Alberto Aquilani, the signing the signalled the beginning of a dark era for Liverpool. He arrived on Merseyside in the summer of 2009 as the replacement for Xabi Alonso who had recently left for Real Madrid.
Hopes were high for the Italian, who had a big reputation in his home country. It's safe to say the transfer didn't work out.
Aquilani didn't make his debut until December of that year due to injury, while he largely flattered to deceive during the remainder of the season. After Benitez was sacked at the end of the campaign, it would also all but spell the end of the player's time at the club.
In an excellent article on The Athletic, James Pearce outlines how the deal for Aquilani came about. It's clear that he was far from first choice, but financial constraints meant he there were few other options.
Liverpool were in trouble at the time, with owners Tom Hicks and George Gillett struggling to repay the loan they had taken to buy the club. That meant little funds were available for the club to build on their second-placed finish the previous season.
Benitez's first choice signing was David Silva, while Stefan Jovetic was also considered. He was told that neither were affordable. Finances were so tight that Liverpool couldn't even afford the free transfer of Matthew Upson.
Aquilani was only available at £17.5million because of his injury problems. A member of Benitez's backroom team told The Atheltic:
Glen Johnson came in (for £17.5 million), but that deal was only possible because Portsmouth still owed us money for Peter Crouch...
David Silva was very much of interest. Rafa was Valencia manager when he was in their academy and knew his father, who had worked at the training ground there.
He would have been perfect but he just wasn’t affordable. If we’d had the money to make it happen, we would have signed Silva 100 per cent.
There were very few players in our price bracket who fitted the bill. Aquilani had been heavily scouted. He was ripping it up in Serie A and Italy had really high hopes for him...
We also needed a centre-back that summer and had a deal for Matthew Upson lined up on a free. He was an England international and the other lads had vouched for him being a good character, but it didn’t happen because the club said his wages were too high.
We ended up buying Soto Kyrgiakos from AEK Athens for £1.5 million instead, because his wages were so much lower. That’s how bad the situation was at that time.
You can read the article in full here.
