Last summer, Liverpool were a club receptive to evolution and owner John Henry should have picked the Portuguese manager to lead that journey, not play it safe with the popular appointment of Kenny Dalglish.
Andre Villas-Boas was the perfect fit for Liverpool rather than Chelsea
Andre Villas-Boas has had to endure the indignity of fans chanting the name of his former mentor during the past few matches.
He is cutting an increasingly forlorn figure on the touchline, his crouching pose now looks more desperate than dynamic.
The spectre of Jose Mourinho will always loom large over the career of Villas-Boas, so to choose to manage Chelsea, where his former boss gave himself the label of the "Special One", was only going to serve to magnify the comparisons.
Yet there could have been an alternative stage for him to cut his 33-year-old teeth in the Premier League. In the north west of England there was a club prime for revitalisation and an opportunity for the young Portuguese manager to escape the shadow of his compatriot and forge a career in England.
Liverpool would have been a better fit and a more judicious choice for Villas-Boas. The move looked to be on the cards when reports from Italy said Villas-Boas had turned down a move to Roma because he had signed a pre-contract deal with the Anfield club.
It made perfect sense and the protracted nature of the subsequent full-time appointment of Kenny Dalglish suggests Fenway Sports Group were torn between the identity of their preferred candidate. John Henry, the owner, suggested as much in a subsequent interview in October 2011: "Initially our blueprint was for a younger manager".
He could have easily been talking about Villas-Boas. His appointment would have fallen in line with the philosophy of the Boston Red Sox, Henry's other sports team.
In 2002 Henry hired the 28-year-old Theo Epstein, making him the youngest general manager in the history of the Major League. Two years later he helped deliver the World Series to the city for the first time in 86 years. He added a second three years later.
Yet Dalglish, at the age of 60, was offered the Liverpool job full time and Villas-Boas was parachuted in at the deep end at Chelsea. Why did Villas-Boas not end up at Liverpool? Well, Liverpool probably did not want to match the £13 million (Dh74.75m) a year salary he was offered at Chelsea and probably because Henry wanted a popular appointment to help usher in his new era at Anfield.
Henry acknowledged he knew "virtually nothing about Liverpool Football Club nor EPL [English Premier League]" when he took ownership. So what better way to smooth the transition of the takeover of Liverpool than by employing the man etched so intrinsically into it's fabric.
Dalglish was a safe option, an appointment that would have received a ringing endorsement on the Kop. Villas-Boas would have been a risk.
You can hardly blame Dalglish for pushing his credentials and accepting the job to manage one of the most famous clubs in the world again, but he should really have put Liverpool's best intentions ahead of his own.
Instead he should have guided Henry in an ambassadorial role, sat alongside his former strike partner Ian Rush in the directors' box and led the search for a young, long-term manager he could have educated in the rich traditions of Liverpool.
With the endorsement of Dalglish, Villas-Boas would have been confident of launching his reign with the approval of the loyal fans who hang on Dalglish's every word.
The Portuguese would have inherited a team receptive to evolution, unlike the Chelsea squad where the players that need to be phased out are resistant and wield too much power.
He would have been reunited with Steve Clarke, the incumbent Liverpool first-team coach, who he worked with at Chelsea under Mourinho as part of the back-room staff when the club won two Premier League titles, an FA Cup and two League Cups.
He would have had a greater say over transfers than he does at Chelsea - the lack of game time for Gary Cahill and Romelu Lukaku suggest they were not signings sanctioned by Villas-Boas - and, you suspect, put the vast amounts of money used to sign Stewart Downing and Jordan Henderson to much greater use.
Disciples of Dalgish will, quite rightly, point to the fact that the Scot has navigated Liverpool to the quarter-final of the FA Cup and is on the brink of landing their first trophy in six years on Sunday.
Yet he also presided over the appalling handling of the Luis Suarez affair and shown little tactical acumen over how to convert nine home draws into wins. Every team has an off day but the anaemic performance in the 3-1 defeat at the Championship-bound Bolton Wanderers raised question marks over Dalglish's ability to motivate the players.
Villas-Boas has not made too many waves at Chelsea and appears to be battling against the tide, but they are two places above Liverpool in the table and look like being England's sole hope in the Champions League this season.
He is not afraid to evolve the squad - something needed at Liverpool as Jamie Carragher, in particular, and Steven Gerrard reach the autumn of their careers - and implement a new style of play. It is difficult sometimes to decipher how Dalglish is instructing Liverpool to play.
The hiring of Villas-Boas at Anfield in the summer of 2011 would have been the Boston Way. And, done right, it could also have been the Liverpool Way.