What happened: Major League Baseball's 2026-27 offseason is underway, initiating the winter roster-building period. Front offices are finalizing their initial trade discussions and preparing contract evaluations ahead of open market activity.

Why it matters: The upcoming market tests organizational spending strategies and financial frameworks across clubs. Roster adjustments will reshape franchise depth and payroll flexibility ahead of spring training.

What to watch: Eligible free agents can officially begin negotiating and signing contracts with any team on Nov. 3.