Nobody in the world of sports, regardless of how successful or how respected that person has been, gets everything right all of the time. Bill Belichick is revered as maybe the greatest coach in the history of the National Football League. Belichick and the New England Patriots decided to give tight end Aaron Hernandez a chance to play in the NFL. We all know how that worked out. Phil Jackson would, if he was being honest about his career in the National Basketball Association, have to admit that he has been guilty of plenty of poor decisions that have negatively affected teams.
Nobody can deny that Jose Mourinho has been a phenomenal manager for multiple clubs over the years. Just look at his resume and examine the titles that Mourinho has won if you have any doubts about his track record. Mourinho has been responsible for many smart signings and transfers that have built squads capable of contending for league titles and Champions League trophies. Odds are that Mourinho would have his pick of a job were he to become available at some point in 2015 or 2016, largely because he has a history of being a hit for a team in need of some life from a manager.
Mourinho could soon find himself looking for another gig if he is unable to turn Chelsea around during the 2015-16 Premier League campaign. It would not be the first time that Mourinho and the club have parted ways, and it would also not be the first time that errors made by Mourinho proved to be costly. Mourinho, like every great manager before him, has been guilty of completing some questionable and even bad signings over the years. Nobody is perfect, not even a man who was once given the nickname “The Special One.” It seems like it was long ago when Mourinho first earned that label.
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15 Emmanuel Adebayor
The striker who fell out of favor with multiple Premier League clubs had an opportunity to play under Mourinho at Real Madrid via a short loan move that began in January 2011. It was a curious move in that Mourinho had to have known of Adebayor's reputation for growing tired of his surroundings and for allegedly not always giving full efforts during matches. Adebayor was not a horrible player while at Real, but he also never came close to securing himself a full-time job with the club. This decision by Mourinho remains a head-scratcher even years after the fact.
14 Steve Sidwell
One may consider leaving Steve Sidwell off of this list entirely because he joined Mourinho and Chelsea via a free transfer in the summer of 2007. The reason that Sidwell makes the cut is because it did not take long for everybody, Mourinho included, to see that Sidwell was not good enough to earn minutes for Chelsea. Acquiring Sidwell was not a complete bust for Mourinho and for Chelsea, as the club did receive an undisclosed transfer fee when the player was sold to Aston Villa. After leaving Chelsea, Sidwell was little more than a middle-of-the-road player.
13 Khalid Boulahrouz
Khalid Boulahrouz was a versatile defender who could fill in for Mourinho at several positions. The problem was that Boulahrouz was not good enough to start ahead of others who were in that Chelsea team. Mourinho decided to move on from Boulahrouz after a single season, and he loaned the player out for the 2007-08 campaign. Boulahrouz never again played for Chelsea, and he has not since started for a club as massive as Chelsea. While the reported transfer fee of £9.24 million is not a crazy amount of money in the current landscape, it is still a lot to spend on a flop.
12 Nuri Sahin
Those who focus on the bad signings that Mourinho has made while being the boss at Chelsea may have had this one slip from their memories. Nuri Sahin left Borussia Dortmund to join up with Mourinho and Real Madrid before the 2011-12 season. That experiment was ended after Sahin had played in only a handful of matches for Real. Sahin was loaned out to Liverpool, where he was more of a disappointment than he was a star player. Sahin was a bust for Real and for Liverpool, and his time spent with Mourinho at Real is now but a memory.
11 Tal Ben Haim
Tal Ben Haim was thought, at the time, to be a man who could play multiple positions in Mourinho's Chelsea lineup. Ben Haim was able to be a fill-in when Mourinho needed his services, but the Israeli international was unable to earn first-team football when better options were available. The decision to bring Ben Haim to Chelsea was made to look even worse when the player became a journeyman in English football. Ben Haim was a poor Mourinho signing even before Manchester City learned that he did not have the necessary quality to play for a championship contender.
Tiago was not a complete bust for Mourinho. The midfielder did, after all, make 34 appearances for Chelsea during his single season with the club. There are, however, reasons why Tiago was a one-and-done signing. Mourinho realized, after one campaign, that he needed an upgrade at the position, and he found just that when he was able to acquire Michael Essien. Essien was, no disrespect meant, the better option for Chelsea and for Mourinho. With his playing time cut due to the arrival of Essien, Tiago departed Chelsea and signed with Lyon.
