We were very good at selling star players and reinvesting the proceeds at one time - selling Carrick (I think £16m) allowed us to buy Berbatov (for £11m I think) who in turn was sold on for £30m.
We also sold Modric (£30m I think, big at the time) and Bale for big money after buying them cheaply - Bale ended up costing us about £8m (as we bought back his 'extras') and we received close to £100m. Only issue is we didn't spend the Bale money that well with Eriksen and Lamela the only long term successes.
All that changed with Poch who apparently didn't want to sell Eriksen even after Eriksen said he wanted out - at that time we might have got £80m, whereas when sold we got was it £19m ? And 20/20 hindsight says we should have sold Dele at his peak for £100m+ ! The only big money raised was to sell academy players (Townsend, Mason, Bentaleb, Pritchard, Veljkovic et al) for circa £100m to buy the likes of Sissoko
And its not selling to raise funds which meant that towards the end of Poch reign we'd had windows from 2016 - 19 where we spent relatively big eg Sanchez for £43m who has not lived up to expectation, or on what seemed very decent punts such as Janssen, who Poch didn't play much ....... before throwing our CL winnings into the disastrous buying of Ndombele and Lo Celso in 2019 ...... but we never raised any money from selling good players during his reign.
I don't like Chelsea, but they have rinsed a lot of money by selling players. Even more so by allowing Lampard to bring through their academy players and then selling them (Abraham, Tomoli etc). Most other big clubs do it - so why not us ?
Had we sold the likes of Eriksen at their peak (say 2018) and reinvested in a couple of players who could develop into stars (as we have now with Sarr) we would not have ended up at end of Poch's reign with an aging squad and few youngsters. Paratici had a huge job to do, and he's done well to get us a better squad (but a couple more windows required) but its due to STOPPiNG selling some stars to re-invest that we had a big problem.
Yes I'm not disputing any of this.
But there would have been fucking riots had we actually sold Eriksen, Dele, and Kane etc.....
And we WERE absolutely slated for selling Modric, for selling Bale, for selling Berba.
Whilst Chavs have made some great sales by offloading mainly over-the-hill players to Woolwich (Luiz, Willian (although he looks great at Fulham), Cech, Hazard to RM. And they got great money for Tomori, Abraham, Hudson-Odi, and Ake.
Then there is this lot that never gets mentioned:-
Cuadrado, Drinkwater, Berkley, Batshuayi, Bakayko, Reme, Kenedy, Falcao, Torres, Schurrle, Fillippe Luis, Lukaku, Eto (biggest wages in the world), Ba, Emerson, Zappacosta, van Ginkel, Morata, Kepa (getting better but yet to repay the World record fee), Higuain, Pulisic, Werner, Ziyech, Havertz, Galagher bought him back now will almost sell again).
And then those that were great or v good but they sold Salah, DeBryn, Ake, Christiansen, Lampetey, Guehi.
A lot is about narratives around certain Clubs, this gets attached and repeated and reinforced. But those that get credited for being great in the transfer market like chavs it rarely goes hand in hand in looking at those they are stuck with, can't sell or have lost hundreds of millions over, no other Club has written off a debt of £1.5b of failed trading.
Edwards at Liverpool was praised to high heavens, what is to be made of LFC's business now? (I know he's left but it his role is to ensure there is a healthy conveyer belt of players coming through the academy and there's a pipeline of transfer targets profiled for every position. Southampton was supposed to be a model all clubs should aim at. Like Spurs Everton and I think Leicester also went after "star" DoF and technical directors widely praised for the roles at their clubs only to fail.
It's really difficult to isolate a period of time without framing the context to those years that preceded or followed.
With us, however, there is no denying that we have incrementally improved our squad year on year for nearly the past 20yrs. I still feel the loss of behind-the-scenes talent at Tottenham came around the time we lost Mcdermott, just look at how many of his old coaches/staff are now at Fulham (that Parker took with him). I can't say we've improved on that, mainly because I lost visibility to what we are doing here (I had a small opportunity to know what we did back then as I knew a couple of people now no longer at the club).
But there's nothing definitive - for any one position or player that we could have sold there is an equally powerful argument for keeping them. There is also the argument that Wenger put forward years ago that the purchase and sale of a player's valuations is a red herring and irrelevant. I wouldn't wholeheartedly agree with him, especially as he suffered terribly trying to shift cloggers in his "English Core" that were all on massive salaries just sitting out their time in u21's.
Finally, I think the whole of the PL is going to get fucked, we are already, in the transfer markets as the clubs from leagues outside the PL know there are loads of bargains to be had if a PL club is willing to terminate a contract or buy a player from their academy only to flip them in a year or 2 back to the PL for +£60m or have a player they can sell to PL for at least x5 they will get of a club in another league. PL clubs are getting fleeced. This only makes player trading harder for PL clubs.