In 2014, we may have had three to four guys in the top 10,

Depends how you look at it I suppose. Pre-2014, both Baez and Bryant were top 10. Russell was top 10 at b-r and in the next 10 at BA and mlb but of course he wasn't in the Cubs system yet. By the end of 2014, Baez was technically no longer a prospect while Russell and Bryant were both top 5. If the Cubs weren't intent on trying to screw him over, Bryant would have been up mid-2014. Anyway, once the BPJ trade went down, the Cubs probably did have 3 top 10s. (Soler never cracked the top 10 it seems ... in the 40s pre-2014, #12-22 pre-2015.)

Almora was also top 25 pre-2014 but that's as high as he'd get. Schwarber was drafted in 2014 and was ranked around #50 pre-2015 (BA put him #19 but BPro had him #77). Happ was around #50 pre-2017. Hendricks never made the top 100.

If there's a key bit there though it's that the Cubs didn't have a lot to do with it. Full credit for Baez who they (well, Hendry) drafted as a high-schooler. But Bryant was a highly developed college hitter who, in hindsight, was probably ML-ready on the day he was drafted and certainly by mid-2014. Russell was mainly an A's product. Schwarber was a more advanced hitter than expected and moved quickly (while not learning to catch although obviously the knee injury probably spoiled that plan anyway). Almora never developed enough. They deserve at least some credit for Hendricks but my impression is that was more a good job of development at the ML level. Happ is an interesting case, the Cubs probably did a good job there.

Soler was signed mid-2012, in the majors 2 years later after 650 minors PAs but they deserve at least some credit there. Torres was signed mid-2013, debuted in the US in 2014, was probably top 10 at the time of the 2016 trade. Eloy signed and debuted about the same time, broke out in 2016 at A ball and was around #10 at the time of the trade.

So they were very good at talent recognition and acquisition. But mostly they drafted guys who didn't need a lot of development or traded away guys very early. But at least they didn't screw up any of those top guys. As one of our Gonfaloners (sorry, can't remember which one) regularly points out, the Theo Cubs were absolutely dreadful at getting anything out of later picks or lower-level signings.

Jed's been doing it a bit different. In trades, he's mainly getting back the very young A ball guys (Hopefully a Gleyber and Eloy in there somewhere). His drafts are too soon to judge but looks like he's got a thing for overdrafting on the first pick so he's got money to buy out some HS kid's college commitment with the 2nd pick (looks like he's done it the last two years). I don't know if it makes sense to turn a #7 and a #47 pick into the equivalent of two picks around #20-25 but I can imagine that might work out. This plan is probably still (at least) two years away from producing a bevy of top 100 prospects.

I feel very suspicious of the Hoyer FO - I feel like Hoyer's a guy who wants to maximize "value" more than he wants to maximize wins. Would he take a risk on the Jon Lester deal like the Cubs did in 2015, or would he be worried about how the last 2-3 years would turn out? All the talk from him since he took over the top job has seemed more like a guy who is too cautious to waste money on a deal like that - so much talk about "spending smart" and "maximizing investment" or whatever, and not a lot of talk about doing what it takes to win.

We'll see. Right now this is not an organization that has a ton of talent in it, and virtually none of what they do have is close to contributing to a legit contender. And he's already failed pretty hard in the sense that he said a couple years ago that this was going to be a quick turnaround and not a long rebuild like we saw a decade ago.

And I don't get the sense that there is much of a "plan". For example, they remade their offense because it was too reliant on the HR and too prone to strikeouts, and wanted an offense geared more towards contact. Only that didn't work out like they planned. So now it's, "gosh, we really need to address our lack of power" and Franmil Reyes of all people is a guy they want to give a long hard look to with an eye to the future. They seem like they're just kinda flopping around. And sure, it's a rebuild, but what exactly is "the plan" here?