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, 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 Jose 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. The key figures in the Chelsea squad which won that second consecutive title have either grown old without suitable like-for-like alternatives being found or have left and not been replaced.
In the 2005-2006 season, Mourinho could call upon a back four of Paulo Ferreira, Ricardo Carvalho, Terry and Gallas. Wayne Bridge was an alternative left-back. In midfield he had Claude Makélelé in front of the back four which permitted Lampard and Essien to go forward. On the wings were Arjen Robben and Damien Duff and 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 given his subsequent performance in the World Cup finals that summer, 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.
Raul Meireles is no Makélelé. Ramires has great qualities but is nothing like Lampard in his prime. Florent Malouda is not the equal of Essien at his very best. Nor, it should be said, is Essien six years on and one cruciate knee injury down the road. And then there is Fernando Torres. You know that things have got really dire at Chelsea when they suffer a bad defeat and the fact that the £50m man spent the whole game on the bench is barely mentioned.
That is not to say there have not been successes. Juan Mata could one day be the kind of playmaker that David Silva has become for Manchester City, although it is doubtful he will ever be quite Silva's level. Daniel Sturridge is inexcusably selfish at times but his acquisition, questioned at first, has been justified. Branislav Ivanovic is generally solid, although he must take some responsibility for Edinson Cavani's goal on Tuesday.
Rebuilding title-winning teams is a notoriously difficult task and Chelsea, having achieved success in the Roman Abramovich era so quickly, have been less successful in moving on to the second phase. It is not like Abramovich has not tried – witness the investment in the new academy, the appointment of Frank Arnesen – it is just that it has not worked and now they find themselves with a lot of highly paid, ageing players who are simply not cutting it.
That is no consolation to Villas-Boas, who came into Chelsea last summer in the belief that he still had a squad that could challenge the very best in Europe. When he recognised that was not the case he decided that the club must take its medicine now and force the pace of change. As a result he has a disgruntled group of senior players and then the preferred new boys, like Meireles, Ramires and David Luiz, as well as Gary Cahill, who are finding the going hard.
Change had to happen at Chelsea but the ragged nature of Tuesday's performance, vulnerable at the back, haphazard in attack, was a world away from Chelsea at their best in Europe. It is why Villas-Boas's predecessors have hesitated to change Mourinho's winning formula of six years ago. Left with no alternative, Chelsea's manager has forged ahead with the change but it has done his reputation, and his nascent career, few favours.
More misses than hits: The Chelsea buys since 2006
Chelsea's big signings in the last six seasons. This season's buys, the likes of Meireles, Romeu and Lukaku, can't be judged fairly yet.
John Obi Mikel £16m from Lyn Oslo/Man Utd (2006) MISS
Andrei Shevchenko £30m from Milan (2006) MISS
Salomon Kalou £8m from Feyenoord (2006) MISS
Michael Ballack Free from Bayern Munich (2006) HIT
Ashley Cole £5m + Willam Gallas from Arsenal (2006) HIT
Khalid Boulahrouz £8m from Hamburg (2006) MISS
Florent Malouda £13.5m from Lyons (2007) HIT
Branislav Ivanovic £8m (2008) from Lokomotiv Moscow HIT
Nicolas Anelka £15m from Bolton (2008) HIT
Jose Bosingwa £16m from Porto (2008) MISS
Deco £8m from Barcelona (2008) MISS
Daniel Sturridge £4m from Man City (2009) HIT
Yuri Zhirkov £18m from CSKA Moscow (2009) MISS
Yossi Benayoun £5m from Liverpool (2010) MISS
Ramires £18m from Benfica (2010) HIT
Fernando Torres £50m from Liverpool (2011) MISS
David Luiz £26m from Benifica (2011) MISS
Juan Mata £23m from Valencia (2011) HIT
Total spend since 2006 league win £339.5m
Total received £134.4m
Net spend £205.1m
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