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Top 10 worst Premier League signings of all time

Damien Kayat looks at the top 10 worst Premier League signings of all time.

Alexis Sanchez - Premier League
Image Copyright - Steve Haag Sports

Damien Kayat takes a look the 10 worst signings in Premier League history.

Two women looking excitedly at cellphone

‘It’s coming home’. Those words will haunt the collective English consciousness for some time to come. Club allegiance will now take centre stage, as fans turn to the machinations of the transfer market for some retail therapy. I’ve decided to lighten the mood with a ranking of the Premier League’s top 10 worst ever signings. Obviously this is entirely subjective and absurdly arbitrary. I could just as easily have included Fernando Torres’ Chelsea fiasco (though those crucial European goals probably shield him from the ignominy of this list). Nevertheless, here goes nothing.

10. Karel Poborsky
1996- From Slavia Prague to Manchester United for £3.5 million

I’m starting this list with a slight fib. The likes of Alberto Aquilani and Jordi Cruyff are probably more deserving of this rogues’ gallery. I just had to shoehorn Poborsky into this list as a post-Euros cautionary tale.

There’s a tendency for clubs to get feverish in the wake of huge tournaments (there are even a few deluded Arsenal fans who are now questioning the sale of Granit Xhaka). Karel Poborsky was an integral member of the Czech side that reached the 1996 Euros Final.

Sir Alex Ferguson probably envisaged him as a ready-made replacement for the recently departed Andriy Kanchelskis. But the Czech winger failed to acclimatize to the frenzied pace of the league, highlighting the perils of cherry-picking players based on their performance in a major tournament.

It didn’t help Poborsky that a certain David Beckham began to rise to prominence during this very period.

9. Dennis Wise
2001- From Chelsea to Leicester City for £3.2 million 

The man with the ironic surname (sounds like a hastily rejected Bond film). A twilight-era signing can offer a club great value. You get to harness the experience of a grizzled pro, trusting that he would impart some wisdom to the younglings in the squad.

Just look at how much Craig Dawson galvanized West Ham’s defence last season. Dennis Wise doesn’t fit into that category. Firebrands such as Wise don’t age as gracefully as the Michael Carrick’s of this world. Never the most mobile midfielder, Wise was fundamentally a generic version of Roy Keane: tidy on offence but enthusiastic in defence.

The 35-year-old was jaded when he joined the Foxes, worn thin by his combative trickster persona. He ‘mentored’ a Leicester side to relegation in his first season. But he hadn’t finished sullying his reputation just yet.

He punched Callum Davidson in the face at the following season’s summer training camp, breaking the Scottish international’s cheekbone. This pathetic moment of Peaky Blinders lunacy was apparently triggered by a card-game dispute.

He was released from the squad and the club soon entered administration. And absolutely no one was the wiser.

8. Bebe
2010- From Vitoria Guimaraes to Manchester United for £7.9 million 

This signing lands squarely at Carlos Quiroz’s door (a joy to Roy Keane’s ears, no doubt). Sir Alex Ferguson would later admit that he signed Bebe having never seen him play, relying on the advice of Quiroz.

Following the unparalleled success of Cristiano Ronaldo and the more modest high-jinks of Nani, United were banking on Bebe to be yet another flying Portuguese winger.

Little did they know that they had purchased arguably the worst player to ever don the famous Red Devils logo. He would only play 75 league minutes for United, consistently overcooking crosses in amateurish fashion.

This was a ludicrous signing from the get. Bebe had never previously played above the 3rd tier in Portuguese football. He nearly represented Portugal at the Homeless World Cup. I kid you not.

This story never had a happy ending, with Bebe stating that he should have rather stayed at his orphanage than join United.

7. Saido Berahino
2017- From West Brom to Stoke City for £12.5 million 

Pride comes before the fall. This is a classic case of an entitled, young English player who should have learned to walk before he could fly.

Berahino was once a highly talented prospect, lighting up the Hawthornes with his pace and finishing capabilities. There was more than a shade of Raheem Sterling in Berahino.

But Berahino was impatient, threatening to go on strike if Tony Pulis wouldn’t let him go to Spurs. His lack of professionalism left Pulis in a state of perpetual speechlessness. He severely hamstrung West Brom prior to his £12.5 million move to Stoke City.

It was at Stoke City where this prima donna ultimately saw his flame burn out. Berahnino failed to score a single goal in 28 matches in his first season for the Potters.

This was arguably the single biggest factor in their relegation. He then scored just three goals in the 2nd tier of English football before a drunk driving charge got him booted from the side.

6. Danny Drinkwater
2017- From Leicester City to Chelsea for £34.1 million pounds

Drinkwater’s story has a Shakespearean trajectory, veering from joy to tragedy to absolute farce. Playing alongside N’Golo Kante, Drinkwater formed part of the midfield core that propelled Leicester City to their fairy-tale Premier League title.

In retrospect, winning that title alongside Drinkwater is possibly the greatest indicator of N’Golo Kante’s midfield mastery. Drinkwater’s torrid spell at Chelsea started with an air of desperation, as the London giants were initially unable to secure the services of Ross Barkley (look how that ultimately turned out).

He only made 12 appearances in his debut season under Conte before being completely ostracized by both Sarri and Lampard. His loan spells have proved even more disastrous, evoking images of Joey Barton in his pomp.

His Burnley spell was highlighted by an injury sustained in a nightclub brawl while his Villa stay ended with him being shipped back to Chelsea for headbutting a teammate. He is now on loan at Turkish side Kasimpasa (‘on loan in Turkey’ is essentially the launch code for detonating careers).