9 Asier del Horno
Asier del Horno was acquired by Mourinho in June 2005. The left back ended up being nothing more than a transitional player for Chelsea. Del Horno had been with the club for a single season when Mourinho completed the long process of acquiring Ashley Cole. That signing made Del Horno a backup option and Mourinho allowed the player to move on from the club during the 2006 summer transfer window. While it is fair to say that not every transfer is going to be a gem for a manager, Del Horno deserves to be mentioned as one of the worst signings that Mourinho has made.
8 Jiri Jarosik
It is, in a way, somewhat baffling that an accomplished manager such as Mourinho has managed to be responsible for so many curious midfield signings. Jiri Jarosik, also capable of featuring as a defender, managed to pick up enough appearances during his very brief run with the club that he earned a championship medal after Chelsea won the Premier League title. That is about where the story ends as it pertains to Jarosik's time with Chelsea. Jarosik was loaned out to Birmingham City less than a year after he joined Chelsea and he was later sold to Celtic.
7 Michael Essien
Michael Essien was, when at his best, a noteworthy talent who could play at several positions on the pitch. By the time that Essien linked back up with Mourinho at Real Madrid, though, the player had been slowed by injuries and by the wear and tear that comes with being a professional footballer for a significant length of time. Essien failed to make much of an impact during his brief stint with Real and he could be considered one of the most lackluster signings that the team has made in recent memory. Mourinho could not recover magic that had been lost in this case.
6 Mateja Kezman
Mateja Kezman and Didier Drogba were both strikers who played for Chelsea. That is about all that the two shared while featuring for Mourinho at the club. Kezman was such a bust for the club that even he has, in interviews, discussed that he was a letdown for Mourinho and Chelsea. His lack of success did not, per Sky Sports, take away from the fact that Kezman loved his time at Chelsea:
"Living and playing in London was something that I will never forget.
"I don't know if I made a mistake because I moved away so quickly. Maybe I do and maybe I don't regret it, but I always believe in my decisions.
"But the transfer to Chelsea made my dreams come true. That was the best thing that ever happened to me.
"Maybe I could achieve more and I could have been more successful at Stamford Bridge, but I don't regret anything."
5 Fabio Coentrao
Mourinho likely hoped that he had landed a man who could start as a fullback or a winger when he signed Fabio Coentrao. What Mourinho instead got was a player who was nearly sold to Tottenham Hotspur two years after he joined Real Madrid. Coentrao became surplus to requirements, in part because of injury woes, after Mourinho left Real, and the player has been loaned out. While there is still time for Coentrao to make an impact for the Spanish giants, it instead appears more likely that he will be a regrettable signing made by Mourinho.
4 Shaun Wright-Phillips
There are some cases where fans are simply left shaking their heads about the amounts of money that clubs have spent on players over the years. Shaun Wright-Phillips was once acquired by a reported transfer fee of £22 million. That ended up being an absurd amount of money for a man who was little more than a backup option for Mourinho at Chelsea. Wright-Phillips was, as harsh as it may be to say, not good enough to routinely start for Premier League squads. He ultimately fell out of favor at Chelsea and Manchester City, and he eventually found himself as a reserve player for Queens Park Rangers.
3 Juan Cuadrado
The sun has not yet set on this transfer, but all indications are that Juan Cuadrado will be among the lists of the worst signings ever made by Mourinho. Mourinho acquired the services of Cuadrado during the January 2015 transfer window and the player has thus far made no impact for Chelsea. Cuadrado is currently on loan at Juventus and he will likely make a permanent exit from Chelsea if Mourinho is shown the door by the club at some point before the spring of 2016. We could, in future days, refer to Cuadrado as maybe the worst signing Mourinho made during his return to Chelsea.
2 Didier Drogba
Didier Drogba is a Chelsea legend who is beloved by supporters. Drogba was also in the twilight of his career when Mourinho brought him back to the club in 2014. While Drogba certainly was not expected to be the player of old during his final stint with Chelsea, Mourinho could have gone with a different and younger option ahead of the 36-year-old striker. The first name that comes to mind is Romelu Lukaku, who was never given a true chance to shine under Mourinho. It could turn out that the Drogba will be a reminder to Mourinho that the devil you know is not always better than the devil you don't.
1 Andriy Shevchenko
The immediate hot take that Mourinho defenders will have upon seeing this name is that Andriy Shevchenko was a signing made by Chelsea chairman Roman Abramovich and not the manager. That may or not may not have been the case, but it is Mourinho who will, whether he likes it or not, have his name linked with the goal-scorer who was a flop during his stint with the Premier League outfit. Shevchenko never looked like a Ballon d'Or candidate while he was wearing Chelsea blue and his signing is right there among the worst in the history of the EPL.
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