Skip to main content

White Sox Offseason Preparation: Now Is The Time

If the White Sox want to ascend from an upcoming team to a perennial contender, they need to shore up the roster with serviceable offseason acquisitions.
White Sox Offseason Plan

Photo: AP

I don't think I'm being hyperbolic when I say that this is the most pivotal four-month period for the Chicago White Sox organization since they stepped off the stage at the corner of LaSalle/Wacker on 10/28/05. The foundation of a championship core is in place, and several of those foundational pieces advanced their development during the 2020 season. Some of these pieces were just getting their first taste of the big leagues, but they held their own, paving the way for potentially significant jumps in performance beginning next season.

So here we are as a fan base, doing what we usually do, trying to play GM and conceptualizing what the organization should do to reach championship status. Let's be clear about something: the measuring stick has officially changed around here. You can list the flukiness of the 2020 season, the regionalized schedule, and expanded playoffs as reasons behind why the White Sox made the 2020 postseason, but they happened. From this moment forward, the expectation should be winning the American League Central and competing to win a World Series. I know those are lofty expectations for an organization with ten playoff appearances in its history, but anything less should be viewed as a failure in my eyes.

We now must confront a reality that has plagued the White Sox organization for over four decades, and one that is the greatest roadblock to this core group reaching its potential zenith. You know who I'm talking about, I don't even need to say his name. But it's the truth, plain and simple. He and he alone has the power to change the trajectory of this organization. We were told for years that when the time was right, the money would be there. Well, the time is right.

The White Sox are now a viable contender that needs the finishing pieces. They have a chance to grow the fan base both regionally and nationally at a time when the other team in town is at an organizational crossroads. South Side stars like Tim Anderson, Jose Abreu, and Lucas Giolito are garnering national attention. If this isn't the time, I don't know when it will be.

Yet, we are already getting smoke signals that it won't happen. Before this season even started, he who shall remain nameless started planting the seeds when his national media puppet, Bob Nightengale, put out a classic puff piece with this gem:

“I’m very worried about next year. I don’t know how much money we are going to lose. There are just so many unknowns. When we had the long layoffs in ’81 and ’94 [with baseball’s work stoppages], we had some idea it was going to end. And once it ended, we would be back to normal. We not only don’t when this will end, but when will normal come back?’’

- Jerry Reinsdorf, USA Today Interview on 7/15/20

Then we have the official Twitter account of the White Sox regional sports network putting out this propaganda:

Scroll to continue

Recommended Articles

So, it's very easy to see why there's a sizeable portion of the White Sox fan base raising concerns that the organization will not do what it takes to capitalize on this core group and the opportunity that has presented itself to be a true perennial championship contender. Simply put, he who shall remain nameless has done nothing to deserve the benefit of the doubt. I'm tired of excuses, and I don't want to hear about the huge losses the pandemic has caused, especially when this franchise has been sitting on money for several years after stripping down the payroll. I want nothing more in this world than to be wrong, but after the pathetic free agent "attempt" two winters ago, why should we believe this time will be different?

Truth be told, there aren't a lot of holes to patch on this roster. However, assembling a complete roster -- one that is devoid of black holes like Nicky Delmonico, Nomar Mazara, Reynaldo Lopez, and Carlos Rodon -- is paramount. If this team is truly serious about being a championship contender and trying to run roughshod over the Minnesota Twins (who recently set a North American sports record by losing their 18th consecutive postseason game, which you hate to see) and the Cleveland Indians, there are very apparent needs.

If I was in charge, assembling a roster of 26 competent Major League players would be the objective this winter. And in all honesty, it can be done without severely hampering the controlling owner's family trust in the long-term.

This team needs to acquire the following: two starting pitchers (or at least one that can serve in a swingman capacity making starts when needed), an actual right fielder, a backup catcher, two utility players, and two relievers (it could be one if Alex Colome is brought back). In reality, none of these will break the bank, given that the team will not be shopping at the top of the market (it would be nice, but it's not absolutely necessary).

Also, there's money coming off the books from the likes of Edwin Encarnacion (whose option will surely be declined), Carlos Rodon (who represents a major non-tender candidate), and James McCann's eventual departure. We know the Sox will be looking at mid-rotation arms to fill out the starting staff, so let's put the Trevor Bauer stuff to bed.

In recent years, we've seen teams expand payroll when entering their competitive window. If you look at teams that underwent extensive "rebuilds" once they broke through the .500 plateau, there have been sizeable increases in spending capacity. Teams like the 2015 Astros (33%), 2015 Cubs (43%), and 2010 Rangers (44%) all saw significant payroll increases once their competitive windows opened. A failure to do so this winter could result in the White Sox taking a step back and not capitalizing on their momentum.

Again, the Sox wouldn't even need to make any "major" free agent acquisition, they just need to avoid having replacement level players on the roster. An unwillingness to do so now would cause our greatest fears to be realized: one in which the organization was simply never serious about acting like a major market franchise and finishing the job.

If he who shall remain nameless chooses to continue down his frugal path, it will be incumbent upon Rick Hahn and Ken Williams to figure out how to improve this team given these constraints. Frankly, this is something they haven't shown an ability to do in recent years. Yet, if we are to have a true Soxtober in the coming years, they must find a way to get the job done.

Look, I'm tired of having to rehash this same column around this time every year. I know you're tired of reading it if I'm being honest. In the coming weeks, I'll be discussing potential targets and how I would construct this roster going forward, like many of you. This time needs to be different because if not now, when?