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Over two spells in west London he signed names such as Mateja Kezman, Jiri Jarosik and Juan Cuadrado for not inconsiderable sums, only to see each fall flat on their faces in the Chelsea shirt. Players such as Maniche, Marco van Ginkel and Loic Remy were also failures at Stamford Bridge, while the £2.7 million purchase of Papy Djilobodji from Nantes in 2015 goes down as one of the most bizarre moves of Mourinho’s career.
At Madrid, too, Mourinho failed to make the best of great talents, with Pedro Leon and Fabio Coentrao notable flops under the Portuguese. And while the 53-year-old spent two successful seasons in Italy with Inter, building a formidable treble-winning side in his second campaign, it was not without a few hiccups along the way.
The €13m move for Roma’s Amantino Mancini quickly turned into an unmitigated disaster, while a further €13m went on the signing of Cagliari forward David Suazo. Inter even battled Milan behind the scenes to land a player who would go on to score only eight times in 41 appearances for the club.
Undoubtedly the stand-out failure in the market at San Siro was the €24.6m splash on Porto’s Ricardo Quaresma, who would play only 24 times for the Nerazzurri. While he wasn’t wanted by the board, Mourinho insisted on them paying out for his compatriot. “I respect their opinion on Quaresma, but mine is different,” said Mourinho. “His pace, his quality, his dribbling could be very useful and I have been saying this for months.”
It didn’t take long, though, for the coach to realise his mistake, and Quaresma was soon ostracised by Mourinho for his tendency to shirk hard work. “My biggest regret was joining Inter,” the winger admitted later. “My happiness and self-confidence were taken away from me. At one point I wasn’t even called up any more. I felt on the margins of the squad and woke up crying when I had to attend training sessions.”
He has become prone to giving up on potential superstars too, especially during his most recent spell at Chelsea. The decision to sell Kevin De Bruyne to Wolfsburg after only five starts in the blue shirt was soon made to look foolish thanks to the Belgian’s fantastic form in Germany which would later earn him a £57m move to Manchester City.
Romelu Lukaku and, notably, Juan Mata are others who have found their road into the Chelsea first team blocked by Mourinho, with the Spaniard in particular being left feeling hard done by following back-to-back Player of the Year awards. His exclusion on the grounds of not doing enough work off the ball soon led to a transfer to Manchester United, and Mata must now wonder what the future holds with his former foe rocking up at Old Trafford.
A fail transfer window is pretty much guaranteed.