You make some good points. Some I agree with, others I don’t.
You talk of managerial instability in recent years having an impact on your young players however I’d argue that’s the model your club has been built on since Roman.
You’ve arguably not had managerial stability for 20 years now and the only manager that genuinely gave opportunity to your younger players during this period was Frank Lampard and he was quickly sacked. If anything this kind of environment is exactly why a player like Endrick would do well to stay away from the club, granted, this may change under Potter.
I see Chelsea having made numerous errors in terms of their young players and it’s surely no coincidence the vast majority of these talents decided they wanted to leave the club and couldn’t be persuaded to stay. Even now I see you making the same strange decisions with the loaning out of Colwill whilst spending over £100m on new centre backs in the same window (and trying to additionally sign Gvardiol!).
In terms of getting young players in and around the first team you seem quite good but at that point it all goes wrong.
Yeah I definitely didn't mean it like the managerial instability is a recent thing. Like you said that was the model of the club and for a long time no Chelsea manager even bothered with the youth to begin with because the managers themselves weren't afforded any time when hard times came around. In the first ~15 years into Roman's regime I would consider that to have been a somewhat justified approach because it's what brought us plenty of trophies and marks by far the most successful time period in the club's history, and ranks quite highly even across all clubs in England after the turn of the century.
That said, the standards have dropped a lot in the last 4-5 years and even under Roman the managers weren't really expected to win titles anymore and top 4 has been considered enough for a good while now. Coincidence or not but in the same time we've slowly but surely started seeing more and more youth products given a chance, with a bunch of them even becoming very much regulars in the first team. Some have still fallen through the cracks who perhaps should have been given a role in the team, but we've still had a very healthy amount of club-raised youngsters in the team lately. What I meant by the 'recent years' bit was only really regarding the players we were discussing.
But yeah, there has definitely been a shift in policy even in the last years under Roman and now under the Boehly-Clearlake leadership the talk is they are planning to build a team for long term success focused mostly on the younger players, be they from the club's own academy or imports from elsewhere. I wouldn't expect every player to be 21 or younger when joining the club and there will definitely still be the occasional experienced player signed in or about their prime years but the overall feel of the future squad building seems to be quite different compared to the Roman era.
It's true this summer we signed a couple of veterans in Sterling, Koulibaly and Aubameyang who don't really fit into the ideology of building a young squad but that was very likely down to Tuchel being heavily involved in the transfers. While Tuchel is in my opinion a world class coach he is not a squad builder for long-term projects, nor is he all that good with young players. A good comparison for Tuchel would be Conte or prime-Mourinho who can get the best out of a squad while spending money on signings for the here and now but not really so much for the future. Now we have Potter who seems to be more in line with what the owners are reportedly planning so it's going to be interesting to see what happens. I just hope he's fully backed by the new owners in that he gets given the time required to see what he can do with the squad and also what he, together with the recruitment team that's been built behind the scenes, can do in the transfer market.
How that long term vision actually comes into fruition is still a little bit up in the air but I still don't think it's very sensible to look at what happened or didn't happen with young players in the first ~15 years into Roman's regime and use it as a baseline today for someone like Endrick to make their decision about whether to join the club or not. So much has changed from those days that basically the only thing that's still the same is the name of the club. I still think we won't actually land Endrick but even if he doesn't join I think the signings we do get will be similar to him in that they're young with high potential to improve.
In terms of Pulisic it seems he was very much another big money panic buy as his monster fee was never really justified and based on pure speculation that he might improve. Instead he’s gone stale.
If anything, Pulisic was a panic buy in the sense that the transfer was finalized for the coming summer already in the January of 2019 when the club execs very likely already knew we would be getting a transfer ban that would prevent us from properly replacing Eden Hazard who had already been promised a transfer in the previous summer of 2018. At the time we also had Willian and Pedro on their last legs with both of their contracts ending in 2020 so Pulisic was brought in as a long term replacement for all three, despite overlapping with Willian and Pedro in the team for one season.
When the signing of Pulisic was made I looked at his numbers and didn't think he was anything special. I suppose for a 20yo lad he was doing alright but most of the transfer fee was based on potential, like it is with all young players, and the club probably saw some marketing potential to tap into the USA market due to him being American. If he had developed into a better player with us the commercial value would have been huge but as it is, all we have got to show for him being American is a lot of yanks arguing on social media that he should be starting despite the player not being good enough for it.