How Should the White Sox Move Forward in Their Rebuild?

Ah yes, time to discuss the team on pace to be arguably the worst in the history of baseball. The Chicago White Sox are seeing things get even worse throughout the season with it becoming more challenging to see the light at the end of the tunnel.

With the trade deadline now in the past and less than two months remaining in the year, the attention has already shifted to 2025 in Chicago but there is still steps to be taken. With an improving farm system especially within the pitching side of development, the White Sox have some aspects to believe in, but this trade deadline was intended to enhance that drastically.

It’s hard right now to look beyond the historically bad product on the field that has lost 20 straight games, but at the end of the day this season was bound to be a lost cause.

Despite how painful it may seem, the purpose right now is developing a core in the next few seasons to create sustainable success.

The White Sox find themselves in a spot now with more clarity as to how the next year six months will go even if it’s not the ideal outcome to some.

Lack of Capitalizing at Deadline

The trade deadline came and went with Luis Robert and Garrett Crochet remaining on the White Sox roster for now. Regardless of the trades that were made, this result is going to inevitably feel disappointing given that these two were the only players on the roster capable of bringing in a true haul of young talent.

The White Sox did make four trades, with one being a larger scale three-deal deal and the others being simple one-for-one swaps of veterans for a prospect.

Erick Fedde was by far the largest chip the organization had to deal aside from the two aforementioned stars and he was sent to the Cardinals in a fascinating three-team deal. The White Sox also dealt Tommy Pham and Michael Kopech in this deal, a decision that seems odd given that Fedde and Kopech were likely the top assets they had to move.

The instant reaction to this deal around the baseball landscape was that the White Sox did not get enough value in Miguel Vargas, Jeral Perez, and Alexander Albertus in exchange for a pitcher who has been one of the steadiest in baseball.

In particular, it felt like the Cardinals got too good of a deal as they didn’t even have to include any prospects by sending Tommy Edman to the Dodgers in this trade.

I wrote a full trade return analysis piece that you can read further, but the reality is that this deal while underwhelming was not going to change the direction of the farm system even if one more prospect was included.

Other deals for veteran starters make this deal feel even worse for Chicago, but only time will tell if Miguel Vargas will breakout as an MLB regular or Jeral Perez will grow in a few years into a high-end piece.

When examining this deal from just six months ago, the White Sox turning a two-year deal with a pitcher coming back to MLB from Korea into three hopeful future pieces would be a huge win. I understand that he has elevated his value a lot this season, but this is a still a net positive for an organization in desperate need of young hitting talent.

Aside from an underwhelming Fedde deal, the White Sox did a nice job on deadline day turning three players that don’t factor into the future into three MiLB players.

Paul DeJong, in the midst of a sneaky solid season after signing a one-year deal, was flipped to the Royals in exchange for 22-year-old right-hander Jarold Rosado. He’s more of a flyer than anything as a relief pitcher, but Rosado has been great this year and should be ready for a promotion to High-A in the near future.

Tanner Banks has quietly been the best arm in a historically bad bullpen and they flipped him for a 2022 international signing in William Bergolla who signed with the Phillies for over $2 million. This is probably the best value pickup of the deadline as he’s just 19 years old and has flashed plus contact and speed in his second professional season.

The final deal was a surprise as the White Sox were able to offload Eloy Jimenez and his impending $3 million buyout for left-hander Triple-A reliever Trey McGough. It was time to move on from Jimenez and getting anything back is a plus. McGough should get innings out of the White Sox bullpen fairly soon as he’s been excellent all year in Norfolk.

Yes, this deadline feels like a letdown for a team that was expected to be a huge seller much like the Marlins and Rays ended up doing. But you can’t force deals that aren’t there and clearly there were not satisfactory offers on the table for the two stars.

It would have been ideal to move more veteran rental pieces, but there’s no reason to believe they didn’t try and the market just didn’t show any interest in those players.

Robert never felt likely to be dealt while Crochet’s market, which was already unique, took a turn last week upon his extension request and no team was willing to pay the huge asking price.

The fact is that judgement on this deadline truly does not matter as the system did get deeper, albeit not much better in terms of upside. The next eight months prior to 2025 will determine a lot more about the future direction than this deadline did.

Finishing 2024 Productively

It’s pretty tough to put a positive spin on the next two months, but there is ways that the White Sox can begin to inspire at least a bit of confidence. The record does not matter at this point even if it feels more painful as the losses rack up.

What does matter is beginning to establish pieces of the future ahead of what will be a pivotal offseason for the organization. Beyond just players, this team needs to find more elements of an identity that can lead to more success on the field and within the clubhouse.

Two key steps can be taken in August to at least try to be finish the year on a marginally better note than a franchise-worst losing streak.

The time has come for the Pedro Grifol era to end in Chicago. At the end of the day, this situation is not his fault as ownership and management is responsible largely for the roster he has been managing this season. With that said, he has not helped whatsoever and has not been the influence he was supposed to be in his two seasons with the Sox.

Turning a new core of young players over to a manager who has repeatedly claimed things that either don’t make sense or just are not the truth would be a mistake. Again, it may not make a huge difference this year, but there’s no reason for him to finish out the year rather than the team just moving out now after the deadline.

Part of moving on from Grifol the way I see it is that a new crop of talent can enter the organization without the presence of the past few years. This roster absolutely needs to be overhauled and it shouldn’t wait until the offseason if the organization actually cares about making progress.

