This is becoming a bit concerning

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How do we ever progress if we're constantly selling players in their prime? It doesn't make any sense.

It does make sense. We wont ever progress if we dont get into a position financially to act on our progress. As you said Ideally we sell them younger to maximize the value but a club in our position (like many others) simply cant afford to just sit by and watch players depreciate in value. Bring a player up, sell them for a big amount, buy two player who you can do the same with. That seems to be the best plan.
 


It does make sense. We wont ever progress if we dont get into a position financially to act on our progress.
Our "progress" is on the back of players in their prime. We don't make progress without them. Jags, Baines, Pienaar (albeit in a bad stretch of late is a key performer) Howard and so on. As much as we've been unhappy with them this season our defence last year was one of the best in the league and it was built around 2-3 players who you would have sold under a "cash in now when value is highest" policy.

Our two most valuable assets are Baines and Fellaini. We will finish lower in the league without Baines and Fellaini. That impacts our revenue significantly (even if we don't get relegated which is worst case and probably unlikely) and impacts the level of talent we can attract. It also impacts relationships with existing players ("they aren't supporting me with talent to fulfil my potential") and sends a bad message to players we are trying to attract ("we aren't trying to win now we are trying to win years from now.")

You are acting as if we have the same revenue and can attract the same players if we are tenth. I do not believe that is the case. You can't have it both ways and expect to attract great talent and make the same revenue while just being average. We get the best of the rest now (when we can afford it) because we are the best of the rest.

As you said Ideally we sell them younger to maximize the value but a club in our position (like many others) simply cant afford to just sit by and watch players depreciate in value.
That is precisely what we should do. Name another non-top club who holds onto their assets. There is none. Villa sold them all. They all sell. The non-CL teams usually are forced to sell players (or do so by their own free will to cash in). There are lots of clubs who have sold players over the last 10 years and it hasn't helped them at all. Why? A bird in the hand. You sell a player in the top 5 in his position and buy two or three new players with the money. You might actually be net behind on wages because of paying three v. one. Maybe one of them becomes top 5 but probably not all of them. Some are busts. Moyes is better than any other non-CL manager at signing players but he still spent 8m odd on Bily. We've seen it here after our big sales. You get some diamonds and you get some busts and in the end we're just fifth or sixth again which is where we started. It's what we've been doing pretty much. Why would that suddenly have a different impact? It is not a sustainable strategy and every single non-CL club in the league proves it because that is what they do and they never get anywhere. Recently we have retained key players and sold off players like Arteta (still good but wasn't playing as well for us) and Rodwell. I believe it's a big part of why we started so well this year (recent slide aside) that we haven't sold the likes of Baines, Fellaini and Jags (in some cases beaten back offers for them which makes me think this might actually be our plan).

Bring a player up, sell them for a big amount, buy two player who you can do the same with. That seems to be the best plan.
Based on what? Your best plan involves a manager who never makes a single bad buy. There is no such manager. If you sell one and buy two and one turns out as good as the one you sold then you've made a lateral move. Do you know how hard it is to identify a young cheap player who is going to be top five or ten in the league at his position? I would argue that is hard enough to do. So the thing that gets you back where you started is really, really hard. So how hard is the thing that gets you ahead? You need to sell a top-5/10 player and buy two of them younger and cheaper. It's near impossible which is why no other club (including ourselves) has ever done it on scale. What clubs have not tried (and I would argue we've perhaps come the closest ... and we've done the best of the chasing pack which I do not believe is a coincidence) is retaining talent in their prime.

If you can stuff more five star talent into your 11 available slots you will win more. Teams who sell in their prime players never have five star players so they never win that much.
 
I like the look of Chico from Swansea, seems like a great centre back. No idea how old he is etc but I think he could be a good addition.
 
Put Jags in goal, bring in Duffy, go 3 at the back, having a stand-in Goalie will concentrate their minds like nothing else....something needs to.

I like it, I like it a lot. Jags can hoof it as much as he likes, which is a lot.

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