Liverpool have famously had several transfers fall through at the death, with Marc Guehi being the latest, but who else was close to moving to Anfield?
The transfer window can create its fair share of excitement, drama and disappointments, with it now playing a predominant role in how football clubs are viewed and assessed.
For Liverpool, they have had a long list of success stories, but also cases where a player has looked hours away from a transfer only for the deal to be called off.
From conducting LFCTV interviews to being inside MRI machines, let’s take a look at players who almost made the move to Liverpool.
Nabil Fekir (2018)
One of the most famous ones of recent times as screenshots of his interview with the club’s in-house media, in Liverpool attire, leaked, only for the deal to fall through at the death.
• How close was the deal? A deal worth £52.8m was agreed with Lyon, and the club’s medical staff had travelled to Clairefontaine to oversee a medical while he was on international duty.
• Why did it break down? Club sources cited an issue with his knee as to why the transfer did not go ahead, but it was later suggested that interference over Fekir’s contract led Liverpool to pull out.
• What happened next? Fekir later joined Real Betis in 2019 and stayed until 2024, before moving to Emirati club Al Jazira Club. He did later speak about his disappointment at not getting to work with Jurgen Klopp.
Loic Remy (2014)
After losing Luis Suarez, Liverpool looked to the Frenchman to challenge Daniel Sturridge, having already signed Rickie Lambert, Adam Lallana, Emre Can and Lazar Markovic.
• How close was the deal? The forward had flown to Boston to undergo his medical during the club’s pre-season tour after his £8.5m release clause at QPR was triggered.
• Why did it break down? He failed his medical due to known heart problems, which affected previous potential moves in his career.
• What happened next? He went on to sign for Chelsea and later went to Crystal Palace on loan. He signed for a further six clubs and announced his retirement in 2023.
Diego Costa (2013)
It can be hard to believe that Liverpool came close to adding the forward to their ranks in the summer before Brendan Rodgers came close to clinching the league title.
The Reds would go on to have a fair share of battles with the Spain international!
• How close was the deal? Liverpool submitted a £21.85m offer to trigger Costa’s release clause.
• Why did it break down? He decided against a move to Anfield, instead signing a contract extension at Atletico Madrid.
• What happened next? He turned into a dominant forward and twice made moves to the Premier League, first with Chelsea and later Wolves.
After leaving Stamford Bridge in 2017, he did return to Atletico for another spell. He has yet to officially retire but has been a free agent since January 2025.
Marc Guehi (2025)
Liverpool saw an opportunity to bolster their centre-back ranks with an experienced international, but waiting until deadline day proved the deal’s undoing.
• How close was the deal? It was hours away from being rubber-stamped. Liverpool had agreed a £35m fee and Guehi was undertaking his medical in London.
• Why did it break down? Oliver Glasner reportedly threatened to resign, Palace could not find an adequate replacement and the Eagles’ co-owner and chairman was at a fitness class, and thus final communication was delayed until the end of deadline day.
• What happened next? Guehi remained at Selhurst Park but signed for Man City in January after they offered £20m ahead of his free agent status this summer.
Moises Caicedo (2023)
Liverpool’s search for a marquee No. 6 took them to Moises Caicedo, and the club made a statement with their bid. But they agreed a fee despite the player always preferring a move to Chelsea.
• How close was the deal? Liverpool had agreed a then British-record £111m deal with Brighton and had a medical booked for the player.
• Why did it break down? Chelsea returned with an improved £115m offer and the midfielder preferred a move to Stamford Bridge.
• What happened next? He joined Chelsea, where he remains, and while initially struggling, he has become one of the Premier League‘s best.
Clint Dempsey (2012)
Rodgers wanted the American and the famous swap deal included future Liverpool captain Jordan Henderson, but the No. 14 refused to entertain the move.
Liverpool’s owners, however, had even accidentally released a statement suggesting Clint Dempsey had been signed.
• How close was the deal? Liverpool had submitted two bids for the forward on deadline day, but both were rejected.
• Why did it break down? The club did not offer what Fulham were looking for, and the Cottagers went on to complain to the Premier League over Liverpool’s conduct during their pursuit.
• What happened next? He instead joined Tottenham and managed just 12 goals in 43 appearances.
He has since explained that the deal to Liverpool “was pretty close,” but Henderson simply “didn’t want to make that change.”
Lee Bowyer (2002)
It looked like a promising coup for Liverpool as they chased Leeds‘ Lee Bowyer, but while his talent was not in question, his attitude was, and it prompted the deal to collapse.
• How close was the deal? A £9m fee was agreed with Leeds, and a medical was undertaken at Melwood ahead of finalising the transfer.
• Why did it break down? Negotiations over personal terms dragged on and the club eventually pulled the plug, even releasing a statement on the official website questioning Bowyer’s attitude throughout negotiations.
The statement read:
“Liverpool Football Club have decided not to go ahead with the proposed transfer of Lee Bowyer for a variety of reasons. Manager Gerard Houllier was not convinced the player had either the hunger or desire to play for the club – qualities which are essential for a Liverpool player.”
• What happened next? Half a year later, Bowyer signed for West Ham on a short-term deal, then Newcastle, back to West Ham, Birmingham City and, finally, Ipswich Town.
He has since admitted not joining Liverpool was his “biggest regret in football.”
Max Kruse (2019)
According to the German striker, Liverpool had lined up a free transfer in the summer of 2019 as they were to oversee the exits of Sturridge and Divock Origi.
• How close was the deal? Kruse claimed that he had been in talks with Klopp since February 2019, with a free transfer lined up and “only the signature was missing.”
