It wasn't meant to be this way. From the moment he became part of Roma's youth system Alberto Aquilani was identified as one of the brightest prospects to emerge in years and yet now, just over a decade later, he moves to Fiorentina looking to rediscover that early promise.
Having finally ended a Liverpool career that was always ill-fitting and never truly began in earnest, the 28-year-old moves to a club now synonymous with rebuilding the reputation of fallen stars. He will be hoping the famous Viola shirt can do the same for him.
Much has changed since the fresh-faced 17-year-old made his debut for his home-town club, then led by Fabio Capello. Never idolised the way fellow Roman's Francesco Totti and Daniele De Rossi are by the Giallorossi faithful, he was often viewed as lazy and was berated by the Italian media for 'not wetting his shirt' following Italy's Euro 2008 exit. It was against this backdrop he made the high profile £20 million switch to Liverpool in the summer of 2009, a necessary sacrifice for the Sensi family in order to keep the capital club afloat amidst mounting debts.
Aquilani's respect for Roma, combined with a need to play in the Champions League to test himself in the toughest of environments eventually led him to Liverpool, a club which, from the outside at least, were in a position to offer him everything he could have wanted. Stepping into a role vacated by the departure of Xabi Alonso to Real Madrid seemed, to many observers, ideally suited to both Aquilani's technical characteristics and the needs of the team.
Huge expectation was placed upon his shoulders by an Anfield crowd looking for a replacement for their beloved Alonso, who had been made to feel unwanted by then manager Rafael Benitez. Aquilani arrived injured, unable to debut until November 9 and, by the end of the campaign, had made just eighteen appearances with the Spanish coach questioning his mentality and commitment to the club.
He did however manage to put together a run of games toward the end of the season during which he looked increasingly comfortable, despite the criticism directed against him for being too lightweight. Statistics do show however that the widespread belief that he struggled to suit the sheer physicality of the Premier League were somewhat misjudged, with Opta showing his assist rate was one every 136 minutes played, the best of any player among Europe's top five leagues.
But he would never dominate games in an instantly recognisable manner like Steven Gerrard and, after spending such a large portion of their transfer budget on him, Liverpool fans were bound to become ultra-critical of their newest addition. The whole team struggled and the club endured its worst start to a season since 1987: knocked out of the Champions League at the group stage then failing to qualify for the elite competition for the first time in seven years.
Changes were inevitable and, sensing an opportunity to benefit from this strained relationship, Juventus offered the player a route back to Italy. Aquilani would become the player many always believed he would, controlling games and becoming a vital component of Gigi Delneri's side. His passing was superb and he developed the defensive side of his game incredibly, showing an application and determination that had been previously unseen.
Yet come the end of the campaign, the midfielder found himself cast out of a club seeking a new identity. Delneri left - replaced by Antonio Conte - and before his loan had officially ended so too did Aquilani. Andrea Pirlo arrived on a free transfer and became the man Conte shaped his side around. That move created space at Milan and Liverpool sent him out on loan to the San Siro, this time with a far more reasonable transfer fee agreed should the Rossoneri decide to make the move permanent.
It never materialised however, Massimiliano Allegri instead somehow preferring hard-working journeymen like Sulley Muntari and Antonio Nocerino to the craft, guile and creativity of Aquilani. Milan also failed to agree a deal with Liverpool and he once again returned to pre-season with the fourth manager of his brief flirtation with the red half of Merseyside.
Having now chosen to reunite with his former Roma team-mate Vincenzo Montella - new coach of Fiorentina - Aquilani could be forgiven for wondering how he would have fared under the tutelage of incoming Liverpool boss Brendan Rodgers. Having watched his Swansea team exhibit real flair, especially in the way they valued possession, the midfielder might have been an ideal match for the new coach's style of play, particularly having spent the summer with the incredibly similar Cesare Prandelli.
Yet he'll never know; instead he treads a path that Federico Balzaretti and Mattai Cassani among others have already travelled and moves to Florence to resurrect his ailing career. That he did enough at Juventus - the only place he has been a first-team regular since leaving Roma - to play his way back into national team contention will give him the belief he is still good enough to become the player he always promised to be all those years ago.
That it is Montella who now leads the Viola also must be considered an important factor as the young coach will know just how much potential remains unfulfilled with Aquilani. He too demands that his side plays an adventurous and modern style which can only benefit a player searching for somewhere, someone, to believe in him for an extended period. Once believed to be more talented than Roma legend Daniele De Rossi, Aquilani may never realise his true potential but, in Fiorentina, he may have found a club willing to at least let him try.