Jose Mourinho’s ten worst career signings, with latest Chelsea flop Juan Cuadrado & strange Real Madrid loan

With Chelsea’s big-name January signing Juan Cuadrado looking like another strange purchase by the Blues, here’s a look at the worst ever transfers by manager Jose Mourinho, including others at his previous clubs Real Madrid and Inter Milan…

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Chelsea transfer rumours

1) Juan Cuadrado

Making absolutely no impact at Chelsea so far since joining from Fiorentina in January, Juan Cuadrado looks another big mistake by the Blues, who let Mohamed Salah join the Italian side on loan in return – he, unlike the Colombian, has been excellent since the move.

2) Andriy Shevchenko

Perhaps not Mourinho’s choice, but the previously world class striker Andriy Shevchenko looked far worse after swapping AC Milan for Chelsea in 2006, going down as one of the biggest Premier League flops of all time.

3) Mateja Kezman

Another poor buy by Mourinho in his first Chelsea spell, Mateja Kezman fought with Didier Drogba for a place upfront at Stamford Bridge – one proving considerably more successful than the other.

4) Asier Del Horno

Signed a year before Chelsea finally landed Ashley Cole, Asier Del Horno was clearly a stop-gap signing at left-back, and did precious little in his only season with the Blues.

5) Steve Sidwell

He may have been a free transfer after seeing out his contract with Reading, but Steve Sidwell still looks a waste of money after an ineffective season at Stamford Bridge, spending the rest of his career with relegation-fighting clubs like Aston Villa and Fulham.

6) Nuri Sahin

Also known for being a total flop in a brief stint with Liverpool, Nuri Sahin was a strange signing by Mourinho during his time at Real Madrid, barely playing and clearly not proving much of a talent elsewhere.

7) Emmanuel Adebayor

Bizarrely signed on loan from Manchester City, Emmanuel Adebayor spent half a season playing under Mourinho at Real Madrid, and actually fared quite well, though he clearly wouldn’t have been a good choice to bring in permanently.

8) Ricardo Quaresma

Long regarded as a wasted talent, Ricardo Quaresma was given a chance to shine under Mourinho at Inter Milan, but it’s fair to say the Portuguese winger didn’t take it.

9) Michael Essien

A great signing by Mourinho at Chelsea, but a pretty useless one by the time he brought him in on loan at Real Madrid. The incredibly injury-prone midfielder was past his best by that point and did little in his time at the Bernabeu.

10) Hamit Altintop

A very average player, Hamit Altintop was another strange Real Madrid signing by Mourinho, who clearly didn’t quite get the ‘Galactico’ policy adopted by the Spanish giants.