Premier League’s 20 Worst Transfers of All Time

What a waste of money! As Leeds are ordered to shell out £40m for a striker who played 48 minutes, CRAIG HOPE looks at the 10 worst transfers in Premier League history… including a current Liverpool player and two Sunderland flops

With Leeds United set to take their total outlay for Jean-Kevin Augustin to £40million, in return for just 48 minutes of service, the striker must now rank as the worst signing in the history of English football.

Augustin made only three substitute appearances for Leeds in 2020, after which the club argued their obligation to buy the player from Red Bull Leipzig had been invalidated by the Covid-19 pandemic causing a delay to the season’s end.

However, Leeds lost their case at the Court of Arbitration for Sport and later reached a settlement of £15.5m with Leipzig.

The legal disputes did not end there and, this week, they have been ordered by a FIFA panel to pay Augustin £24.5m for breach of contract. Leeds are planning an appeal.

Here, Sportsmail takes a look at the Premier League’s 10 worst signings when it comes to players who barely featured for the buying club. (Note: a maximum of five Premier League starts).

Leeds have been ordered to pay 'Jean-Kevin Augustin £24.5 million for breaching his contract'

10. Arthur Melo – (0 PL starts, 0 sub apps. £4m loan, Liverpool from Juventus, 2022-current)

It is likely we will never see the Brazilian in the Premier League, with Liverpool ready to send him back to Juventus having played only 13 minutes of a Champions League tie.

The Reds badly needed midfield reinforcement, and they certainly signed a bad one here. Arthur underwent thigh surgery in October but had not impressed to that point, even when playing 63 minutes versus Rochdale in the Papa Johns Trophy.

To think, he once played for Barcelona and Brazil before moving to Juventus for £65m. Another loan move beckons, for any club naive enough to take him.

9. Stephane Guivarc’h – (2 PL starts, 2 sub apps. £3.5m, Newcastle from Auxerre, 1998)

He arrived as a World Cup champion after winning successive golden boots in France but never played a minute for the man who signed him, Kenny Dalglish. By the time Guivarc’h was fit, Ruud Gullit was manager.

He did score on his debut against Liverpool in a 4-1 defeat but that was his only goal and, come November, he had been sold to Rangers, insisting on an escape clause in his contract given his nightmare experience at Newcastle.

Gullit just did not fancy him. That said, he didn’t rate Alan Shearer, either.

8. Dele Alli – (1 PL starts, 12 subs apps. Free, Everton from Tottenham, 2022-current)

There was a reluctance to include the 27-year-old, given he is still an Everton player and could yet prove a good signing. Then we realised how flawed that theory is – for Alli looks finished as a footballer at any level, never mind the Premier League.

It is safe to assume the £40m in add-ons that Everton must pay Spurs will never be leaving their bank account.

The problem they have is that he still has a year to run on his contract and, after returning injured this week from a disastrous loan spell in Turkey, don’t be surprised to see talks of a mutual termination begin.

Dele Alli has returned to Everton after his disastrous loan spell in Turkey came to an end

7. Milton Nunez – (0 PL starts, 1 sub apps. £1.6m, Sunderland from PAOK, 2000-2001)

There was much excitement when the Honduras striker was paraded on the pitch and performed a boxing routine, a nod to his nickname ‘Tyson’. Peter Reid said: ‘He has something I thought we were missing, that bit of extra pace up front.’

The Black Cats boss had his man. Or did he? It turns out they signed the wrong player. Sunderland, in fact, wanted Colombia striker Adolfo Valencia, who also played for Greek side PAOK.

It all ended in legal action with claims of Nunez being owned by a Uruguayan club at the time of his move. Sunderland believed they had been misled throughout.

During two seasons he played just 15 minutes of Premier League football. Still, at least he won cult-hero status for the shadow-boxing act, if nothing else.

6. Savio – (1 PL start, 9 sub apps. £9m, West Ham from Brescia, 2009)

With Craig Bellamy having joined Manchester City for £14m, it took West Ham one week to reinvest a club record £9m in Savio, an unknown 19-year-old who had scored just three times for Serie B side Brescia.

