So, it probably doesnt absolutely have to start right away at the deadline, and it certainly doesn't need to happen all at once, but there is a certain extent to which Jed *must* begin spending some of this prospect currency over the next year.
Let's take the outfield where things are most crowded. The Cubs have 8 outfielders on the 40 man roster
- Happ, Suzuki, Bellinger, Tauchman as major league veterans. Bellinger has an opt out that looks 50/50ish today while the other three are definitely under contract for next year
- Canario and PCA on the Iowa shuttle. Canario is already on his last minor league option, so he basically has to get traded or permanently force his way onto the roster between now and next April
- Davis and Alcantara as (currently) pure minor leaguers. Both only have this year and next with minor league options, so the clock is ticking on them
- Owen Caissie has to be added to the 40 man this winter, and will begin burning options from there
1B is similar. You have Busch and Wisdom right there now, Bellinger and Caissie as options depending on how crowded the outfield is, a very strong argument to move Morel over there over the winter, and while he's got plenty of like roster administration runway Ballesteros is probably a 1B and probably not far off of MLB relevance.
You've gotta start cashing in some of these chips. Maybe Robert's not your choice but if you sit around waiting for perfect you risk burning through runway with guys like has already happened with Canario.