Liverpool’s 10 biggest transfer sale mistakes

Analysis

FT Desk

Liverpool are one of the biggest names in European football, being among the most successful clubs in the history of the Champions League and the English top flight.

Over the years, Liverpool’s squads have been filled with star players, and while many of the transfer decisions have proven to be good ones, there have been some blunders in recruitment.

A significant period without success saw a number of key players being sold to rival clubs, or other players lost for not nearly enough money compared to their worth.

Here is a list of the 10 biggest transfer sale mistakes that Liverpool have made.

Kevin Keegan - €600,000 (Hamburg, 1977)

Kevin Keegan was one of the world’s best players in the 70s, shining for Liverpool under both Bill Shankly and Bob Paisley, two legendary figures in the club’s history.

After six years at the club, with three Premier League titles, a European Cup and two UEFA Cup crowns, Keegan was allowed to leave for Germany, joining Hamburg.

Keegan immediately took to German football and went on to win the Ballon d’Or in consecutive seasons after leaving Anfield.

He would add a Bundesliga crown to his list of honours before returning to England with Newcastle and Southampton, and while Liverpool continued their rampant success right through the 1980s, it might have been even more significant had they kept Keegan in their ranks.

Steve McManaman - Free Transfer (Real Madrid, 1999)

Not only did Steve McManaman walk out on Liverpool in the summer of 1999, but his hometown club got nothing in return for it in one of the worst player departures in the club’s history.

McManaman had become a fan favourite after graduating from the Liverpool academy, developing into a star for club and country as he went to Euro 96 and the 1998 World Cup while with the Reds.

But as the club began to struggle to win major titles, McManaman joined Real Madrid with just one FA Cup and one League Cup under his belt.

His move was immediately justified as he won the Champions League in his first season, scoring a brilliant goal in the final, before adding another European Cup and two La Liga titles with Los Blancos.

Xabi Alonso - €34.5m (Real Madrid, 2009)

Xabi Alonso was one of the best midfielders in the Premier League and the world, but Rafa Benitez bizarrely told the Spaniard that he could be sold in that same summer window.

With Aston Villa’s Gareth Barry lined up as a replacement, Benitez let Alonso leave for €34.5m, suffering a double blow with the departure of Alvaro Arbeloa in the same window.

Alonso managed all the same honours as Arbeloa did at both club and international level, minus one Champions League, before joining Bayern Munich and winning three league titles there.

That sale was the beginning of a sharp decline for Liverpool. They never signed Barry, Benitez was sacked a year later and Liverpool finished seventh, beginning a seven-year period where the Reds made the top four just once.

Javier Mascherano - €20m (Barcelona, 2010)

Alongside Steven Gerrard and Alonso, Javier Mascherano formed one of Europe’s best midfield trios, but he left Gerrard on his own in the summer of 2010.

After Liverpool’s dismal season following the Alonso sale, Mascherano promptly left for Barcelona, for whom he was outstanding for seven and a half seasons.

The Argentine lifted the Champions League title twice with the Blaugrana and collected five La Liga titles, while Liverpool were left in a mess without him.

His influence was never replaced and his sale remains one of the biggest mistakes the club ever made in the transfer market.

Luis Suarez - €81.7m (Barcelona, 2014)

Luis Suarez almost single-handedly gave Liverpool a first Premier League title in over 20 years, and they simply had to keep him in the summer of 2014.

Having worked incredibly hard to fend off interest from the likes of Arsenal in previous years, Brendan Rodgers was ultimately unable to keep hold of him, receiving €81.7m for the Uruguayan, a club record sale at the time.

As Daniel Sturridge succumbed to injury and Mario Balotelli and Rickie Lambert proved unsuitable replacements, Suarez’s absence was immediately felt.

While they did perhaps everything they could to hold onto him, letting Suarez go was one of Liverpool’s biggest mistakes at the time, and only the successful Jurgen Klopp era made Reds fan forget about what could have been had the Uruguay international not been sold.

