Early in the rebuild, Theo referred to spending being related to revenue. Post-season was supposed to generate a lot of millions, which could cover season expenses and subsequent-year payroll.
Early in rebuild, they tended to save up, for later. (Tanaka story...)
More recently, Theo has tended to use future-year money for Nowacrat signings. (Heyward and Darvish signings both borrowed from the ensuing-year's discretionary spending.) I wonder if perhaps he did that again this past summer, with both the Kimbrel and Castellanos pickups? He hoped Kimbrel would get them into the playoffs and playoff-success would self-fund the contract?
Second, popular team superstars were supposed to generate lots of jersey revenue. When they were rising young stars, and we won the world series, I assume they made lots of sales. But now that they've got an 8th place team, I'm not sure that there have been lots of Russell/Rizzo/Bryant/Schwarber/Lester/Quintana jersey sales outside of the Chicago area?