Bought for a huge sum of £17 million, Aquilani was brought in to replace the departed Xabi Alonso as Liverpool's playmaker.
Though he showed glimpses of brilliance, his first season was marred by injuries. He made just 26 appearances for the team, many of which were as a substitute.
At the end of the season, the manager who had brought him to the club, Rafael Benitez, was fired. This, coupled with Aquilani's problems in adjusting to life in Liverpool, meant that the Italian would be moving away before his five-year contract expired.
Since then, Aquilani has been sent out on loan by two different managers: Roy Hodgson and Kenny Dalglish.
Even the new Reds boss, Brenden Rodgers, who has openly talked about Joe Cole returning to the club, has shown no interest in bringing Aquilani back.
The question that arises: Why is Liverpool facing such a big issue in selling a player who is good enough to play for such big clubs?
The first loan spell at Juventus included a buyout option for the Turin club, reported to be at £13 million. Though he impressed during his spell there, Juventus decided to pass on the option to buy, as they felt the price was too high.
Aquilani returned to Liverpool, only to be sent out on loan again to AC Milan, with a buyout clause at a much lower £6.4 million. However, AC Milan did not get Aquilani to play for the 25 matches that would have made it mandatory for them to buy him and decided not to use the buyout clause.
Aquilani's future still remains unclear, and another move to Milan might not be ruled out, according to ESPN. The report talks about Rodger's knowledge that Aquilani has problems in adjusting to life at Liverpool, and how a move away from Anfield looks to be the more likely option.
Liverpool would obviously now be taking a huge hit on the £17 million they spent on him. And the eventual price that Liverpool may be getting might be much lower than £6.4 million that Milan needed to spend, considering that Aquilani now only has only two years remaining on his contract.
Liverpool currently would be looking to get about £4-5 million for the player, which is also an optimistic estimate.
Questions need to be answered by the people who handle the club's transfers.
Two years ago, Aquilani was a highly-rated midfielder with good credentials while playing for Roma, with four years left on his contract. Surely, two years ago, Aquilani would have been worth more than the £4-5 million that Liverpool would now be getting from any possible suitors.
Why has Liverpool not been able to sell a player who was good enough to play for Juventus and AC Milan? Surely, other clubs would have been interested in signing the player.
One argument could be the player's preference for the club he wants to move to. Though one should respect his preferences, that should not be having such a huge financial impact on the club.
If Liverpool had been decisive enough over the last two years, they would have made lost much less. And they would have spent a lot less effort each year in deciding the player's future.
Most Liverpool fans hope that this year, a decision is made on the the player's future, and that the chapter is closed on Aquilani, whether he stays in Liverpool or decides to move on.