Jose Mourinho's worst ever signings - ranked

Even Mourinho's had some stinkers
Even Mourinho's had some stinkers / Alex Livesey/Getty Images
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Jose Mourinho has hardly had to scour the bargain bucket when it comes to signing players throughout his illustrious managerial career, but it would be amiss to just ignore some of the great purchases he's overseen.

That being said, he's not averse to the odd clanger, either.

Gedson Fernandes was recently recalled from Tottenham by his parent club Benfica, after the Portugal international endured what can only be described as a nightmare spell in north London.

So where does Fernandes rank in the list of 'The Special One's' worst ever signings? Prepare to cringe and have your eyes water as we look at his worst ever buys.


15. Steve Sidwell

Steve Sidwell lasted just one year at Chelsea
Steve Sidwell lasted just one year at Chelsea / Shaun Botterill/Getty Images

Steve Sidwell was never going to trouble the top spots in our list of Mourinho's worst ever signings considering he arrived at Stamford Bridge on a free transfer... but he was pretty out of place.

The former Reading man completed 90 minutes of league football just twice in his time at Chelsea, failing to even make the matchday squad for the final 13 rounds of Premier League matches.


14. Asier del Horno

Asier del Horno squares up to Steven Gerrard
Asier del Horno squares up to Steven Gerrard / ANDREW YATES/Getty Images

Here we go. Now we're slowly creeping up the valuation ladder.

Asier del Horno arrived at Stamford Bridge in 2005 for around £8m. The idea was that the Athletic Club left-back would be a step up from Wayne Bridge and Chelsea could look to challenge on the European front as well as domestically.

The only slight problem was that he was absolutely useless. In all honesty it's a travesty he left the club with a Premier League winner's medal.


13. Khalid Boulahrouz

Khalid Boulahrouz' Chelsea career never really got going
Khalid Boulahrouz' Chelsea career never really got going / Etsuo Hara/Getty Images

The Chelsea number nine shirt has become something of a poisoned chalice since the arrival of Roman Abramovich - an issue we'll come to shortly.

But when you think of Chelsea's failed number nines, Khalid Boulahrouz isn't the first name that springs to mind. Sure, he didn't play in the number nine position - but he was given the shirt number for some weird reason.

The £8.5m defender spent two years at Stamford Bridge and managed just 13 league appearances before being shipped off to Stuttgart.


12. Filipe Luis

Filipe Luis is another failed Chelsea left-back under Mourinho
Filipe Luis is another failed Chelsea left-back under Mourinho / Julian Finney/Getty Images

Did Mourinho actually make any good Chelsea signings?

Next up on our list of rubbish signings is Filipe Luis. The Brazilian is a weird one in the sense that he isn't actually a bad player - he was just rubbish for Chelsea. Although, to be fair, that's probably true of pretty much every player on this list (barring Khalid Boulahrouz).

Luis failed to make an impact in west London and was soon sold back to Atletico Madrid after just a year in England.


11. Radamel Falcao

Radamel Falcao failed to produce at Stamford Bridge
Radamel Falcao failed to produce at Stamford Bridge / Jordan Mansfield/Getty Images

The misfiring frontman had previously failed to produce the goods during a year-long loan with Manchester United, but if anyone could get him back to his best then surely it would be Mourinho, right?

That worked out well.

A solitary goal in 12 appearances in all competitions, but perhaps what was even more depressing was the fact he just didn't seem bothered.

Not exactly a costly purchase but an absolutely useless one to say the very least.


10. Ricardo Quaresma

Ricardo Quaresma had a miserable stay in Milan
Ricardo Quaresma had a miserable stay in Milan / Massimo Cebrelli/Getty Images

FINALLY, A NON-CHELSEA SIGNING.

Weirdly Ricardo Quaresma actually spent a year on loan with the Blues during Mourinho's Inter tenure, after the Portuguese tactician figured out that his countryman was absolutely useless.

Gone was the player who was tearing defences apart with ease at Porto, and in his place stood a midfielder completely bereft of ideas who genuinely just didn't seem to have the stomach for the fight.

Inter soon got shot of the winger as he signed for Besiktas in 2010 having mustered just one goal for the Serie A club.


9. Jiri Jarosik

Jiri Jarosik picked up a Premier League winner's medal at Chelsea
Jiri Jarosik picked up a Premier League winner's medal at Chelsea / Phil Cole/Getty Images

Anyone who even remotely follows English football should be able to name the majority of Chelsea's 2004/05 squad.

The Blues romped to their maiden Premier League crown in Mourinho's first year at the club, but there's one man who you could be forgiven for forgetting.

Jiri Jarosik arrived at Stamford Bridge midway through Mourinho's first year with Chelsea, and to put it mildly - he was crap.

