Liverpool’s current hierarchy are known to drive a hard bargain when it comes to signing new players – and supporters are sometimes left disappointed when transfers fall through.
Their overall strategy has worked out pretty well, though, with the Reds winning the Champions League in 2019 and a first English top-flight title in three decades in 2020.
And it is not only under FSG’s ownership that Liverpool have missed out on high-profile names and been forced to settle for next-best options.
We’ve looked back at 10 deals the Reds came incredibly close to sealing in the Premier League era to see what happened next.
Teddy Sheringham
Former Liverpool boss Roy Evans wanted to sign a 29-year-old Sheringham from Tottenham in 1995 to add experience to a young squad featuring the likes of Robbie Fowler, Steve McManaman and Jamie Redknapp.
“I had a chance to bring Teddy in, but the club policy on transfers was no players over 28,” Evans told The Anfield Wrap in 2011. “He went to play until he was 38, or was it 48!
“But we needed that experience. We had John Barnes, a bit of Rushie, but we needed a little bit more with those younger players.
“Teddy was a great player and knew when to party and when to play and he could have told those kids ‘This is the right time, this is the wrong time’ – that sort of help for Barnesy and Rushie might have gone down well.”
Sheringham, who actually went on to play until the age of 42, instead joined Manchester United, winning the Treble in 1999 and PFA Player of the Year in 2001. Liverpool turned their attentions to Stan Collymore, who had been and gone by 1997.
READ: Roy Evans talks Liverpool frustration, attacking football and battling Man Utd
Lee Bowyer
Perhaps not a fashionable name, but Bowyer had been the catalyst in Leeds United’s midfield during their run to the Champions League semi-finals in 2001.
The one-cap England international’s time at Elland Road, however, had been mired in controversy as he had to stand trial having been accused of GBH.
But Liverpool were willing to give Bowyer a chance to revive his career, only to be turned off by the player’s indifference during contract negotiations in the summer of 2002.
“I couldn’t believe Lee Bowyer had not jumped at the chance to play for Liverpool FC,” Phil Thompson wrote in his autobiography.
“Better players than him would have walked all the way to Anfield. We had made a big commitment on our side, but it had been all one way.”
Bowyer went on to eventually join West Ham in January 2003, where he was relegated, while the Reds plumped for Salif Diao, who failed to recreate his heroics at the 2002 World Cup.
READ: A forensic analysis of Salif Diao’s wonderful goal at the 2002 World Cup
Simao
Liverpool started the summer of 2005 as champions of Europe, but it was clear the squad needed upgrading.
Rafa Benitez identified Simao, who had just scored 22 goals to fire Benfica to the title, as the man for the troublesome left-wing berth.
“Now the operation is very advanced and we wait for a final solution in the next few hours,” the player’s agent, Jorge Baidek, told Sky Sports amid reports his client was flying to Merseyside for a medical.
But Benfica tried to up the transfer fee as the deal reached a conclusion and Liverpool pulled the plug.
Simao went on to score at Anfield as Benfica knocked Liverpool out of the Champions League. Harry Kewell started both legs of the defeat on the left wing.
I sometimes feel out of touch with European football when I keep thinking things like “I wonder if Liverpool will be in for Simao this time?”#bbcdeadlineday
— Tom Worsley (@tew1984) January 31, 2018
Dani Alves
Liverpool were linked with Alves, then of Sevilla, in the summer of 2006, and the Brazil legend has since revealed he “pretty much had an agreement” with the Reds to make the move.
“For whatever reason it didn’t happen at the last moment and I really don’t know why,” he told FourFourTwo in 2017. “I had other people representing me back then.”
Alves, who won his first cap for Brazil that year, went on to join Barcelona in 2008, which didn’t work out too badly for either party.
Liverpool, meanwhile, signed Alvaro Arbeloa and Jermaine Pennant for their right-hand side. That went less well.
Loic Remy
A move for Remy appeared set to go through, only for the plug to be pulled after a medical had taken place.
