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Ranked! Liverpool's 10 worst signings of the Premier League era

Features
By Greg Lea published 13 April 2018

When you purchase through links on our site, we may earn an affiliate commission. Here’s how it works.

Worst Liverpool signings

Worst Liverpool signings

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.

Yet it hasn’t always been that way for the Reds, with their recent revival set against the backdrop of questionable deals from their 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 title…

Page 1 of 11
Page 1 of 11
10. Torben Piechnik

10. Torben Piechnik

Signed from: Copenhagen (£500,000), 1992

Although Graeme Souness’ 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.

Istvan Kozma and Nigel Clough are blots on the former captain’s copybook, but Piechnik, who arrived from Copenhagen in 1992 with a glowing reputation after his performances for Denmark at that summer’s European Championship, was the worst of the lot.

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.

Page 2 of 11
Page 2 of 11
9. Bruno Cheyrou

9. Bruno Cheyrou

Signed from: Lille (£3.7m), 2002

Gerard Houllier explained how Cheyrou “has his [Zinedine Zidane's] ability to pick a pass, and moves a little like him,” while suggesting that at five years Zizou's junior, the Frenchman could follow Robert Pires and Sylvain Wiltord in becoming 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 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).

Page 3 of 11
Page 3 of 11
8. Charlie Adam

8. Charlie Adam

Signed from: Blackpool (£6.75m), 2011

Charlie Adam's heroics in Blackpool’s promotion fairy tale of 2010 were followed up by an impressive maiden campaign in England's top flight – so much so that in the January 2011 transfer window, Liverpool made a £4.5m bid that Tangerines gaffer Ian Holloway, in his usual calm fashion, described as "disgraceful".

Adam stayed for the season but when Blackpool went down, Kenny Dalglish got his man. Although Adam possessed a strong passing range, fine set-piece delivery and the helpful knack of scoring from distance, he was better as a big fish in a smaller pond – and shortly after Brendan Rodgers' Anfield arrival, the Scot joined Stoke for £4m. He had made just 37 appearances.

Page 4 of 11
Page 4 of 11
7. Andy Carroll

7. Andy Carroll

Signed from: Newcastle (£35m), 2011

Carroll arrived at Anfield with genuine potential, even if he was unlikely to ever match the standards set by predecessor Fernando Torres – sold to Chelsea the same day for £50m. He was also a significant gamble as the club’s record signing, but at 22 and having scored 11 goals in 19 Premier League games for Newcastle, there was hope that the Geordie could become the Kop’s new hero.

However, Kenny Dalglish’s blueprint for success – shifting the ball out wide and crossing in for the big man up top – was by now somewhat dated. Carroll bagged 11 in 58 games, notably the winner in the 2012 FA Cup Semi-Final against Everton, but that summer Brendan Rodgers quickly shifted him on. West Ham bought him for £15m: a club record for them, a £20m loss for Liverpool.

Page 5 of 11
Page 5 of 11
6. Stewart Downing

6. Stewart Downing

Signed from: Aston Villa (£18.5m), 2011

Few supporters backed Liverpool’s pursuit of Downing from Aston Villa, and this only heightened the demands on Kenny Dalglish’s new winger who had been earmarked to provide for Andy Carroll in attack.

Yet Downing was a woefully uninspired signing, unable to inject flair into Liverpool’s attack and shrinking while Craig Bellamy and Maxi Rodriguez shone. He survived at the club longer than many expected, but the writing was on the wall when Brendan Rodgers began fielding him at left-back. He joined West Ham in August 2013 for around £5m.

Page 6 of 11
Page 6 of 11
5. Christian Benteke

5. Christian Benteke

Signed from: Aston Villa (£32.5m), 2015

Liverpool have made some major mistakes in the transfer market, and their failure to plan adequately for Luis 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. The issue was that Liverpool didn’t need a big bloke up top, but rather 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 compensate for his lack of movement.

Page 7 of 11
Page 7 of 11
4. Alberto Aquilani

4. Alberto Aquilani

Signed from: Roma (£17.1m), 2009

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.

Page 8 of 11
Page 8 of 11
3. El Hadji Diouf

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, with Gerard Houllier buying him instead of Nicolas Anelka, who had been on loan at Anfield. Diouf was unsuccessful (five goals in 78 appearances) and unloved: Jamie Carragher said “his attitude disgusted me,” Steven Gerrard claiming that he “had no real interest in football” and “cared nothing about Liverpool”. He joined Bolton permanently in summer 2005 and, obviously, scored in his first game against his old team.

Page 9 of 11
Page 9 of 11
2. Sean Dundee

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 Gerard Houllier and Roy Evans, but was clearly not fit to lace the boots of Anfield’s ‘God’. A South African who had been scoring in the Bundesliga, Dundee played just five times for the Reds; he failed 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.

“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.”

Page 10 of 11
Page 10 of 11
1. Paul Konchesky

1. Paul Konchesky

Signed from: Fulham (£3.5m), 2010

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, he was woefully out his depth at Anfield. Konchesky outlasted Hodgson, but not for long; he was loaned 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.

Page 11 of 11
Page 11 of 11
TOPICS
Premier League Andy Carroll Charlie Adam Stewart Downing Paul Konchesky Christian Benteke El Hadji Diouf Alberto Aquilani Gérard Houllier Graeme Souness Brendan Rodgers Kenny Dalglish Roy Hodgson
Greg Lea
Greg Lea
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Greg Lea is a freelance football journalist who's filled in wherever FourFourTwo needs him since 2014. He became a Crystal Palace fan after watching a 1-0 loss to Port Vale in 1998, and once got on the scoresheet in a primary school game against Wilfried Zaha's Whitehorse Manor (an own goal in an 8-0 defeat).

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