From spitters to quitters, it's the Reds' worst transfers since the 1992/93 season - including two of their 10 most expensive acquisitions - as ranked by Jack Lusby of This Is Anfield
Liverpool are in their most fruitful period of transfer business for years, with the majority of Jurgen Klopp’s new arrivals delivering on the pitch and the club securing great value for their deadwood too.
Since Klopp arrived in October 2015, the German has been backed heavily by owners Fenway Sports Group. The big-money signings of Mohamed Salah, Sadio Mane, Virgil van Dijk, Alex Oxlade-Chamberlain, Georginio Wijnaldum and Naby Keita have been complemented by bargains in the form of Loris Karius, Ragnar Klavan, Joel Matip, Andy Robertson and Dominic Solanke.
Yet it hasn’t always been that way for the Reds, with this revival set against the backdrop of questionable deals from their recent past. In the Premier League era, the club have had as many misses as they have hits, no doubt setting them back in their quest for the top prize. This is the very worst of them...
10. Torben Piechnik
Signed from: Copenhagen (£500,000), 1992
Graeme Souness made a raft of errors during his ill-fated three-year stint as Liverpool manager, as he stripped the club back to its fundamentals in a bid to restore fortunes after Kenny Dalglish’s exit.
Although his show of faith in blooding a host of youngsters including Steve McManaman and Robbie Fowler was impressive, the Scot’s forays into the transfer market were decidedly less so. The likes of Istvan Kozma and Nigel Clough are blots on Souness’s copybook, but not worse than Piechnik, who arrived from Copenhagen in 1992 with a glowing reputation after his performances for Denmark at that summer’s European Championship.
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Unfortunately, Piechnik’s defensive ideals jarred horrifically with those of Souness. The Dane's unwillingness to adapt meant he made just 24 appearances for the club - a paltry return on Liverpool’s investment.
9. Bruno Cheyrou
Signed from: Lille (£3.7m), 2002
Few players in history are comparable to Zinedine Zidane, but Gerard Houllier was happy to make a bold claim about Liverpool’s new No.28 back in 2002.
The French manager explained how his 24-year-old compatriot “has his [Zidane's] ability to pick a pass, and moves a little like him,” while suggesting that at five years Zizou's junior, Cheyrou could follow Robert Pires and Sylvain Wiltord in adapting over time to become a Premier League star.
He went on to feature 48 times for the Reds, scoring five goals (only two of which came in 31 league appearances), and spent half of his Liverpool tenure on loan back in France.
Houllier’s misplaced faith in Cheyrou earns the latter a place on this list, as a representative of the otherwise-successful manager’s dismal attempts at cherry-picking hidden gems from his homeland (see also: Jean-Michel Ferri, Bernard Diomede, Gregory Vignal and Anthony Le Tallec).
8. Charlie Adam
Signed from: Blackpool (£6.75m), 2011
There have been few bigger one-season wonders in the history of the Premier League than Adam, whose heroics in Blackpool’s promotion fairy tale of 2010 were followed up by an impressive maiden campaign in England's top flight.
Adam was brought in to provide more quality in Dalglish’s midfield, as part of a depressing recruitment drive that features heavily in this top 10. However, it soon became apparent that the Scot was better as a big fish in a small pond at Bloomfield Road.
His natural abilities - a strong passing range, fine set-piece delivery and the canny knack of scoring from long range - were not enough to keep him afloat in a squad fighting to restore their place in the league’s upper echelons. It came as no surprise, therefore, that he joined the miscellaneous faces congregated at Stoke just one season after his big break.
7. Andy Carroll
Signedfrom: Newcastle (£35m), 2011
Carroll followed a similar trajectory to Adam, but the brutish Geordie at least arrived with the promise of genuine potential. He was a significant gamble as the club’s record signing, but at 22 and having scored 11 and assisted nine in 19 Premier League games for Newcastle, there was hope that he could become the Kop’s new hero.
However, Dalglish’s blueprint for success - shifting the ball out wide and crossing in for the big man up top - was undoubtedly dated. So while Carroll is more technically gifted than given credit for, his Merseyside move was doomed from the beginning.
Given the exploits of a man brought in on the same day, Luis Suarez, Carroll was able to shuffle out of the Anfield exit under less scrutiny. But Liverpool’s £20m loss when selling him to West Ham will have hurt.
6. Stewart Downing
Signed from: Aston Villa (£18.5m), 2011
Our third and final inclusion from Dalglish’s second reign in the Anfield dugout, Downing trumps both Adam and Carroll for his standing as the Kop’s pariah.