Still, he managed to pick up a Premier League winner's medal before moving to Birmingham just eight months after he arrived. Not a bad little stop in the capital.


8. Nuri Sahin

Nuri Sahin during his time with Real Madrid
Nuri Sahin during his time with Real Madrid / Angel Martinez/Getty Images

Nuri Sahin was signed by Mourinho for Real Madrid in 2011, with the German arriving for a figure believed to be in the region of £9m.

In three years at the Santiago Bernabeu, Sahin made four La Liga appearances. Four. In three years. That's pretty impressive.

The midfielder spent the majority of his time with Real shipped out on loan before eventually securing a permanent move to Borussia Dortmund.


7. Papy Djilobodji

Papy Djilobodji didn't make a league appearance for Chelsea
Papy Djilobodji didn't make a league appearance for Chelsea / Matej Divizna/Getty Images

Alright, so turns out Chelsea actually made a profit on Papy Djilobodji, but we're not letting Sunderland's ineptitude let Mourinho off the hook for this shocking deal.

The Senegal international made one appearance for Chelsea in his year with
the club - a 59-second cameo against Walsall in the Carabao Cup in which he touched the ball twice.

For comedy reasons alone he makes it into the top 7.


6. Baba Rahman

Baba Rahman is yet to repay the fee Chelsea paid for him
Baba Rahman is yet to repay the fee Chelsea paid for him / Srdjan Stevanovic/Getty Images

Ahhh Chelsea's forgotten men.

You could name a full 25-man squad of players who Chelsea spent big money on and have subsequently just left to float aimlessly from loan move to loan move.

Baba Rahman may yet come good at Stamford Bridge, but let's be honest - it's highly unlikely.

The Ghana international makes his way onto our list having been signed for a whopping £14m by Mourinho in 2015, with five loans spells since meaning he's managed just 15 league appearances for the Blues.


5. Fabio Coentrao

Fabio Coentrao spent seven years with Real
Fabio Coentrao spent seven years with Real / Jean Catuffe/Getty Images

When Real Madrid signed Fabio Coentrao from Benfica in 2011, he was being talked of as one of the next big things in European football - it's fair to say they didn't quite get value for money in the €30m move.

The Portuguese left-back would make just 58 La Liga appearances in his seven years in Madrid, being shipped out on loan multiple times before eventually moving to former club Rio Ave in 2018.


4. Mateja Kezman

Mateja Kezman couldn't maintain his Eredivisie form in the Premier League
Mateja Kezman couldn't maintain his Eredivisie form in the Premier League / Ben Radford/Getty Images

When you think of Chelsea's failed number nines, there aren't many names that spring to mind ahead of Mateja Kezman's.

Having looked absolutely unstoppable in the Eredivisie with PSV Eindhoven, Kezman couldn't adapt to English football and left the club after just a year having notched seven in 41 games.

Not the worst strike record and not a particularly expensive deal - but a rubbish signing nonetheless.


3. Gedson Fernandes

Gedson Fernandes was barely given a chance at Spurs
Gedson Fernandes was barely given a chance at Spurs / Marc Atkins/Getty Images

Gedson Fernandes: the latest addition to the list of Mourinho's transfer mistakes.

With a whole host of clubs apparently vying for his signature prior to his Spurs arrival and a fee of around £45m agreed for the Portugal international, it's difficult to see why Mourinho just didn't fancy him.

But, fancy him he did not, and Fernandes heads back to Benfica having made just 12 appearances for Tottenham in all competitions.


2. Alexis Sanchez

Alexis Sanchez's career has gone downhill since leaving Arsenal
Alexis Sanchez's career has gone downhill since leaving Arsenal / Ben Early/Getty Images

The Alexis Sanchez of Arsenal and the Alexis Sanchez of Manchester United could not have been more contrasting players.

It would be unfair to blame Mourinho on the Chile international's demise considering he's been utterly hopeless at every other club he's since represented, but his move to Manchester United certainly seemed to spark his slump.

We'll probably never know what caused his sudden drop in form, but he undoubtedly falls into the category of one of Mourinho's worst ever signings.


1. Andriy Shevchenko

Andriy Shevchenko couldn't repay the huge fee Chelsea paid for him
Andriy Shevchenko couldn't repay the huge fee Chelsea paid for him / Getty Images/Getty Images

Alright, alright, we know - he was more of an Abramovich signing than a Mourinho signing, but as a top class manager you need to be able to get the best out of what you're given.

The prolific Ukrainian arrived at Stamford Bridge for a whopping £30.8m (we promise that used to be a lot of money back in 2006), but for some reason his Chelsea career just never took off.

Of all the club's torrid number nines, Shevchenko ranks amongst the worst and he's surely the worst signing of Jose Mourinho's career.