• Why did it break down? After Origi played a pivotal role at the end of 2018/19, the club “changed its mind” and Klopp informed the German they would now stick with Origi.
• What happened next? Kruse eventually joined Fenerbahce, only for a dispute over unpaid wages seeing him leave his contract early and move to Union Berlin.
A return to Wolfsburg followed in 2022, but his deal was mutually terminated later in the year after a disagreement with manager Niko Kovac. A bullet dodged, perhaps!
Michael Laudrup (1983)
Michael Laudrup was one that got away for Liverpool as he became one of Europe’s greatest players during the 1980s.
Liverpool had sought to sign him as a 19-year-old, but they would be left to rue their late offer change.
• How close was the deal? A three-year contract had been agreed after he travelled to Liverpool with his father.
Laudrup later explained:
“We actually agreed a deal and I came over with my father to talk to Liverpool’s representatives. We agreed a three-year contract and went away thinking it was all done.
“But two weeks later they came back saying they wanted to offer me the same package, but for four years because I was still young and needed time to develop. I was disappointed because although nothing had been signed, we had an agreement.”
• Why did it break down? Liverpool wanted to offer the same financial package but over four years instead of three, and that change prompted Laudrup to reevaluate.
• What happened next? Liverpool would have had their head in their hands as Laudrup became widely regarded as one of the greatest attacking midfielders and playmakers of all time.
He starred for the likes of Juventus, Barcelona, Real Madrid, and Ajax.
Cristiano Ronaldo (2003)
Before he ever signed for Man United, Liverpool were in a position to sign the Portuguese forward when he was only 18.
• How close was the deal? A £4m deal was seemingly agreed when ex-assistant coach Phil Thompson dined with Ronaldo’s agent in Lisbon, who told them of his wage demands of £1m per year.
• Why did it break down? Man United swooped in after a pre-season friendly and they outbid Liverpool, who were none the wiser that they had been beaten to his signature.
• What happened next? Well, he went on to become one of the world’s best players with a successful career, namely at Man United and Real Madrid.
Dani Alves (2006)
Rafa Benitez had identified the 23-year-old right-back as an upgrade on Steve Finnan, but Liverpool refused to increase their offer to match what was being demanded.
It’s a recurrent theme!
• How close was the deal? Liverpool offered £7m, £1m short of Sevilla’s asking price.
• Why did it break down? They simply did not meet the asking price, keeping their purse strings tight despite spending £8m on Jermaine Pennant that same summer.
• What happened next? Alves would join Barcelona and become one of the most decorated footballers in history. It proved a huge misstep. What could have been, eh!
Gareth Barry (2008)
Another famous ‘what if’ transfer for Liverpool. Benitez wanted to sell Xabi Alonso and replace him with Aston Villa‘s Gareth Barry, which did not go down well.
• How close was the deal? Liverpool submitted a number of bids and Villa manager Villa manager Martin O’Neill had written to outline the terms that would be suitable.
• Why did it break down? Barry’s price tag was not met and Liverpool did not want to raise their offer despite going on to spend elsewhere that summer.
• What happened next? Barry initially stayed at Villa before moving to Man City and later Everton and West Brom, finishing his Premier League career with a record 653 appearances.
Liverpool would then lose Alonso to Real Madrid the following summer.
Gabriel Heinze (2007)
It would have been an incredibly rare occurrence if Heinze had moved to Anfield; in fact, he would have been the first to transfer directly between Liverpool and Man United since 1964.
A falling out with Sir Alex Ferguson prompted Heinze to look elsewhere for game time, and Liverpool were his club of choice.
• How close was the deal? His agent had written permission that Heinze could leave for the £6.8m offer Liverpool tabled.
• Why did it break down? Ferguson and United simply ruled that he would not move to Anfield, and that prompted Liverpool to take them to a tribunal.
The hearing found in United’s favour, consider us shocked!
• What happened next? The defender would make a move, but to Real Madrid and later Marseille. He would have proved a reliable option at Anfield. He now works at Arsenal as a first-team coach.
Luis Figo (2005)
Having lifted the Champions League trophy, Benitez wanted to strengthen his squad and the club lined up an ambitious move to sign Figo.
The 32-year-old was surplus to requirements at Real Madrid and would have been an eye-catching arrival just weeks after Steven Gerrard signed his new deal.
• How close was the deal? Reports claimed Liverpool had agreed a £50,000-a-week deal with Figo and were confident they would land him on a free transfer.
• Why did it break down? Real were looking for a £2m fee and Liverpool failed to show the initiative to get the deal over the line, stringing Figo along.
Figo once recounted:
“I would have liked to go. We talked a lot.
“One week they say, ‘No, wait, we can’t do it just now’ and then they sign a player. Then, ‘wait a few more days, we need to sort this first’, and they sign another.
“I think: ‘Bloody hell, are you messing with me, or what?’.
• What happened next? It was a big opportunity missed, even if Figo was closer to the end of his career than the start.
Figo instead moved to Inter Milan, where he won four consecutive Serie A titles before retiring in 2009.
Yevhen Konoplyanka (2014)
A name that was constantly mentioned across social media and still is to this day after Liverpool were made to jump through hoops to land Yevhen Konoplyanka.
• How close was the deal? A £20m fee and personal terms were agreed, and Liverpool chief executive Ian Ayre had flown out to Dnipro to seal the transfer, even having dinner with Konoplyanka.
• Why did it break down? The Ukrainian club’s owner pulled the plug at the last hour, refusing to sign the paperwork before the deadline.
• What happened next? His dream move was denied and the winger never truly settled anywhere after the failed transfer. Before retiring in 2023, he played in five different countries.