2020 has been an intriguing year for Jerry Reinsdorf as the owner of both the Chicago White Sox and Chicago Bulls. Reinsdorf was pivotal in finally changing the Bulls front office and hiring Arturas Karnisovas to spearhead the basketball rebuild. For the White Sox, the team is once again competitive after rebuilding for the last three seasons. With the projected success of the White Sox going forward, it is recent moves made by Reinsdorf that could lead to him hindering the team’s potential success in the future.

On Thursday, the Bulls finalized a decision to keep embattled head coach Jim Boylen due to financial concern as if the team were to fire him, they would have to pay him and a new head coach. Due to the financial losses that MLB owners have been concerned about throughout this summer and with the possibility of an MLB lockout in 2022, this could lead to Reinsdorf restricting the White Sox’s ability to spend on top-tier free agents in the future.

Although the team spent this previous offseason to sign pitcher Dallas Keuchel, catcher Yasmani Grandal, and designated hitter Edwin Encarnacion, the team has been notorious in not big money on free agents. Where fans have developed a mindset that the White Sox are reluctant to spend money, their beliefs were justified in the offseason before the 2019 season.

During the offseason, All-Stars Manny Machado and Bryce Harper were both free agents and were requesting 300 million dollar contracts. The White Sox were in pursuit of both players because, at the time, they had the second-lowest payroll in all of baseball and could afford a large contract. It was a move that many felt the White Sox needed to make to show how serious they were in becoming competitive once again. Chicago would fail to sign either player as Harper signed with Philadelphia, and Machado would sign with San Diego. White Sox fans were livid that the team allowed San Diego to outbid them for the services of Gold Glove third baseman, especially when the deal fell through due to incentives for the last year of the contract.

The team made amends this past offseason with using the money to acquire the veteran free agents and extend some of their core players in Yoan Moncada and Luis Robert. The worry going forward comes if and when the team needs to add a premium hitter, or more importantly, a top of the rotation pitcher. Chicago did try to sign former Mets pitcher Zach Wheeler to the first 100 million dollar contract in team history offering the most money. Wheeler chose to sign with Philadelphia due to proximity to his family. The question now is if an ace pitcher is available on the market, will Reinsdorf allow the White Sox to spend the money?

No matter how the 2020 season ends for the White Sox, they will need to add starting pitching depth as two of their starters are currently on the injury list. Reynaldo Lopez and Carlos Rodon are out with shoulder soreness, but both will be back in a few weeks. Rodon is a free agent at the end of the year, and Lopez could be moved to the bullpen if he doesn’t demonstrate an ability to be consistent. Over the next few offseasons, Chicago will have a chance to spend on premiere pitchers include Trevor Bauer and Noah Syndergaard, if they don’t sign contract extensions.

The concern now is whether the team is open to spending over 150 million for over five seasons as free agent starting pitchers have requested those numbers in prior years. If Chicago is an All-Star pitcher away from a World Series, will Reinsdorf allow general manager Rick Hahn to make the costly expenditure knowing they might not get their full return on investment?

Given the unknown long-term financial ramifications of the pandemic on pro sports teams and the looming work stoppage, Reinsdorf could be in a position to save rather than spend. It would be another costly decision, not financially, but from a trust standpoint with fans. White Sox fans, although entertained by young core the team will have through 2026, will still wonder why the team owner is reluctant to go all in to give his team the best chance at winning a World Series.

Steve Pusch
Eastern Illinois University graduate, Steve earned a Bachelor’s in Journalism with a concentration in sports. While at EIU, Steve co-hosted a weekly radio sports talk show focused on Chicago.