Raheem Sterling - €63.7m (Manchester City, 2015)

In quite the same way the Suarez saga unfolded, Raheem Sterling’s future dominated headlines for just about the entire 2014/15 season.

Sterling suddenly found himself leading the line for Liverpool with a lack of other options, but the Englishman saw trophies and success elsewhere as the Reds slumped back outside the top four.

Rejecting multiple offers to extend his contract, Sterling secured a move to Manchester City in 2015, going for €63.7m, a record for an English player at the time.

This sale strengthened a direct rival and turned out to be a major mistake from Liverpool’s point of view, with Sterling going on to win four Premier League titles and a myriad of domestic cups with the Citizens before joining Chelsea in 2022.

Georginio Wijnaldum - Free Transfer (PSG, 2021)

The departure of Georginio Wijnaldum in 2021 hurt Liverpool significantly more than anyone could have anticipated.

The Dutchman was one of Jurgen Klopp’s most important players, instrumental in the side winning the Champions League and Premier League in 2019 and 2020, respectively.

But at 30 years of age, Wijnaldum and Liverpool disagreed on terms for a new deal, and the club failed to do enough to convince him to stay as he left for PSG on a free transfer.

Allowing a crucial player to leave for free was a big mistake from Liverpool, as Wijnaldum became the first star player of Klopp’s team to move on. While things didn't work out great at PSG, Liverpool missed him greatly.

Sadio Mane - €32, (Bayern Munich, 2022)

Liverpool sold Sadio Mane to Bayern Munich in 2022 after six glorious years in red for the Senegalese forward, who won every possible trophy he could have in his tenure.

Mane was instrumental in Liverpool's Champions League win of 2019 and Premier League triumph in 2020, as well as contributing heavily to other successes after joining from Southampton in 2016.

He was sold after expressing a desire to leave, and Liverpool struggled to adapt without him, with the winger's energy proving crucial in their intense pressing game.

Once again, while Mane struggled at Bayern Munich and lasted only a year there, Liverpool flopped in the season after his exit and failed to finish in the top four. It took them a whole year to adapt to his absence before they started to shine again in attack.

Trent Alexander-Arnold - €10m (Real Madrid, 2025)

History would repeat itself for Liverpool when another homegrown hero walked out for Real Madrid in much the same way Steve McManaman had done 24 years earlier.

Academy graduate Trent Alexander-Arnold became one of Liverpool's key players under Jurgen Klopp and eventually vice-captain to Virgil van Dijk. A unicorn player in the truest sense of the term, the England international was a playmaking right-back, the likes of which the world had not seen before.

Because of his position, it was perhaps underestimated just how crucial he was to Liverpool's attacking play. As the old cliche goes, you don't know what you have until it's gone. That was certainly the case with Trent.

Feeling that he had achieved everything there was to achieve with his boyhood club, Trent decided to run down his contract and to pursue a move to Real Madrid, making himself persona non grata in his hometown.

It ultimately was not quite a free transfer because Real Madrid paid €10m to have him available a month early for the Club World Cup in June 2025, but it was nevertheless a damaging loss for Liverpool, who struggled to replace Trent not only positionally but also in terms of chance creation and passing.

Luis Diaz - €70m (Bayern Munich, 2025)

Luis Diaz was not always the most popular player during his three and a half years at the club. Signed from Porto for €49m in January 2022, the Colombian winger initially failed to have a consistent impact.

By the time the 2024/25 season rolled around, Diaz increasingly came in for criticism for his lack of attacking output. However, everything changed when Arne Slot arrived, under whom he enjoyed a brilliant season, scoring 17 goals as the Reds marched to the Premier League title.

That campaign was seen as an outlier, so when Bayern Munich offered to sign the then-28-year-old for a whopping €70m in the summer of 2025, it seemed a no-brainer to cash in on him. What a mistake it was!

While Diaz played out of his skin in Germany, Liverpool's attack misfired, with the left-wing position a particular weakness. Slot's misplaced faith in Cody Gakpo left the Reds ruing their decision to sell the Colombian.

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FT Desk

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