The 34-year-old Portuguese tactician was recruited during the summer with a clear managerial remit: out with the old and in with the new - a revolution, as opposed to evolution - doing whatever it takes to rebuild.
However, just seven months into his Chelsea tenure, Villas-Boas is already under huge pressure to improve results in one of the world's least forgiving leagues, while their Champions League inclusion, both this season and next, is already shrouded in a cloud of doubt.
His surprise appointment off the back of an impressive quadruple in his debut managerial season with Porto, propelled him into the Premier League spotlight, leaving him with the unenviable task that even the most experienced of managers would struggle to comprehend.
The challenge of rebuilding while maintaining results and a winning mentality is a trick that few have ever managed to achieve, and one that even fewer have been given the required amount of time to see through, particularly at Chelsea.
Sir Alex Ferguson is the only contemporary boss to have accomplished such a feat. Even Arsene Wenger - a man of 15 years more Premier League experience than Villas-Boas - hasn't come close to pulling that off, as his north London project continues to stall, with Arsenal approaching a seventh season without a single trophy.
To make Villas-Boas' task even harder, over the past eight years, Chelsea have won endless amounts of trophies despite a succession of managerial changes, with no fewer than seven different coaches taking seat in the Stamford Bridge dugout since Roman Abramovich's arrival in west London back in 2003.
The fact that the club has won so much without any managerial continuity is largely thanks to the core of players who have been on the books throughout – the likes of Petr Cech, Ashley Cole, John Terry, Michael Essien, Frank Lampard and Didier Drogba.
The general consensus around the club and in the dressing room is that it doesn't matter who is in charge, the Chelsea players will do the business on the pitch - providing they are given the opportunity to do so. And therein lies the problem for Villas-Boas.
His reluctance to continue playing the old guard and enthusiasm to give new players the chance to shine could well end up being the latest Blues boss' undoing. The blind faith that Villas-Boas has shown in under-performing stars has never been so apparent than in the 3-1 defeat at Napoli in the Champions League on Wednesday.
Daniel Sturridge and Juan Mata - as they have done all season - provided a hint of reason for optimism, but the likes of Raul Meireles, Ramires, and Jose Bosingwa, brought in ahead of Essien, Lampard and Cole, are simply not good enough.
As for David Luiz one day taking the place of club captain Terry at the heart of Chelsea's backline, that is unlikely to happen until he has at least mastered the fundamental basics of defending.
When the team sheet was released in Naples on Wednesday evening, Graeme Souness, in the Sky Sports studio, described Villas-Boas' line-up as the shortest suicide note in football.
From the outside looking in, Chelsea's young pretender is considered arrogant and aloof, with his apparent failure to acknowledge the contribution of senior players at Stamford Bridge leaving huge question marks hanging over his, and ultimately the club's immediate future.
Villas-Boas might call it a 'project', but right now, a more accurate term is a shambles.