship, but it did not start the process by itself. At the time of the Greinke trade, the Royals were already deep into the process of building their new core, and had Mike Moustakas and Eric Hosmer in the organization and nearly major league ready. Even after the infusion of major league ready talent, the Royals’ World Series Championship was not until five years after the trade; not a long wait, but slower and more typical than the Cubs’ accelerated ascent to the top of the league

If the White Sox were to follow a similar timeline, Jose Quintana, Jose Abreu, and Adam Eaton would all be gone from the team (assuming they don’t extend or re-sign) by the time their new acquisitions are at their peaks. Most additions made from a Sale trade would arrive and begin making an impact just as the rest of the current core was on its way out or in decline. As valuable as Sale is, trading him alone wouldn’t provide the Sox with a whole new core. It would place the White Sox in a similar position to where they are now: a several really good players, surrounded by insufficient depth, and what they gain in long-term assets and ceiling they would forfeit in immediate star power and production from a single roster spot.

That brings us to the next issue with a Chris Sale trade: finding a team willing to pay the right price. For the sake of comparison, in the Greinke trade the Royals received two of the Brewers’ best position prospects, their best pitching prospect, and a throw-in. Sale should theoretically be worth more than that because of another whole year of team control at a lower salary.

Teams that can trade that much talent without directly eliminating their chances to reach the postseason in the next season–and the strongest reason to acquire Sale would be the firm up a postseason contender–aren’t very common. Currently the teams that best fit the bill are the Dodgers and Red Sox, with the Rangers also a possibility. All three would love to add a top-end starter to take them to a whole new level, and all three of those teams also have prospects ready to make a major league impact in the next few years. But while this appears to make the White Sox and each team clear trade partners, problems are bound to arise when meaningful discussions actually begin.

The Red Sox, Dodgers, and Texas all have their own set of “untouchable” prospects they intend to shield from any trade discussion. Unsurprisingly, those prospects are the best ones in their respective systems. All signs and reports hint of a wide gap between the White Sox demand and what teams are willing to give. In other words, if the White Sox really want to trade Sale this offseason and begin their rebuild, they will need to prepare for a lengthy negotiation process to shake loose tightly-held assets, or for the sake of expediting the deal, they’re going to have to trade him for less than he’s truly worth. Lopsided trades happen all the time, of course, but starting a multi-year rebuild by getting owned in a trade for your best asset doesn’t exactly inspire confidence in the merits of the process.

Keeping Sale does not seem like a better option in a full rebuild. He’s the greatest asset on the team and if they sell away everyone but him, he spends another three seasons on a squad with an inability to win games. If they continue refuse to buy to add to the roster, he remains a star on a team with no purpose. It’s understandable to want the Sox to pick a direction, since sitting in the middle provides no hope for the future and only offers failure in the present. But selling away Sale at this moment is a careful process that could lead to a mistake if rushed. With his price as high as it is, it’s still tempting to consider giving Sale one more shot to win in a White Sox uniform by spending a small amount of money to improve the roster, but the Sox are simply unwilling to take that step.

In science, the second law of thermodynamics says that the universe is always moving towards increased disorder and chaos. Some call that Murphy’s Law, which often gets simplified into ‘anything bad that can happen, eventually will.’ With the misfortune they have found in their moves in recent years, the White Sox seem to be ruled by their own version of this universal law, which only heightens concern on how they approach this, the franchise’s most important trade of the next decade.

Lead Image Credit: Steve Mitchell // USA Today Sports Images