Chicago White Sox struggle to attract top free agents as ownership hesitates to invest. Hopefully, new ownership in a few years will fix that. Until then, the organization still has to get better in other areas to also be a free agent destination.

Host Todd Welter highlights Jerry Reinsdorf’s resistance to baseball’s modern economics and explores how lacking multi-year deals and elite talent hurts the White Sox’s competitiveness. The episode analyzes Bleacher Report’s ranking of MLB teams as free agent destinations, discusses missed opportunities with players like Josh Naylor, and raises questions about the front office’s ability to build a winning culture. Insights on prospects Colson Montgomery, Kyle Teel, Braden Montgomery, and Hagen Smith in the Arizona Fall League add optimism for the future. Key topics include payroll challenges, player development, dysfunctional narratives around the franchise, and how the Dodgers and Cubs approach roster upgrades.

0:00 - White Sox Free Agent Destination

Host Todd Welter discusses what it would take for the White Sox to become a premier free agent landing spot, focusing on ownership, spending, organizational functionality, and market competitiveness.

10:03 - Josh Naylor & Sox Frustrations

Host Todd Welter reacts to Josh Naylor staying in Seattle, using it as a case study for ongoing White Sox free agency disappointments and larger organizational issues in team-building and payroll strategy.

21:11 - Arizona Fall League Prospects

Host Todd Welter reviews White Sox prospects’ performances in the Arizona Fall League, detailing standout players, future implications, and the importance (and limitations) of fall league success.

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