Few supporters backed Liverpool’s pursuit of Aston Villa’s Plain Jane, and this only heightened the demands on Dalglish’s new winger who had been earmarked to provide for Carroll in attack.
Downing was a woefully uninspired signing, unable to inject flair into Liverpool’s attack and shrinking while Craig Bellamy and Maxi Rodriguez - both of whom were signed for free - shone. He survived at the club longer than many expected, but the writing was on the wall when Brendan Rodgers began fielding him as a left-back. He was rightly carted off to West Ham in 2013.
5. Christian Benteke
Signed from: Aston Villa (£32.5), 2015
Liverpool have made some major mistakes in the transfer market, and their failure to plan adequately for Suarez’s move to Barcelona in 2014 is up there with the worst. Granted, Benteke was not brought in directly after the Uruguayan left for Catalonia - his immediate replacements were Mario Balotelli and Rickie Lambert - but his arrival was the most costly.
After the failure of Brendan Rodgers’ “calculated gamble” in signing Balotelli, Benteke was earmarked as the man who could transform the Reds’ attack. “I’ve not had another who could do that up front in the three years I’ve been here,” the Ulsterman said shortly after his debut.
The issue was that Liverpool didn’t need a targetman. They needed another fluid, adaptable forward who didn’t cost £32.5m and who wouldn’t skulk on the edge of the box berating his team-mates when they couldn’t turn water to wine with his lack of movement. In short, they needed Roberto Firmino - who was also signed that same summer but spent his first months under Rodgers playing as a wing-back.
Aquilani’s inclusion in this list, and his lofty placing as the Reds’ fourth-worst signing in the history of the Premier League, comes with more than a tinge of melancholy. The promising Italian midfielder arrived injured, was deemed the Real Madrid-bound Xabi Alonso’s heir and inherited the No. 4 shirt previously worn by former captain and Anfield favourite Sami Hyypia.
Aquilani made his debut in October 2009, almost three months after arriving. His first start came in December, his first of two goals in March and his last appearance for the club two days removed from his one-year anniversary as a Red.
Though his talent was undoubted, Aquilani just didn’t fit the billing on Merseyside and was sold to Fiorentina for just €790,000 in 2012. A baffling deal.
3. El Hadji Diouf
Signed from: Lens (£10m), 2002
There are few ex-Liverpool players more universally despised among supporters than Diouf: a tragic waste of potential more notorious for spitting at the opposition and taunting injured players than for anything he did with a football.
He joined the Reds following a breakthrough tournament with Senegal at the 2002 World Cup, but this quickly proved to be an anomaly in a disappointing spell on Merseyside. Both Jamie Carragher and Steven Gerrard are outspoken in their disdain for the striker, with the former explaining how “his attitude disgusted me,” and the latter that he “had no real interest in football” and “cared nothing about Liverpool”.
That two of the Reds’ most well-respected senior figures turned their backs on Diouf so quickly is a testament to the player’s character, and that this was backed up by just six goals in 80 games magnifies his failure.
2. Sean Dundee
Signed from: Karlsruher (£1.8m), 1998
One of the worst players to ever play for Liverpool. Dundee was brought in as cover for the injured Robbie Fowler during the co-managerial reign of Houllier and Roy Evans, but was clearly not fit the lace the boots of Anfield’s ‘God’.
Dundee played just five times for the Reds, failing to score in any of those appearances, with a battle for fitness and off-field issues compounded by a clear lack of faith in him from Evans himself.
“One player I do regret signing was Sean Dundee; he was terrible on and off the pitch,” Evans has since told LFCHistory.net. “He didn't take any notice of me, did what he wanted and lacked discipline. He certainly shouldn't have joined Liverpool.”
In terms of talent, performances and a synonymity with one of the most toxic periods in the club’s history, Konchesky is the worst signing Liverpool have made in the Premier League era.
Brought in as Roy Hodgson’s new first-choice left-back, having served under the Englishman at Fulham, he was woefully out his depth at Anfield. Konchesky outlasted Hodgson, but not for long; he was loaned out to Championship side Nottingham Forest just five months after making the move to Liverpool - three weeks after Hodgson was dismissed.
That a player of Konchesky’s calibre was playing at the club less than 10 years ago is both a damning indictment of their situation at the turn of the decade and a marker of the progress Liverpool have made since then.
Jack Lusby writes for This Is Anfield, the independent Liverpool website, and has been a regular FourFourTwo contributor since 2018. He is an expert on Liverpool's youth academy players and has a keen eye on ensuring transfer stories are sourced correctly, which means he is a proficient user of Google Translate.
