Chelsea's class of 2012 fail to make grade

Chelsea manager Andre Villas-Boas watches the defeat at the hands of Napoli (AP)

As he left the San Paolo Stadium on Tuesday, walking out alone to the team bus, Villas-Boas could be forgiven for reflecting that the faith he had expressed in the Chelsea squad he inherited last summer had been more than a little overstated.

The Chelsea manager arrived last summer promising a lightness of touch when it came to the old guard who had carried the club through the most successful period Stamford Bridge has ever known. He talked of "exploiting talent" and "freeing decision making", of improving the contribution of the big guns like Frank Lampard, John Terry and Didier Drogba. He appeared every inch the diplomat.

Even at the time it seemed optimistic that the core of the successful Chelsea team built by Jose Mourinho (above), by then edging into their thirties, could somehow be reconditioned to fight another day. Certainly, it did not take long for Villas-Boas to decide that the old certainties in the Chelsea team were no longer worth hanging on to; that, in fact, those old certainties should be disposed of immediately.

Villas-Boas has clearly fallen out with some of Chelsea's big names over the last few months but Tuesday's team selection was not especially radical. If Terry had been fit he would have started against Napoli and had Ashley Cole not missed the two preceding games he too would have been in the team. In terms of omissions based on "technical considerations" it came down to Lampard and Michael Essien. The nature of the subsequent 3-1 defeat, however, meant that the focus was on Villas-Boas's team selection.

It has long been a personal view that Villas-Boas is right to tackle the big issue at the heart of Chelsea: the transition to the next generation beyond the Mourinho team. He might have done so indelicately at times, he may have bruised some egos along the way but at least he has attempted it. The problem is that the Chelsea team in waiting is not good enough.

Compare the current Chelsea team to the one that won the club's first Premier League title in 2005 and went on to – with some changes – the club's only Champions League final appearance three years later. Money has been spent (see panel, right), but the quality of the team has not improved, or even been sustained. Rather it has dipped dramatically.

In 2006 Mourinho had wrapped up his second Premier League title. Cole, Michael Ballack and Andrei Shevchenko were about to join that summer, albeit with the loss of William Gallas to Arsenal.

In the 2005-2006 season, Mourinho could call upon a back four of Paulo Ferreira, Ricardo Carvalho, Terry and Gallas. In midfield he had Claude Makelele in front of the back four which permitted Lampard and Essien to go forward. On the wings were Arjen Robben and Damien Duff. In attack was Drogba, then 25.

It did not stop there. On the bench Mourinho had Hernan Crespo (in 2005-06) and Eidur Gudjohnsen as back-up strikers. He had the option of Joe Cole, arguably in his prime, to change games. Looking back now that would have been a difficult team for any club to replace but, sadly for Chelsea, they seem to have made an expensive hash of it.

Change had to happen at Chelsea but Tuesday's performance, vulnerable at the back, haphazard in attack, was a world away from Chelsea at their best. It is why Villas-Boas's predecessors hesitated to change Mourinho's winning formula. Left with no alternative, Chelsea's manager forged ahead with the change but it has done his reputation, and his nascent career, few favours.