The Cubs front office has its hands full this offseason trying to reload the starting rotation while also reinvigorating an offense that struggled to consistently produce runs the past three summers. Ongoing ramifications from COVID-19 on planning for the 2021 roster will be huge as the Cubs don’t know when or how many fans they can have in the ballpark. Beyond what they’re able to spend in free agency, the financial situation will determine how they set up the 40-man roster as well.
As happens every winter, the Cubs will have until November 20 to reset their 40-man roster before the Rule 5 Draft, which is usually held at the winter meetings in early December.