A look at Liverpool's top five failed transfers is truly embarrassing

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Liverpool have currently got their tail tucked firmly between their legs.

At the beginning of the week it looked as if the Reds had Mohamed Salah and Virgil Van Dijk in the bag for close to £100 million.

That's certainly not the case now.

The red half of Merseyside had to send an apology to Southampton for their pursuit of Van Dijk and have now ended their interest in one of the hottest centre-backs on the market.

Worse still, it's not the first time the club have failed so spectacularly in the transfer market. Below are five of Liverpool's worst transfer muck-ups.

Clint Dempsey

This embarrassing saga ended with another apology from Liverpool. In 2012 the Reds wanted to bring the American to Anfield in a deal worth £3 million, but Fulham held out for £5 million.

The Reds' co-owner Tom Werner made a personal visit to then Fulham owner Mohamed Al-Fayed and even sent an open letter giving a detailed apology for the manner of their pursuit. Oh dear.

Swansea City v Fulham - Premier League

Loic Remy

Damn Liverpool's medical team! The Reds looked like they were going to secure Loic Remy from QPR in 2014, but during his medical the club discovered a heart problem that turned them off.

However, Chelsea decided there was no risk and he ended up with a Premier League winners medal in his first season. Of Liverpool's decision, Remy said: "Even if they don't want to sign me, okay, but they don't have to put that in the newspapers because, then, all the other clubs after are afraid."



Liverpool were the European champions in the summer of 2005 and attempted to bring in Simao from Benfica to strengthen their side for a push towards the league title.

He was on a plane to complete the move when Benfica pulled the plug mid-flight. Liverpool were left powerless as the Portuguese winger turned right back around and went home.

(FILES) This file picture dated 25 Novem...

Gareth Barry

It seemed as though Rafa Benitez was obsessed with bringing Gareth Barry to Anfield at one point, even shopping Xabi Alonso to other clubs to free up the funds to do so. Sounds literally mental now, doesn't it?

In the end, Liverpool signed Albert Riera instead and Barry has since gone on to win the league with Man City. Now, ironically, he plays for Everton.

Liverpool v Aston Villa - Premier League

Lee Bowyer

Put the picture of Lee Bowyer the occasional football thug out of your mind for a second and remember the free-scoring midfielder for Leeds.

Liverpool agreed a £9 million fee for Bowyer back in 2002 and, at the time, he was one of the most productive midfielders in the league. However, Liverpool refused to succumb to his wage demands with Bowyer later stating: "I never asked to go on the transfer list and made it clear to Mr Ridsdale that I had reservations when they accepted Liverpool's bid."

In other words, he didn't want to move so plucked a ridiculous number out of the air!

Lee Bowyer of Leeds United pleads with referee

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