As Major League Baseball’s trade deadline approaches next Monday, the focus intensifies on the roles of Jerry Reinsdorf and Tom Ricketts, chairmen of the Chicago White Sox and Chicago Cubs respectively, who ultimately hold the authority over their teams’ strategies and spending decisions. Both clubs are in playoff contention but face pressing needs in their pitching staffs, while their ownership’s willingness to invest heavily remains a topic of debate among fans and analysts.

While team presidents and general managers—Jed Hoyer for the Cubs and Chris Getz for the White Sox—handle day-to-day roster moves, the final approval for major acquisitions rests with Reinsdorf and Ricketts. Historically, they have exercised restraint in committing to high-cost contracts. Reinsdorf, 90, has never handed out nine-figure deals, and Ricketts has avoided paying luxury tax penalties, reflecting their cautious approach to financial risk despite their teams’ ambitions.

The Cubs entered the offseason seeking to contend in 2026, signing free agent Alex Bregman to a five-year, $175 million contract, and currently carry a payroll of approximately $233 million, the eighth-highest in MLB. Their spending exceeds most divisional rivals but remains below the levels of teams like the Los Angeles Dodgers, New York Mets, and New York Yankees. Ricketts has emphasized the club’s goal of breaking even financially, though he later softened that characterization.

Despite this, the team’s pitching depth remains a concern following the recent designation for assignment of starter Jameson Taillon. The Cubs may need to acquire multiple arms at the deadline given the ongoing struggles within their rotation. However, last year’s trade activities did not yield substantial improvements, leading to questions about how aggressive the front office will be this time around.

On the other hand, the White Sox operate with a markedly leaner payroll, ranking 28th in MLB at roughly $90.7 million, significantly below divisional rivals like the Cleveland Guardians. Reinsdorf has preferred building through the farm system rather than relying heavily on free-agent signings, a strategy that contributed to the team’s previous rebuild efforts. That approach saw top starting pitchers such as Garrett Crochet, Dylan Cease, Chris Sale, and Carlos Rodón depart due to the organization’s reluctance to commit to long-term, high-value contracts.

Reinsdorf, whose succession plan envisions billionaire Justin Ishbia assuming ownership between 2029 and 2034, is reportedly eager to end his tenure with a winning campaign. The White Sox have recently made moves to strengthen their roster, including acquiring starter Jose Urquidy, but whether the chairman will authorize significant expenditure to secure a frontline pitcher remains uncertain. Fans and insiders recognize the pressure on Reinsdorf to balance fiscal prudence with competitive urgency, especially with labor agreements and future rebuilding risks looming.

Reflecting on past decisions, Reinsdorf acknowledged the challenge of rebuilding while managing his advancing age, stressing the responsibility of prioritizing fans’ interests over personal considerations. Since the team’s previous rebuild culminated in a playoff appearance in 2021 before regressing, the current season—coupled with promising young talents like Munetaka Murakami and Colson Montgomery—could represent a pivotal opportunity.

With time running short and both the White Sox and Cubs striving to capitalize on their competitive windows, the forthcoming trade deadline will test how far Reinsdorf and Ricketts are willing to leverage their financial resources to position their franchises for postseason success.