Liverpool were concerned at a heart issue that had previously been detected at Marseille in 2010, despite the striker being cleared to play football four years prior to the Reds’ interest.
Remy instead left QPR for Chelsea, while Liverpool ‘replaced’ Luis Suarez with the combined signings of Rickie Lambert, Divock Origi and Mario Balotelli. None were anywhere near Suarez’s level, but to be fair, Origi has become a true cult hero.
Alexis Sanchez
In the same summer as the Remy transfer saga, Liverpool made Sanchez their primary target to replace Suarez.
Despite the Reds reportedly offering more money for the forward, the player preferred a move to London and instead joined Arsenal.
“To not get him was obviously bitterly disappointing,” Brendan Rodgers rued. “He’s a world-class player with outstanding quality and even bigger work rate. He would have been perfect for us.”
Rodgers even went on to admit that Lambert and Balotelli were not suitable signings for the style of pressing football he wanted to play.
Gareth Barry
Our former editor Rob harbours a bit of a weird man-love for Barry, but even he admits it’s a bit mental to look back at Benitez wanting to replace Xabi Alonso with the then-Aston Villa man.
Liverpool supporters sang “you can stick your Gareth Barry up your arse” at a pre-season friendly and the club ultimately failed to clinch a deal for the England international.
The Reds went on to almost win the Premier League, thanks in no small part to the outstanding form of Alonso, but come the following summer the Spaniard departed for Real Madrid and Barry joined Manchester City.
READ: 17 of the best quotes on Xabi Alonso: “It was clear he was royalty’
Virgil van Dijk
Liverpool landed themselves in a spot of bother in the summer of 2017 in their pursuit of Van Dijk.
Southampton made a formal complaint to the Premier League accusing the Reds of making an illegal approach for the defender, who met with Jurgen Klopp without permission from the Saints.
“We apologise to the owner, board of directors and fans of Southampton for any misunderstanding regarding Virgil van Dijk,” a Liverpool statement read. “We respect Southampton’s position and can confirm we have ended any interest in the player.”
Klopp was instead forced to stick with Dejan Lovren, Joel Matip and Ragnar Klavan in central defence – at least until January, when Liverpool finally landed their man by making Van Dijk the most expensive defender in history.
It’s gone alright, hasn’t it?
Nabil Fekir
Like the Remy deal, Fekir’s proposed £53million move broke down after his medical revealed a knee issue. Or at least that’s what we initially thought.
The collapse of the deal caused a split with his then-agent, Jean-Pierre Bernes, who later said that the move in fact broke down after Fekir’s brother-in-law stepped in at the last minute.
Bernes claimed that he had negotiated a full agreement between Liverpool and Lyon, and Fekir had posed with the shirt and been interviewed for LFC TV. But the aforementioned brother-in-law then arrived to demand a commission, saying that the negotiations needed to start over.
”When the Liverpool guys witnessed this cinema, they immediately [backed out],” Bernes told Canal+, “sometimes when a player has an injury, representatives can make an effort to make it work.”
Fekir later came out to say that the reports were false, stating: “Lots of lies were told and they affected me. Especially those told about my family. It hurt them and me. Especially when you know that’s what being told is false.”
That summer, Liverpool signed Xherdan Shaqiri as their attacking midfield option. He didn’t set the world alight at Anfield. Then again, neither has Fekir at Real Betis. Perhaps things worked out for the best.
Timo Werner
Klopp was intent on signing his compatriot Werner, so much so that he personally got on the blower to tell the former RB Leipzig man to get himself to Merseyside.
Yet after the pandemic struck the Reds’ top brass decided they couldn’t fork out £50million and Werner went to Chelsea.
Given he’s often looked like he couldn’t shoot a fish in a barrel, Liverpool fans might be thankful he did.
Diogo Jota came in from Wolves instead and, despite struggling with injury problems, managed to outscore Werner in 2020-21.
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