Top 10 Worst Premier League Signings of All Time
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Top 10 Worst Premier League Signings of All Time

Top 10 Worst Premier League Signings of All Time

Football transfers are notoriously uncertain things.

Massive money involved, some players will thrive, some will barely survive.

Okay, okay. That's maybe a little dramatic but still, a lot is on the line when a club signs a player.

It's fair to say that, when looking back over the history of transfers in the Premier League, there have been a fair few that haven't gone to plan... and that's to put it nicely in the case of some clubs cough cough Man United and Chelsea.

With that being said, it's always fun to have a little mooch back over the worst transfers of all-time, even if it does probably bring PTSD for a lot of fans - so here is our top 10 of the worst Premier League transfers of all-time.


10. Nicholas Pepe- £72m (Arsenal)

Pepe was by no means terrible for Arsenal, in fact his status as a flop was for a while debated quite heavily.

But I'm sorry, £72m for 16 goals and 9 assists in 80 games just isn't enough.

This is a classic case of the player actually being good, but the sheer size and inflation of the fee they are bought for making it almost impossible to live up to, and condemning them to failure from the very beginning.

Poor Pepe.


9. Alexis Sanchez- £35m + Henrikh Mikhitaryan

The best part about this is Manchester United thinking they'd had Arsenal's pants down when this move first happened... if anything Arsenal's pants were two sizes too tight, certainly not by their ankles.

Sanchez had set the world alight at both Barcelona and Arsenal before his move to Manchester, but, just like has become the norm these days, Man United once again ruined a career and Sanchez joined the rest of the unfortunate players at the Old Trafford graveyard.

Mkhitaryan, who went the other way, actually ended up having a tidy little career at Arsenal, before moving on and continuing his fruitful career.

Think it's clear who got the best of this one...


8. Tanguy Ndombele- £63m (Spurs)

This one brings a tear to the eye.

Ndombele could, and maybe should have been that guy. Instead, he's just a forgotten memory heading a list of 'what could have been' stories.

It actually pains me to put him here, but unfortunately his ability and talent wasn't enough to see him reach the top.

Fitness and work rate were his main downfalls, there were questions of attitude issues, which are largely unsubstantiated in fairness, and Ndombele appears to be just another baller who couldn't cope with the limelight of the world's biggest stage.


7. Kepa- £71.8m (Chelsea)

When Chelsea were looking for a goalkeeper in 2018, you would be forgiven for thinking they'd just gone out an picked the man with the most fitting name in Kepa.

And to be honest, I'm still not sure it was anything other than that.

To this day, the Spaniard holds the record as the most expensive goalkeeper of all time, and there aren't too many arguments to say he was worth the money paid.

When your most memorable moment is refusing to be substituted for a penalty shootout in a cup final... before losing the game anyway, it's difficult to see how you can't be considered a flop.

Kepa isn't higher on this list because he has actually showed himself to be a decent keeper in recent times, especially last season at Bournemouth... so think yourselves lucky here Chelsea.


6. Romelu Lukaku- £97.5m (Chelsea)

Chelsea's number 9 curse. A well known phenomenon, and perhaps no one has been more indicative of exactly that than Romelu Lukaku.

A club record fee off the back of a Champions League winning season for Chelsea, Lukaku was the jewel in the crown for the blues... or at least he was supposed to be.

You'd think being from Belgium Lukaku's goalscoring record would have been sweet like chocolate, instead it was more sour like milk- Ironically that's exactly how his transfer fee aged... like milk.

Big Rom was at the club from 2021-2024, he played 26 games and scored 8 goals- with fitness issues plaguing his spell.

An all round disaster it must be said.


5. Ricky Alvarez- £9.5m (Sunderland)

It always brings me such joy when I'm able to mention Sunderland in a negative list (as you can imagine I'm always joyful), so I searched far and wide for someone to include here- and I think I've found the perfect man for the job.

Imagine going to a restaurant and ordering food, only for that food to then be the wrong order. Then, instead of them taking the meal off the bill and giving you what you ordered, they still make you pay for the food and give your correct meal to someone else.

That is exactly what happened with Ricky Alvarez... bar the fact he is a human and not pub grub of course.

Sunderland loaned Alvarez from Inter Milan in 2014, agreeing to sign the player permanently should they avoid relegation.

And, you guessed it, Sunderland avoided relegation. Then came the drama.

The club refused to pay, claiming that pre-existing problems with his left knee, including new issues with his right knee, should void the obligation.

In fact, the Argentinian would then join Sampdoria on a free transfer... but Sunderland were still ordered to pay the £9.5m.

In return for the outlay they got, well... nothing.


4. Jean-Kevin Augustin- £15.5m (Leeds United)

Jean-Kevin Augustin to Leeds. Appears a pretty normal transfer, right?

Wrong.

What began as a pretty standard loan with an obligation to buy, ended with a heated dispute between clubs that left Leeds out of pocket for almost nothing in return.

The issue was, Covid hit. Something which Leeds argued should see the obligation voided due to the delay to the end of the season.

Unfortunately for them, nobody agreed and they had to pay the £15.5m fee anyway.

Well, surely that's fine if Augustin was good right?

Yeah, that would be the case... but Augustin actually only made three substitute appearances for a total of 48 minutes for Leeds.

Not quite sure that can be labelled as 'good'.


3. Antony- £81.3m (Manchester United)

The fidget spinner has arrived.

It's fair to say Eric Ten Hag's transfer dealings left a lot to be desired at Manchester United, perhaps none more so than Antony.

£81.3m for someone who, yes showed promise, but had only scored 8 league goals in the previous campaign for Ajax was absolutely insane on the face of it.

Well... not just on the face of it, it just was an insane decision.

Interestingly though, as is the way with almost every Man United signing these days, Antony has now moved on to Real Betis, and looks miles better than he ever did in red... what does that tell you?


2. Mykhailo Mudryk- £88.5m (Chelsea)

The third time Chelsea have appeared on this list... sort it out, lads.

A transfer scrap which initially saw fans laughing at Arsenal for losing out on the Ukranian's signature has, it's fair to say, become almost the exact opposite and Arsenal have no doubt dodged a bullet.

Mudryk only joined in 2023, looking at purely that you might think it's a bit harsh to already have him on this list.

But when you consider that he's currently facing a 4-year-ban for taking prohibited substances, you must admit it becomes difficult to argue with his inclusion.

And it gets worse when you think about the 8-year contract Chelsea have him on... they have literally paid for 4-years of ban.

Not exactly elite level business is it...


1. Ali Dia- Free Transfer (Southampton)

Ah yes, the man you've probably all been waiting for. Would it even be a failed transfer list if we didn't mention the most notorious of all time?

The only footballing top 10 Ali Dia will ever be on, never mind top of- but it's a pretty well deserved 1st place isn't it?

Here's the story...

A man rang Southampton up claiming to be George Weah. If you hadn't guessed... it wasn't.

The man recommended Ali Dia to the club, claiming an elaborate past career where he had played with Weah at PSG.

Instead of, you know, actually doing some research and verifying the status of Ali Dia, manager Graeme Souness fell for the rouse.

Dia was granted a trial at the club, where he was somehow signed, before making an absolutely abhorrent debut- never to be seen again.

Absolute madness, but story worthy of footballing royalty nonetheless.

Benji Kosartiyer
Journalist

Matty Connelly

Content Writer

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