This offseason presents new challenges to the Theo Epstein-led Cubs because, for the first time, the team’s status within their window of contention is unclear. From 2011-14, the Cubs were clearly rebuilding. From 2015-19 they were in a win-now mode. For 2020, they will need to address whether their current core is still good enough to compete.
Ultimately, that is not a question I can answer. I can, however, offer some useful information about how much money the Cubs have to address their problems via free agency. This is done by tracking their current payroll obligations and luxury tax situation, all of which is shown in this handy spreadsheet.