Trent top of Liverpool-dominated list of most valuable free transfer exits
With Trent Alexander-Arnold confirming his exit from Liverpool this summer, we looked at the most valuable of all free transfers.
There’s no Sol Campbell on here because it happened in the before-times, but here’s a list of every club’s biggest free transfer regret if that’s more your bag.
10) Youri Tielemans (Leicester City to Aston Villa)
“From the first day I set foot on this ground, your warmth and passion embraced me. Victory and triumph, love, hope and even defeat,” wrote the Belgian midfielder as he confirmed what we had all long knew: He would leave a relegated Leicester City with an FA Cup winner’s medal and the knowledge that he could have done little more to stop the slide from two consecutive top-five finishes to relegation.
In truth, his final year at Leicester was poor after a failed transfer to Arsenal left him ‘mentally gone’. We expected Arsenal to return when he became available on a free transfer in 2023 – it really did feel like a no-brainer – but it was Aston Villa who won that particular race. “The manager was selling me this idea of playing Champions League and I really bought into it,” said Tielemans, who would be playing in Europe’s elite competition a year later.
After a tricky first season in Villa colours, he has since thrived in the Champions League and Premier League, where he has made a good case for making the Premier League XI of the season.
READ: Alexander-Arnold joins list of every Premier League club’s biggest free transfer exit
9) Ander Herrera (Manchester United to PSG)
The Spanish midfielder was reduced to tears on a Manchester United podcast when discussing his exit from the club: “I got the Player of the Year award by the fans and the club didn’t call me that summer to sign a new contract, and they did with other players. That was painful for me, honestly.”
Herrera won the individual gong on the back of United’s most successful post-Sir Alex Ferguson season, in which he played a key role in their League Cup and Europa League titles, and memorably man-marked Eden Hazard out of a clash with Chelsea in perhaps the defining game of his United career.
But the new contract did not arrive that summer and a lame offer as his deal came to a close was comfortably improved by PSG. “There is red in my heart,” said Herrera as he confirmed his departure.
He ranks pretty high in a (largely awful) list of Manchester United transfers post-Fergie.
8) Kevin de Bruyne (Manchester City to…)
“I don’t know about the future unfortunately. I have shown I can still play here, otherwise I don’t do what I do these last four or five weeks,” said Kevin De Bruyne after striking the only goal as Manchester City beat Wolves, taking him to 250 goal involvements under Pep Guardiola.
He has won six Premier Leagues, one Champions League and seven domestic cups (an eighth could come in the FA Cup this month) for City, making him one of the most decorated players in Premier League history.
The Belgian is clearly very upset not to be offered terms by City, meaning his 10-year reign as one of the best midfielders in Premier League history is coming to an end. Or is it? His form in the final weeks of his City stay has prompted some cheeky links with Liverpool, while Aston Villa are said to be very interested.
“Let’s talk about the statue – for me he is Manchester City’s greatest ever player,” said Jamie Carragher. Would the club still build him a statue if he stays in the Premier League? They would probably quite like him to slink over to the semi-retirement of MLS.
7) Gini Wijnaldum (Liverpool to PSG)
“What this person – this wonderful, joyful, selfless person – has done for our team and club I cannot sum up in words, in truth, because my English is not good enough,” said Jurgen Klopp as Wijnaldum played his 237th and final game for Liverpool.
The Dutchman had barely stopped running in five years at Anfield which earned him Premier League and Champions League medals, but he fell victim of FSG’s reluctance to hand long contracts to players in their 30s. He wanted to stay and Klopp wanted to keep him – he was ‘perfect’ for Klopp’s system – but a business decision was made.
It seemed that Barcelona would sign Wijnaldum – they are masters of the free transfer swoop – but PSG stepped in to offer twice the money. There he won a French league title but being wonderful, joyful and selfless buttered no parsnips in Paris and he is now in Saudi Arabia playing as a striker.
6) Emre Can (Liverpool to Juventus)
It’s been seven years since we said the free transfer exit of Emre Can from Liverpool should be met with ‘shrugs’, and we were absolutely right. As galling as it always is to allow a player worth £30m-plus to leave for nothing, he was never integral to a Liverpool side building towards Champions League and Premier League glory under Jurgen Klopp.
It helps of course that he was then pretty poor at Juventus (though his career has since been rescued by Borussia Dortmund) while Liverpool brought in Fabinho and immediately won the Champions League. Can was never missed.
5) Andreas Christensen (Chelsea to Barcelona)
“Having spent ten amazing years at this club, I felt now was the right time for a new beginning for me and my family,” said the Dane, not so fondly remembered by Chelsea fans after he made himself unavailable to play in the FA Cup final against Liverpool in 2022. The decision to leave had clearly affected the form of a player who had won the Champions League the year before.
There was enmity between club and player at the end, with Christensen blamed for twice reportedly reneging on verbal agreements to sign a new contract. He then engaged new agents who wanted to start the whole process again from scratch.
He won the title with Barcelona in his very first season but has been perpetually linked with a return to the Premier League, with the Spanish club likely to accept slightly less than his £430m buy-out clause.
4) Antonio Rudiger (Chelsea to Real Madrid)
In the same summer that Christensen left, Rudiger also departed Chelsea. And the Blues have been struggling for leadership at the back ever since; they have won nothing since the German left in 2021.
Rudiger admitted that the uncertainty surrounding Chelsea’s ownership and the knock-on effect on player negotiations were a big factor in his exit, saying: “For me, there was a gap between August and January, and that made me think “what’s going on”.
“You get pressure from other teams because it’s January and people don’t know what’s happening and you would have to wait until June because you have a contender to take over the club but even today you cannot talk to him because you have to go through Government stuff and everything.
“I didn’t want to wait until June to sort out my future because it’s been almost a year of uncertainty.”
And nobody can begrudge anybody joining Real Madrid, right?
3) Aaron Ramsey (Arsenal to Juventus)
“It all happened…I agreed to a contract they proposed,” said Ramsey when attempting to explain why he had left Arsenal after 11 years at the club. He claims that the offer was then retracted as manager Unai Emery decided he wanted to take the club in a different direction.
A few months later Emery was sacked by Arsenal and Ramsey has signed a deal with Juventus that gave him the highest basic salary of any British footballer. But there were few regrets from Arsenal as he never started more than 13 Serie A games in a season for the Italian giants (though he did win a Serie A title) before a loan spell at Rangers and a permanent exit to Nice and then Cardiff.
2) Paul Pogba (Manchester United to Juventus)
Only Manchester United could twice spend money on a mercurial talent and twice watch him walk away for nothing.
‘For a boy that joined the academy at 16 to make over 200 United appearances and lift the Youth Cup, along with two major pieces of silverware, is something that should be applauded and celebrated,’ said Manchester United in a statement that somehow missed out the details of Pogba being allowed to walk away for nothing, re-join for £89m and then leave for nothing again six years later.
Relations between Pogba and the club had long since broken down but the second that Jose Mourinho referred to Pogba as a “virus” should have been the second they began plans to sell him and recoup some of their costs.
He later said that he wanted to leave in the summer of 2019 after his best season for Manchester United because he saw the writing on the wall about the direction of travel but the club denied him an exit; they would live to regret their reticence.
1) Trent Alexander-Arnold (Liverpool to, we presume, Real Madrid)
Only perhaps Kylian Mbappe and Lionel Messi have been more valuable free transfers. He has chosen adventure over comfort after winning everything at Liverpool.
