I think when we eventually look back at the jed years, and this probably has as much to do with the Ricketts honestly, it's the timidity that really held us back.
Not to relitigate an offseason half a decade ago, but man it's hard to look at that Harper deal and not feel like signing him would have wildly changed the trajectory of how the team has been built since. Talent coalesces around stars, and all of these offseasons of swings and misses since then would have been so much different.
But anyway, Jed (or tom i guess, who knows. probably both) was too scared of that relatively paltry commitment. All the other Harper level stars since (this is my opinion but i think it's right) were never interested in chicago because by the time they hit the market, our Harperless roster looked pretty thin and there were clubs with better orgs, better ownership, better rosters and more money. Easy choice to make.
But anyway the timidity really has limited us in other ways too. It's easy to say "sign harper duh" but a lot of us have said the same thing about other FAs since whose deals do not look as appeaing anymore. For every "sign Harper" there was a "sign boegaerts" or "sign correa" (i did both I believe.) Looking back, we really came out OK on the SS market that year. Swanson is solid, still young, fits our team identity and isn't overly expensive. Hard to argue against that. But the point of a deal like that is to create flexibility to take a big swing elsewhere. But of course we didn't do that. Every offseason is full of these half-measures and "maybe you can squint and this guy runs into a 3 war season" signings and it's just not enough.