Chicago Cubs: 3 questions we must ask after a historically bad week

When will we see the “Next Great Chicago Cubs Team?”

The answer to this sure depends on who you ask. I think an even better way to ask this question is this, “What will we see first – the Cubs in the postseason or the opening of the sportsbook?”

There is a lot of uncertainty going into the end of this season that will undoubtedly carry into the offseason. Jed Hoyer has gone on record saying he doesn’t even know what they are going to do. But he’s also on record saying that trading away the core was not the beginning of a rebuild, but rather the beginning of a re-tooling.

Will the Cubs be competitive in 2022? I have no idea. No one has a clue, including Hoyer and the rest of the front office.

When will we know? I think we will know when free agents start to come off the board and there is resolution to the new impending collective bargaining agreement. This could go well beyond Winter Meetings, and some writers have even gone on record hinting at a work stoppage/strike-shortened season.

I think if I were to ask Hoyer this, the answer to it would be very vague and generic. Something like “soon,” or “we have the pieces in place to be successful.” Really anything that could be said to answer the question without actually answering the question.

I do think for the next great Cubs team to be constructed, external pieces are going to need to be brought in, especially starting pitching. It really is all going to come down to how much Sir Tom Ricketts allows Hoyer to spend on players.