They should absolutely not blow it up, but if they did I think they could probably clean the slate and fully stock the farm. There's only 4 guys with guaranteed money beyond 2020: - Heyward - Darvish - Kyle - Kimbrel Heyward's contract is way underwater, but now down to four years left he's probably dealable if you ate ~half. Kimbrel's contract looks bad right now, but I think the industry is willing to give him benefit of the doubt for last year. If he had a good first half he'd be valuable again by July. Darvish and Kyle have positive value (Darvish a little, Kyle a lot). From there looking at trades, it would look a lot like when the White Sox blew it up. I would guess Javy would bring back something akin to the Quintana deal, and Bryant a little less than that. Willson and Rizzo would each net a top 100 guy plus another prospect or two of note, and Schwarber a couple guys in that "just missed" area. All together that's probably a #1 farm and and basically clean books after 2020. That being said I still wouldn't do it. If Theo deals KB and Willson, the Cubs are probably the slight Central favorites in 2020 with a top ~10 farm and Heyward as the only really bad money on the books. A disappointing place to be, but still a pretty good one all things considered. Much better than signing up for 2-3 years of horsefeathers ball IMO.