5 questions for White Sox to address this offseason 

This story was excerpted from Scott Merkin's White Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

CHICAGO -- This week’s newsletter focuses on five questions the White Sox will have to address as the Hot Stove soon turns up from its current simmer and moves toward the 2024 season.

But one question White Sox fans might be considering, which is a little early to address, centers around the 2023 World Series. The American League champion Rangers are two years removed from 102 losses and one year past a 68-94 showing, while the National League champion Diamondbacks dropped 110 as recently as ’21 and finished with a 74-88 record in ’22.

So, could the White Sox travel that same path, coming off a 61-101 showing? Josh Barfield, the team’s assistant general manager who worked the past nine seasons with Arizona, believes anything is possible.

“We have a bunch of talent already on this roster,” Barfield told me in a recent interview. “If we do things right, if things work out, there is a scenario where we can add and look to continue to build to grow toward the future but also in the short term be in the mix as well.”

Let’s take a look at those five early questions facing the White Sox:

1. Is this a rebuild or a retool?
From what I can discern, a rebuild is considered a total teardown of the roster last undertaken by then-general manager Rick Hahn and executive vice president Ken Williams during the 2016 offseason. It began with the trade of Chris Sale to Boston.

That direction doesn’t appear to be favored by general manager Chris Getz. The White Sox are focused on retooling with a solid talent base still in place, but they could take a slight step back in 2024 to better the future while holding out hope for competing in the AL Central. Playing in the AL Central can be viewed as a bit of a crutch for Chicago, but it always gives the club hope.

2. What is Tim Anderson’s future?
I remember speaking to Anderson back in February in Glendale, Ariz., as he prepared for the White Sox season and the World Baseball Classic with Team USA, about being in line for another high-money multi-year shortstop deal. Today, the talk surrounds whether the White Sox will pick up Anderson’s $14 million club option for 2024 or use his $1 million buyout. It was that type of uncharacteristically rough year for Anderson.

My bet is on a bounceback season for Anderson after an early-season injury derailed him in 2023. I also think that bounceback will come with the White Sox, who probably aren’t giving up Anderson for nothing. In our conversation one day before the end of the regular season, Anderson expressed a willingness to play second base as well as shortstop. That versatility should help the 30-year-old, who still drives this team when he's on point.

“Now I get an opportunity to dig in and get back to work, get back in the lab,” said Anderson, who admitted it was tough to implement in-season changes with games every day. “Get the body right. Get back to a point to where the consistency is day to day.”

3. Where’s the pitching?
Here are the White Sox certainties in the starting rotation five days before Halloween: Dylan Cease and Michael Kopech. There are young hurlers on the rise, such as Nick Nastrini and Cristian Mena, but they most likely won’t be ready to break camp. So, Getz and his front office have to not just build this starting five, six or seven, but the entire staff.

4. Will the core change?
There’s already been talk about the White Sox being a more “dynamic” team offensively, defensively and with their baserunning in 2024, and the current roster is not exactly built for that style of play across the board. It’s not a shot at the players who currently make up the team, but their skillsets check different boxes. Chicago will explore all avenues to make this team better, which makes nobody untradeable.

5. Can Luis Robert Jr. top his ’23 showing?
OK, the All-Star White Sox centerfielder is as close to untouchable as anyone on the roster. He’s shown extended glimpses of his five-tool talent prior to the 2023 season, but with 38 homers, 36 doubles, 20 stolen bases, an .857 OPS, a career-high 145 games played and a Gold Glove Award nomination, Robert Jr. proved to be one of the game’s best players. He’s a game-changer, and the White Sox next contender should be built around his presence.