Everyone knows the Cubs are a sinking ship. Tom Ricketts continues to declare "biblical" losses during the 2020 season. Theo Epstein could not part the sea of red ink. So Theo decided to bail; he cut a deal where his friend, Jed Hoyer, would retain his job with the new President title. The move saves Ricketts $10 million in Theo's 2021 salary. (The Athletic reported that recently the Cubs laid off 100 employees which we assume does not count the scouting and minor league staff let go early in the year.)
The Cubs are still a highly leveraged (debtor) team. The Ricketts family is also highly leveraged due to their overbuilding around Wrigley Field. The pandemic crushed their real estate holdings as many tenants, including Joe Maddon's restaurant, went out of business. Tom Ricketts had convinced his parents that the Cubs were a money making machine even in bad times (under the Tribune ownership).
But the Cubs bowing out early in the playoffs since the World Championship has hurt the club, both financially and structurally. Theo and Jed put all their eggs in early first round (can't miss) prospects like Bryant, Schwarber, Almora and Happ while overpaying for free agents to fill roster gaps (especially in pitching.)
Since 2016, the team core (Bryant, Rizzo, Baez, Contreras and Schwarber) have not lived up to high expectations. Instead of a dynasty, the Cubs gained one World Championship (which was a generational accomplishment not to be dismissed in their legacy). But as 2021 is around the corner, the cupboard is bare.
Three fifths of the starting rotation is gone to free agency. The core of Bryant, Baez, Rizzo and Schwarber are in their final contract years. The Cubs minor league system is devoid of any major prospects. The system ranked 26th with Nico Hoerner the only Top 100 prospect.
2021 appears heading toward a "crash and burn" season. The pundits believe the Cubs should trade their pending free agents to get something for them (other than a compensation draft pick). But others note that those players are coming off bad seasons so they have little trade value. A few writers even speculated that the Cubs could non-tender Schwarber to save his projected $8 million arbitration award. No team is going to take Bryant and his $18.5 million projected salary as a rental player, especially with his injury history and poor 2020 stats.
The only players with real trade value are Darvish and Hendricks. But Hoyer cannot be insane to trade away his remaining starters for prospects. Internal candidates to fill the rotation are Mills, Alzolay and Rea. Ian Happ was the only player to show a break out potential to other clubs. But trading Happ leaves Almora the sole center field candidate.
Even though money came off the books (Lester, Chatwood, Quintana), that money appears to be lost in 2021 as Ricketts clearly indicated that the payroll must come down substantially. As of today, there is not one AAA player who projects to be a starting MLB player.
Another problem is that the fan base may not support another complete tear-down rebuild. The Cubs were good enough in a bad division to have middle round draft picks but it will be more hit and miss since the scouting department was gutted in 2020. Player development has always been an issue for this team. Hoyer indicated that he may rely more on advanced stats than scouting eyes. But that has been the problem with stat overload on major league players (and a rotation of coaches preaching new approaches).
The Epstein era had the Worst of Times and the Best of Times and now fades back to the Worst of Times. For diehard Cub fans, the White Sox resurgence with young, exciting players, is going to be bitter pill to swallow as the Cubs begin to wallow.