5. Andriy Shevchenko
2006- From AC Milan to Chelsea for £39.5 million 

This one is especially significant as it came to personify the growing schism between two of the Premier League’s most influential figures: Roman Abramovich and Jose Mourinho.

The Ukrainian marksman was one of the most celebrated strikers in European football when he joined the Blues in 2006. This was a dream come true for Abramovich, who viewed Shevchenko as the messianic figure who would propel Chelsea to European Cup success.

It wasn’t to be, as the Ukrainian was a shadow of his former self in London. The gulf in tempo between Italian football and English football is perfectly encapsulated in the Shevchenko saga. Mourinho ultimately played him out of position to accommodate figurehead Didier Drogba.

This didn’t go down well with Abramovich, with many identifying the Shevchenko issue as a core reason for Mourinho’s termination in 2007. The Ukrainian scored just 9 goals in 48 games whilst operating in an elite Chelsea outfit.

English football wasn’t done with Shevchenko. Now the Ukrainian national coach, Shevchenko had to endure the humiliation of a 4-0 Euros quarterfinal defeat to England. I don’t think ‘God Save the Queen’ will feature on his iTunes playlist.

Two women looking excitedly at cellphone

4. Alexis Sanchez
2018- From Arsenal to Man United in a swap deal for Henrikh Mkhitaryan

There does seem to be something absurd about having three United players on this list. How could the most successful club in the Premier League’s history be the home of so many turkeys?

The answer is really baked into the question. United’s outrageous level of success in the modern era lends more scrutiny to new arrivals, and any ineptitude is magnified by the club’s grand legacy.

Sanchez was signed by Jose Mourinho as the ostensible replacement for Zlatan Ibrahimovic. He greeted the United faithful with a cringe-worthy rendition of ‘Glory, Glory Man United’ (on piano, no less).

He obviously forgot the sheet music from that point on. Nothing worked. Injuries and poor form dogged the Chilean from the start. He also lacked the athleticism to fit into Ole Gunnar Solksjaer’s counterattacking style.

He scored five goals in 45 matches for the Red Devils. He was ultimately loaned out to Inter who eventually signed him on a free.

3. Tomas Brolin
1995- From Parma to Leeds United for £4.5 million 

‘Affectionately’ known as ‘Tubby Tom’ by Leeds supporters, Tomas Brolin was identified as the midfield foil for striker Tony Yeboah. In the early 90’s, Brolin was one of the hottest properties in world football.

He finished 4th in the 1994 Ballon d’or after starring for Sweden at the World Cup. He had also been a vital cog in the Parma side that won the European Cup Winners Cup. He sustained a major ankle injury in 1994 but that did not dissuade the Leeds hierarchy from signing the effervescent talent.

He arrived in England with some puppy fat and never really managed to shake it. Howard Wilkinson soon became frustrated with his unwillingness to track back. Wilkinson was replaced by none other than George Graham, which was really a nightmare scenario for the showboating Swede.

Graham was an arch-pragmatist who demanded absolute professionalism from his players (boring, boring Arsenal and all that jazz). The final straw in their relationship is the stuff of Monty Python legend. Brolin failed to report for training after a bird apparently flew into his windscreen, preventing him from catching a plane to England.

The Swedish media published images of his broken windshield with some speculating that he may have hit an elk. Either way, the English media lambasted him and his time as a Leeds player was essentially over.

2. Mario Balotelli
2014- From AC Milan to Liverpool for £18 million

You can’t really have a list that gleefully embraces folly without Mario Balotelli. This great enigma provided the most important assist in Premier League history, calmly feeding the ball into Sergio Aguero’s path in that monumental match against QPR.

But he is largely remembered for his erratic behaviour and sense of mischief. Who can forget Balotelli carelessly backheeling the ball past the posts with an empty net at his mercy in a pre-season friendly? Roberto Mancini won’t.

But Brendon Rodgers needed a replacement for Luiz Suarez and Balotelli had just scored 14 goals for AC Milan in his previous campaign. Unfortunately, Rodgers failed to inherit any of the Italian’s positive qualities and was burdened with an idle trickster with zero motivation.

Balotelli scored one Premier League goal in 939 minutes for the Merseyside giants. He was eventually released to Nice on a free. Still, there’s something oddly endearing about Balotelli’s brand of laconic narcissism. Just watch Mourinho’s face when the subject of Mario Balotelli comes up.

Regardless of how scandalous the context, there is a unique warmth in his expression that seems reserved for the mercurial Italian.

1. Ali Dia
1996- signed on a free from Imagination Land

We live in an age where technology has turned everyone into a footballing guru. One look at YouTube will show you just how many ‘experts’ we have in our midst, routinely discussing obscure Ligue 1 players with absolute authority.

So, there is something extremely romantic about this story, one that shares more DNA with a Will Ferrell comedy than a football transfer. Someone phoned Southampton manager Graeme Souness pretending to be George Weah (who at that time was the FIFA World Player of the Year).

The cheeky fraudster implored Souness to look into his cousin who had supposedly played alongside him at Paris St Germain. Much to their dismay (and to our eternal gratitude), Southampton never did their due diligence and signed 31-year-old college student (and part-time footballer) Ali Dia.

It was the greatest hoax perpetrated in footballing history. He even managed to get 53 minutes of Premier League game time before Souness realised that he had been sold a lemon.

It’s symbolic of an era where clubs still had a semblance of human relatability, where the boundaries between players and fans hadn’t become completely fortified by the machine that is modern professional football.

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