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Future White Sox Roster Outlook Means The Time To Win Is Now

The White Sox are a few years away from a crossroads with the current roster. The time to win is now before some difficult decisions arise.
Rick Hahn Chicago White Sox GM Roster Payroll


The Chicago White Sox will soon approach a crossroads of expiring contracts, older age, and little help coming through the farm system or via free agency due to self-imposed financial constraints. Their time to win is now. I believe they have one of two decisions to make that will determine whether they extend their window of contention for the current core of players or go all-in for a championship over the next two years.

Let’s consider their willingness to move assets and what that White Sox roster would look like in 2024. We'll also look at how the team’s current payroll and ownership's willingness to spend impacts the future roster.

Win-Now Moves

At the 2021 trade deadline, the White Sox paid a steep price to address an important need when they traded Nick Madrigal to the Cubs for Craig Kimbrel. While this didn’t work out the way the Sox would have liked, it speaks volumes to the willingness of Rick Hahn and co. to move valuable assets needs. As a 38-year-old White Sox fan, I can say this trade was a big departure from what we’ve seen in past trade deadlines. It was the type of move that fans always wanted but never got!

If this is their strategy moving forward, we may see other notable assets -- such as Oscar Colas, Yoelqui Cespedes, Gavin Sheets, or Andrew Vaughn -- traded in an offseason or at the deadline. This may seem extreme, but not when considering the team’s current payroll and what the roster will look like in 2024 and after. It may be necessary to address roster needs to try to win a World Series in 2022 and 2023. If we take a look at what the roster will look like in 2024, things get a bit murky.

Potential Roster Departures

Jose Abreu: The franchise icon will be a 36-year-old free agent going into 2023. It wouldn’t come as a complete surprise if the club extends him for 2023 and 2024. However, I have a hard time seeing him in a White Sox uniform beyond that.

Yasmani Grandal: Yaz will become a free agent after 2023 at $18.25 million per year. I think he will see his days as a catcher come to a close. MLB finally adopting universal DH will give him a greater opportunity to extend his career, most likely with another team.

Lance Lynn: The big right-hander has been a workhorse his entire career and has an $18.5 million team option for 2024. The White Sox may be thinking about putting those financial resources elsewhere as innings continue to pile up on his arm.

Lucas Giolito: Giolito will see a big payday as a 2024 free agent. He will likely do so with another team unless Jerry Reinsdorf allows the front office to sign him to the largest contract in franchise history. Currently, Giolito and the Sox are haggling over $50K.

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Here are a few other players of note looking ahead to 2024:

  • Tim Anderson and Liam Hendriks have club options.
  • The newly acquired Kendall Graveman and recently re-signed Leury Garcia enter the final season of their respective three-year deals.
White Sox Payroll

Click here for the full Chicago White Sox Salary Breakdown Spreadsheet

The Payroll And Its Implications

In regards to payroll, the White Sox currently sit at seventh in MLB, per Spotrac. This is by far the highest payroll in franchise history, eclipsing last year's all-time franchise high. An additional investment via free agency before the 2022 campaign seems unlikely. Ownership has come a long way when it comes to spending with the payroll approaching $180 million. Now that the dust has settled on the lockout, we can see where owners throughout baseball stand in terms of spending.

Generally speaking, it created a long and contentious situation with the players and their union. The owners grudgingly agreed to spend additional money top to bottom on their major, minor, and international league rosters. If Michael Reinsdorf’s recent comments about the Bulls having to go above the NBA luxury tax limits to field a true title contender are true, then I find it very hard to believe that the Reinsdorf family will spend above those amounts for both teams.

What Should The Chicago White Sox Do?

The White Sox could consider a full-scale rebuild starting in 2024 with the remaining members of the team. Similar to what we saw in 2016-2017, they can parlay these players in trades for a group of prospects that build a new core of players. A rebuild could come regardless of the win-now strategy because of departures via free agency, possible retirements, and the few reinforcements left in the minors. Their best option in a rebuild would be to trade all or some of the remaining core players, such as Eloy Jimenez, Yoan Moncada, Dylan Cease, and Vaughn. The White Sox could see the prospect haul they did from the Chis Sale, Jose Quintana, and Adam Eaton trades.

A strategy to extend their contention window would be even trickier. The roster would contain a decent core of players, but the Sox would still have to extend those contracts. Additionally, the front office would have to fill some big roster holes with free agents. This strategy would be more feasible with a stockpile of minor league prospects ready to contribute. However, it simply doesn’t exist as the White Sox chose to trade away international spending money instead of using it to stockpile their affiliates with international talent.

This is why I believe that the time to win for the Chicago White Sox is 2022 and 2023. The possibility of extending their current window of contention exists but is tricky due to a lack of impactful minor league talent. A rebuild could take place, but with only a few assets to trade, it doesn’t seem as worthy to do so as it did in 2016. Such a scenario would leave fans and everyone around the league questioning whether or not the White Sox were ever truly committed to a full effort of building a champion.

My hope is that 2021’s trade deadline gave us a hint regarding how the front office plans to build a World Series winner. Therefore, I think they will do everything necessary to build a complete championship-caliber roster through trades from a front office now keen on moving their leftover minor and international league players of value.