Call it the Chelsea paradox. On Monday their under-18s will run out at Manchester City’s purpose-built Academy Stadium for the first leg of the FA Youth Cup final. It will be Chelsea’s sixth final in eight years – three of which ended in triumph – and comes just days after their under-19s lifted the Uefa Youth League with a 3-2 victory over Shakhtar Donetsk in Nyon, Switzerland

And yet. Until one of those young players becomes the first to establish himself as a first-team regular since John Terry did so 15 long years ago, the accusation will always be that Chelsea’s commitment to developing their own players is only so much hot air.

The two sides last met in the FA Youth Cup final in 2008 and looking back at that Chelsea XI is a sobering experience. Only Patrick van Aanholt, now at Sunderland, has gone on to have a career in the top flight. The other names that leap out do so mostly for the wrong reasons. There is Gaël Kakuta, the much-heralded Frenchman who nearly cost Chelsea a Fifa transfer ban but whose career stalled via a series of loan moves that led most recently to Rayo Vallecano.

In midfield, Michael Woods was emblematic of an earlier era when Frank Arnesen splashed the cash to raid rival academies and controversially picked off Woods and Tom Taiwo from Leeds United, a move that eventually cost Chelsea £5m. Woods now plies his trade at Hartlepool near the bottom of League Two.

Chelsea and City have poured fortunes into their academies at a time when the Premier League has been trumpeting its £340m investment into its elite player performance plan, a scheme that sought to comprehensively overhaul player development.

The scattergun Arnesen era is long past and Chelsea now insist the recruitment of young talent is far more targeted and tightly focused on English youngsters and the very best older teenagers from abroad, such as Nathan, the Brazilian 19-year-old they are set to sign from Atlético Paranaense for £4.5m.

The argument runs that a confluence of factors has given this crop of youngsters the best chance yet to succeed where players such as Josh McEachran and Ryan Bertrand, who won a Champions League medal but had to leave for Southampton for first-team football, failed.

That glass half-full view takes in the fact that the club hierarchy are now supposedly signed up for the long haul and place player development somewhere near the top of their priority list.

After a decade of £1bn-plus invested by Roman Abramovich to bring dazzling silverware and success (as well as its share of fear, loathing and paranoia), the chairman, Bruce Buck, and the top executive team led by Marina Granovskaia and Eugene Tenenbaum are now committed to a different course. In a world of financial fair play it is one that involves breaking even, growing their own and casts the second coming of José Mourinho, who pitched up two years ago in his short-lived “happy one” guise promising to build as well as buy, as a man committed to bringing through the kids. That is the vision but it does not yet match the reality.

“If you don’t bring kids through the academy, the best thing is to close the academy,” he said in December of a state-of-the-art facility that costs Chelsea something in the region of £8m a year to run. “If the kids are not good enough or the work not good enough and you don’t bring kids up, then close the door and use the money to buy players.”

Mourinho has said that if one or more of Izzy Brown, Dom Solanke and Lewis Baker do not become stars he will have failed. “They will be Chelsea players. And when they become Chelsea players, they will become England players, almost for sure,” he said at the start of the season.

More recently, the midfielder Ruben Loftus-Cheek has been talked up as the man most likely to. While the strategy in recent years has been to send youngsters out on endless loan spells in the hope of getting them the competitive experience that all agree promising players between 18 and 21 are desperately lacking, Mourinho has already said the rangy Loftus-Cheek will be an exception. “Loftus-Cheek is to stay and I think to stay and to play … you don’t have this kind of talent every couple of years,” he said.

At Chelsea’s Cobham training complex they call it “crossing the road” – the moment when academy prospects are invited over to train with the first team.On the wall of that academy is the mission statement: “A world class learning and development environment programme that fosters a culture of excellence, pride and unity – that nurtures young players so that they achieve maximum potential.”

And all the signs are that Mourinho does indeed take much more interest in development sides than he did in his first spell, holding regular meetings with his assistant, Steve Holland, the technical director, Michael Emenalo, and the academy director, Neil Bath, to track their progress.

Watch any of the development sides play and it is clear there is an attempt to imbue them all with the same approach. Yet while Mourinho is happy to talk the talk, there is little sign so far that he is prepared to walk the walk – generally limiting young players to cameos in the cup competitions.

Unless there comes a point at which they are thrust into meaningful action at the highest level, the danger must be that they will stay trapped in the no-man’s land of endless loan spells or hovering somewhere between the first team squad and the under-21 league.

Mourinho recently admitted that Chelsea was “not the best habitat” for young players to break into the side, such was the pressure of chasing titles. There is some frustration at the external clamour for immediate results among those responsible for developing Chelsea’s youngest and brightest – even if that is itself something of an irony at a club not known for its patience.

Yet there is some truth in it. Nat Chalobah, sometimes talked of as though a busted flush, is only 20 and impressing in his latest loan spell at Reading. Even McEachran, who became the poster boy for squandered Chelsea talent and is currently one of several young players parked at Vitesse Arnhem, is just 22.

Both are also examples of Chelsea’s strategy of farming players out on loan, especially between January and May. The teenage Brazilian full back Nathan looks likely to be the next to come in and immediately disappear.

During Chelsea’s close-season tours Mourinho will seek to calibrate the progress of his army of loanees, which currently stands at 27, sifting through to see who might make his first-team squad and who should be sent back out on the road. Patrick Bamford, now a hero at Middlesbrough, is just one whose summer fate could be telling.

The club insists every player is signed with a view to making the first team, with Eddie Newton given the task of keeping close tabs on every loanee. But looking at the mind-boggling comings and goings – and the big profits made on the likes of Romelu Lukaku (sold to Everton for £28m) and Kevin De Bruyne (£18m to Wolfsburg) – it is impossible not to conclude Chelsea are effectively operating a shadow squad that in an FFP era is acting more as a money-making exercise than a pipeline to the first team. In their ideal world, of course, it would be both.

The Chelsea experience touches on all the questions the Football Association and the Premier League are grappling with – most tellingly how to ensure young players, and in particular English ones, establish themselves in the first team between 18 and 21.

In a rare recent interview with the FA website, Bath insisted the “holy grail” remained bringing players into the first team and suggested he knew it was time to deliver. “I do believe that we have young players that can be future Chelsea players. I’m strongly passionate about that because I think we’ve got the best players we’ve ever had,” he said.

“If it doesn’t happen now over the next few years then it will be an interesting period – because the whole footballing fraternity will need to look at this.”