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#5 Joe Cole (2010)
After a glowing and largely successful spell at Chelsea, Joe Cole moved to Liverpool on a free transfer in what seemed to be the biggest steal of the summer. The Reds just suffered a major setback as they failed to qualify for the Champions League for the first time in seven years. Out went Rafa Benitez, in came Roy Hodgson and we saw a lot of poor transfer deals being made, as pointed out already on this list. However, Cole was expected to stand out at Anfield and be their creative force in a new era for the club.
The former West Ham and Chelsea man instantly made headlines from the get-go, but for the wrong reasons. He received a straight red card for a late challenge on Laurent Koscielny within 45 minutes of his league debut for Liverpool against Arsenal. Cole followed that up by missing a penalty in a Europa League qualifier. He did not settle in well after that and lacked the passion it took to put on the famous red shirt. The entire 2010-11 season was an extremely difficult one for the former England international before he left Liverpool on loan to Lille.
Cole returned the following season but left in January 2013 to re-join West Ham, a place where he felt at home. The main reason why Joe Cole's time at Anfield was labeled as heavily disappointing was that he possessed an exceptional level of talent. Cole was a key part of a very successful period in Chelsea's history but he could not transform any of those good abilities to his game at Anfield. This was a huge waste of a transfer, despite being free. When Cole had signed, Steven Gerrard made a bold prediction that he would win the Player of the Year award and even compared him to Leo Messi. He could not have been more wrong.
#4 Alberto Aquilani (2009)
In the summer of 2009, Liverpool dished out £17 million to sign Alberto Aquilani from AS Roma. He was said to be an attacking replacement for the Real Madrid-bound Xabi Alonso. The midfielder was heaped on with massive praise from the likes of Francesco Totti and John Arne Riise. However, he arrived at Anfield with an ankle injury which turned out to be much more serious than what the Reds were led to believe. He did not make his full debut until December.
He did show some talent during his limited appearances for Liverpool, including a perfectly placed shot against Atletico Madrid in the Europa League semi-final. Unfortunately, Aquilani lacked the physical game of English football and the Reds were desperate to cash in on the Italian. Loan spells at Juventus and AC Milan were both not good enough to warrant a permanent transfer, so Liverpool ended up biting the bullet and accepting a huge loss on their Italian investment as he was sold to Fiorentina.
Aquilani still remains a curious case for Reds fans. Circumstances may have been a bit too harsh on him. Would he have succeeded at Anfield if he hadn't been injured for so long? It's hard to really answer that question. The fact is that Liverpool did make a huge mistake by getting Aquilani as Alonso's replacement. It was a risk-filled move, a rare one during those troubled times as well and it did not pay off one single bit.