That was three more than he ever would score for the Hammers and, after six months and with the club having realised their error, he was sold to Fiorentina at a considerable loss.

He would not score a league goal for any club until 2014, when netting on his debut for FC Atyrau of Kazakhstan.

Amidst all of this he was jailed for a brief period in Thailand after reportedly faking his own kidnapping to obtain ransom money from his family.

Savio made just one Premier League start for West Ham despite being a club record signing

5. Davy Klaassen – (3 PL starts, 4 sub apps. £23.6m, Everton from Ajax, 2017-18)

The midfielder was signed at great expense by his Dutch compatriot Ronald Koeman.

However, he was sacked come October and later admitted to his ‘disappointment’ with Klaassen, who struggled with the ‘aggressiveness and tempo’ of the Premier League.

Koeman had already dropped him from the squad by the time of his dismissal. The Liverpool Echo recently ranked Klaassen as Everton’s worst signing since 2010, and there is fierce competition in that field.

4. Winston Bogarde – (2 PL starts, 7 sub apps. Free, Chelsea from Barcelona, 2000-2004)

When a player’s legacy is the following quote, you know the transfer has not worked out, at least not for the club.

‘This world is about money, so when you are offered those millions, you take them. Few people will ever earn so many. I am one of the few fortunates who do. I may be one of the worst buys in the history of the Premiership, but I don’t care’.

Indeed, the Holland defender spent a staggering four seasons on £40,000 per week at Stamford Bridge, happy to train and pick up his wages despite the club wanting him out.

There was even talk of him taking a private jet to training from his home in Holland to make sure he was not in breach of that lucrative contract, which earned him close to £10m in return for just two league starts.

3. Bebe – (0 PL starts, 2 sub apps. £7.4m, Man United from Vitoria de Guimaraes, 2010-2014)

Perhaps the most infamous signing in United’s Premier League history, especially given Sir Alex Ferguson later admitted he had never seen him play and took a recommendation from Carlos Queiroz, his former assistant.

Bebe had previously represented Portugal in the Homeless World Cup and it’s fair to say he never looked at home at Old Trafford, where the forward played just 75 minutes of Premier League football in four years.

The transfer was later investigated by Portuguese police as part of anti-corruption probe.

Bebe's transfer to Manchester United was later investigated as part of an anti-corruption probe

2. Danny Drinkwater – (5 PL starts, 7 sub apps. £35m, Chelsea from Leicester, 2017-2022)

It is remarkable to consider the England midfielder stayed five years at Stamford Bridge, making just five Premier League starts, and all of them in his first season.

He spent the entirety of his second campaign frozen out by Maurizio Sarri before a series of ill-fated loan moves which saw him make more headlines for his actions off the pitch than on it, including allegations of head-butting a team-mate and reportedly picking up an ankle injury following a nightclub altercation.

He has been without a club since his release from Chelsea in the summer and has expressed regret at ‘wasting’ what should have been the best years of his career.

1. Ricky Alvarez – (0 PL starts, 0 sub apps. £9.5m, Sunderland from Inter Milan, 2015)

The Argentina midfielder played 13 Premier League games during a loan spell before his move was made permanent on the condition Sunderland stayed up, which they did.

Except, Sunderland refused to honour that agreement after claiming a pre-existing injury in his left knee had caused a newly discovered issue in his right.

Alvarez instead joined Sampdoria but, in 2017 and after a long legal wrangle, Sunderland were ordered to pay Inter Milan a £9.5m transfer fee for a player they did not own.

To add to the bill, Alvarez successfully won a claim for £4.7m in lost earnings. The club continued to fight their case but eventually called it quits in 2021 having shelled out close to £20m in fees.

Sunderland were ordered to pay Inter Milan £9.5m for Ricky Alvarez following a legal dispute

P.S. Papy Djilobodji would be a prime candidate for our list given Chelsea paid £4m for the defender in 2015 and the very next day left him out of their 25-man Premier League squad.

However, within 12 months they had doubled their money on the Senegalese without him ever playing a game for the club. The buyers? Sunderland. Now why doesn’t that surprise us…

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