For veteran players that were unable to get dealt at the deadline, waivers should be on the horizon. The same goes for veterans on the roster who have simply have not performed at a MLB level. The next few months are about testing the prospects who have been performing at the upper levels.

A handful of players, particularly most of the bullpen, should be let go of one way or another in the coming weeks. These spots should all be handed to a variety of prospects who can attempt to prove themselves heading into 2025. The majority of the bullpen should be rookies down the stretch.

Beyond just the bullpen being cleared out, veteran players should be let loose or take a back seat to more young talents. Chris Flexen’s rotation spot should go to one of the many prospects in Charlotte. Another young starter should take on a piggyback role behind Garrett Crochet’s limited inning starts.

Ky Bush, after posting a 2.12 ERA in Double-A this year, has already been called up and others should follow. Sean Burke, Jake Eder and Mason Adams, all deserve MLB innings as soon as possible as well.

The priority for the rest of this year has to be the future. Players like newly-acquired Miguel Vargas, Lenyn Sosa, Brooks Baldwin, and others need everyday innings to see what they can provide. Bryan Ramos should get another shot at the MLB level down the stretch with his recent hot streak in Triple-A as well.

Essentially, it’s time to stop wasting time. Even if you want to maintain another year of control for many of these promising players, they can still get maintain that while getting some MLB innings. Trying to plan for the future truly this offseason will be much easier if a few young players prove their value in the next two months.

Beyond this year, the organization faces a pivotal offseason that will play a larger role in the future of the organization.

Offseason and Beyond

With Luis Robert and Garrett Crochet still under contract for three years and two years, respectively, the team has time to make franchise altering moves that were expected at the deadline. This offseason then becomes incredible crucial to getting this organization back on track.

While trading those two due to the market felt smart, the market will expand greatly come this winter. While huge market franchises are usually the ones capable of swinging deadline blockbusters, a variety of emerging young teams could join the sweepstakes for these two.

This will allow Chicago to ideally maximize the trade returns.

Taking a look at the outfield landscape around baseball, a number of teams could be very intrigued by the idea of adding Robert for three seasons especially if he produces a little more down the stretch. Beyond the initial teams that will show clear interest such as the Phillies, Mariners, and Dodgers, others should emerge.

The Pirates, Royals, Cubs, and Mets fit the bill as teams preparing to contend in 2025 with a need for some additional offensive juice. With strong farm systems, the two NL Central clubs would make a ton of sense.

At the very least, these smaller market teams will give the Sox a shot to drive the price up when negotiating with the favorites to land Robert.

For Crochet, any team with some level of risk tolerance trying to compete the next pair of seasons will be calling up Chris Getz. The Dodgers and Orioles have long seemed like the best fits for the left-hander but others like the Brewers, Red Sox, Padres, Cardinals, and Mets will have more time to work on a deal.

Assuming he remains healthy the rest of this season, Crochet’s market should be vast with potentially a double digit amount of teams interested in the emerging star. His arm comes with risk, but the extension request will not be relevant come the winter and his market will undoubtably be robust.

Nailing the trades for these two is so much more important than anything else on the horizon for a front office that has to not only prove themselves but build upon a strong, albeit incomplete, farm system. Lacking elite upside bats but loaded with arms, the White Sox could have one of, if not the, best farm in MLB if they can acquire four or five high-end bats by trading these two.

Aside from cashing in on two elite pieces, other steps need to be taken for this team to be at all competitive and at least show positive signs in 2025.

Under the assumption Robert is traded, which feels likely, the White Sox will have a grand total of two non-arbitration players under contract for a total amount of $23.1 million.

When factoring in arbitration throughout the roster for young players, the White Sox should have no more than $40 million on the books for 2025. Leaning into the young core is important but the organization and particularly owner Jerry Reinsdorf will have to shell out some contracts this winter.

Via Spotrac:

One of the mistakes of the previous White Sox rebuild was failing to put the proper surrounding pieces around the core of young talent. While this team is not ready to contend any time soon, bringing in a few truly impactful players to surround what will be an extremely young 2025 roster is consequential.

On the pitching side, there won’t be a huge need for many additions. Maybe a true closer could make sense to help ease the stress on a bullpen filled with rookies. Possibly adding an experienced starter to fill Crochet’s spot too.

The biggest need in free agency will be some hitters though. This team absolutely needs to at least a pair of impact bats that can provide a layer of protection. Many prospects including shortstop Colson Montgomery and catcher Edgar Quero will have a real shot to crack the Opening Day lineup and remain there all season.

At the very least, the White Sox need to acquire a starting outfielder (whether it be in center to replace Robert or to fill the void in right) and a corner infielder to help this offense.

Going all in on the future starts with the trading of Robert and Crochet, but it has to continue with adding some degree of talent. Even in a rebuild, this team has so much financial flexibility in comparison to a payroll that was near $200 million just two years ago. They won’t spend nearly that much on a rebuilding club, but they can afford at least four or five additions in the offseason.

Final Outlook

The White Sox are at least two years away from being a competitive team. That does not mean that there is not a ton of work to be done and progress to be made despite how dark things currently feel.

Adding more talent, prioritizing the young talent already possessed, and establishing a new staff capable of developing said talent is the only way to proceed. The upcoming offseason will determine a lot about this rebuild and will truly show if Chris Getz and company are capable of leading this franchise.

Buckle in White Sox fans. It’s gonna take some time but there’s always a path, folks.