Liverpool's 5 most dramatic transfer collapses including two failed medicals

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Liverpool
Liverpool's 5 most dramatic transfer collapses including two failed medicals

When Liverpool come calling, players rarely say no.

Yet it's not always that simple, as Moises Caicedo will tell you. On Friday, Liverpool agreed a club-record £111million deal with Brighton to sign the Ecuador international. At that stage, everyone thought he was heading to Merseyside... everyone but the player himself.

Caicedo rejected Liverpool's advances and by Sunday night, Chelsea agreed a £115m deal for his services. The Reds and the Blues may have drawn 1-1 at Stamford Bridge on Sunday afternoon, but it was the latter club who won this transfer battle. Caicedo is still to be officially unveiled as a Chelsea player, although this is just a matter of time.

It's not the first time Liverpool have failed to get their man. Here, Mirror Football take a look at five other dramatic transfer collapses involving the Anfield club.

Nabil Fekir

Five years ago, Fekir was widely expected to join Liverpool. The Reds agreed a transfer fee with the France international's club, Lyon, and personal terms. Yet the move collapsed at the last minute when a knee issue appeared on his medical... or so it was claimed.

Chelsea complete record-breaking Enzo Fernandez transfer after deadline day rush eiqruidrtidezinvChelsea complete record-breaking Enzo Fernandez transfer after deadline day rush

Fekir was left bemused. After all, this was a man who helped his country win the World Cup that same summer and had just enjoyed a 23-goal season with his club. He later insisted that his knee was fine and the transfer collapsed because of his agent.

Liverpool's 5 most dramatic transfer collapses including two failed medicalsNabil Fekir joined Real Betis after his Liverpool move collapsed (Getty Images)

What do you make of Moises Caicedo's decision to snub Liverpool for Chelsea? Let us know in the comments below!

"It was a dark moment," Fekir told The Times when asked about his failed transfer in 2021. "I saw plenty of things which weren’t true. It was said the knee stopped me going to Liverpool but that wasn’t true... the knee was fine.

"I had a problem with my agent, my adviser. It was the agent responsible for the deal not going through. Of course I was disappointed not to go to Liverpool, very disappointed because Liverpool are a great club."

Fekir, now 30, joined Real Betis a year later and has since scored 28 goals in 138 games for the Spanish club. He's not played for France in three years.

Loic Remy

Liverpool's 5 most dramatic transfer collapses including two failed medicalsLoic Remy moved to Chelsea after Liverpool backed out of a deal (Getty Images)

Liverpool thought they had bagged a bargain after agreeing an £8.5m fee with QPR for Remy in the summer of 2014. The France international spent the previous season on loan at Newcastle, where he scored 14 goals in 26 Premier League games.

Yet Liverpool pulled out of the deal late on after Remy failed his medical. The player revealed in 2014: "I came for the medical tests and everything was fine and after that they wanted to be sure everything was fine with my heart.

"They asked for a specialist for the heart and apparently the guy said they did not 100 per cent agree if I could keep going or had to stop football. I didn't understand because they knew (about the issue) before I came."

Remy added: "I was more confused by Liverpool saying that I had medical problem because it is not fair. I have seen the best specialist in London and he has told me I can still play so it was not good from them. 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."

Yet it all worked out in the end for Remy, as Chelsea came calling later that summer. Although he was never a guaranteed starter at Stamford Bridge, the striker won the Premier League title and the League Cup under the great Jose Mourinho. Now 36, Remy is still playing professional football after a recent spell with French side Brest.

Hakim Ziyech brutally denied deadline day transfer as PSG furious at ChelseaHakim Ziyech brutally denied deadline day transfer as PSG furious at Chelsea

Lee Bowyer

Liverpool's 5 most dramatic transfer collapses including two failed medicalsLee Bowyer could've been a Liverpool player two decades ago (Getty Images)

Bowyer was one of the Premier League's most notable English midfielders back in the summer of 2002. Liverpool's manager Gerard Houllier was a big fan of the Leeds star - admiring his ability to score from midfield - and wanted to bring him to Merseyside.

Leeds were struggling financially and accepted a £9m bid from the Reds, with Bowyer in the final year of his contract. The player even completed a medical, but the two parties failed to agree personal terms. In the end, he joined West Ham six months later.

Liverpool claimed they decided against the transfer for a "variety of reasons". A statement added: "Gerard Houllier was not convinced the player had either the hunger or desire to play for the club, qualities which are essential for any Liverpool player."

Bowyer replied: "I never asked to go on the transfer list and made it clear to Mr Ridsdale (Peter, Leeds chairman) that I had reservations when they accepted Liverpool's bid. So it is probably in the best interest of all parties that the deal did not go through."

Yevhen Konoplyanka

Liverpool's 5 most dramatic transfer collapses including two failed medicalsYevhen Konoplyanka was close to joining Liverpool in 2014 (Getty Images)

Konoplyanka almost became a Liverpool player nine years ago after they triggered his release clause. Yet Dnipro president Ihor Kolomoyskyi refused to sign the paperwork and the move collapsed, leaving the Ukraine international in tears.

"I was crying," Konoplyanka recalled in an interview with Weszlo in 2022. "A delegation of serious people from Liverpool came to Dnipropetrovsk. We ate dinner. They were (willing) to pay as much as Ihor Kolomoyskyi wanted... I begged (to go)."

Liverpool's manager Brendan Rodgers said: "The club did everything possible to get the player in. We had our chief scout, managing director and doctor out there to conclude the deal - and from our point categorically Ian Ayre did a brilliant job trying to negotiate."

Konoplyanka went on to join Sevilla a year later and was part of the team that defeated Liverpool 3-1 in the 2016 Europa League final. Now 33, the winger is on the books at Romanian side Cluj. As for Dnipro, they went bankrupt in 2018.

Max Kruse

Liverpool's 5 most dramatic transfer collapses including two failed medicalsLiverpool changed their mind on Max Kruse in 2019 (Getty Images)

Liverpool were considering signing Kruse on a free transfer in the summer of 2019. The striker, who was out of contract at Werder Bremen, was 31 at the time and would've been a decent reserve for Roberto Firmino after a successful career in Germany.

Yet Liverpool changed their mind after Divock Origi's heroics in the Champions League. The Belgian scored a brace in the semi-final against Barcelona and found the net in the final against Tottenham to help the Reds lift their sixth European Cup in June 2019.

Liverpool kept hold of Origi and Kruse joined Fenerbahce instead. Now 35, Kruse is still playing professional football and recently signed for German second tier side Paderborn.

Kruse recalled last year: "We had been on the phone with Jurgen Klopp since February (2019). It was like I was transferred to Liverpool, only the signature was missing. It would be the pinnacle of my career. However, things developed very differently."

Kruse added: "The duo of (Daniel) Sturridge and Origi was going to be sold, I was going to sign. That was their plan. Then Origi started scoring many goals in the last part of the season. The club changed its mind after these goals."

Tom Blow

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