Jose Mourinho is undoubtedly a managerial great – when you manage clubs like Real Madrid, Inter and Chelsea, spending daft amounts of money comes with the territory.
The Portuguese’s two spells at Chelsea brought the club incredible success, including some of the most important transfers in the club’s history.
Didier Drogba, Ricardo Carvalho and Cesc Fabregas are all players Mourinho helped lure to west London, but for every hit, there were a couple of misses.
And with the January transfer window fast approaching, Football FanCast has taken a look at Mourinho’s top 10 worst Chelsea signings.
11 stars Chelsea will rue selling, including £172k talent now £82m
Chelsea have made some huge mistakes in letting these players leave, we at Football FanCast have taken a look.
ByFinley Harlow 10 Steve Sidwell Free from Reading, 2007
This one might be a little harsh. Steve Sidwell had a solid career, featuring heavily for fellow London clubs Reading and Fulham, while he established himself as a Premier League mainstay. His move to Chelsea was just a bit of an odd one.
Financially, it made sense. Sidwell joined on a free transfer from Reading, who had been yo-yo-ing between the Championship and the Premier League at the time, but he was never going to become more than a squad player at Stamford Bridge.
The midfielder only completed 90 minutes twice during his time at Chelsea despite featuring 25 times in the 2007/08 season. He did manage to score a goal in a 4-0 League Cup win against Hull City, but other than that, he didn’t make much of a mark.
He was sold to Aston Villa in the summer of 2008 for a fee believed to be in the region of £5m, so Chelsea did make a tidy profit.
Interestingly, he was given the number 9 shirt at Chelsea – something that will feature heavily in this list.
9 Khalid Boulahrouz £6m from Hamburg, 2006
Again, another weird Chelsea number 9. Dutch defender Khalid Boulahrouz inherited the seemingly cursed shirt number from Hernan Crespo. The Argentine may not have been amazing at Chelsea, but that’s quite a downgrade.
Even before he signed for the club, Mourinho pretty much admitted Boulahrouz wouldn’t be more than a squad player. Eventually, he was signed for a fee thought to be around £6m from German giants Hamburg in August 2006.
To be fair to Boulahrouz, he had a promising start to his Chelsea career, featuring heavily early on, including a solid defensive display against fellow top-four rivals Liverpool.
Unfortunately, a knee injury followed by a shoulder injury kept him out for a prolonged period, allowing John Terry and Ricardo Carvalho to maintain their status in the starting XI.
After a season-long loan at Sevilla, he was sold off to Stuttgart.
8 Asier del Horno £8m from Athletic Club, 2005
Sometimes with transfers, it’s the hope that kills you. Del Horno was meant to be a major upgrade on Wayne Bridge. He was versatile, could play as a left-sided centre-back, or as an out-and-out left-back.
He was 24 years old when Mourinho and Chelsea signed him from Athletic Club for £8m; old enough to know the game, but young enough for Mourinho to mould into a top defender. Unfortunately, that didn’t happen.
It wasn’t all bad, though, he managed to score the only goal of his Chelsea career in a 2-0 win against Spurs at White Hart Lane. He also played a respectable amount during his one season at the club, featuring 34 times.
Sadly for Del Horno, he’s mostly remembered for his straight red card in Chelsea’s Champions League round-of-16 game against Barcelona. The defender’s tackle on Lionel Messi played a pivotal role in their elimination from the competition that year.
Valencia came calling the next summer, and Del Horno returned to Spain.
7 Radamel Falcao £4m loan from Monaco, 2015
This move was all about timing. Colombian frontman Radamel Falcao was heavily linked with Chelsea while still at Porto, but he chose Spanish side Atletico Madrid instead. He was amazing at both clubs, but injuries meant he lost a yard of pace and his confidence was shot.
He had spent the year prior on loan at Manchester United, where he also underwhelmed, scoring just four goals in 26 league appearances. If anyone could get the best out of him, it was Mourinho, right?
Wrong. Chelsea paid Monaco a massive £4m for a season-long loan. They also had a £38m option to buy, which they didn’t take up for obvious reasons. He scored just once, in a 2-1 loss against Crystal Palace.
Falcao lasted longer than Mourinho, as the manager was sacked mid-season, but he returned to the south of France that summer. He did have a bit of a renaissance, but he never again reached the heights he had at Porto and Atletico Madrid.
6 Filipe Luis £15.8m from Atletico Madrid, 2014
Filipe Luis had big boots to fill. Champions League-winning left-back Ashley Cole had just left the club for Roma, and on paper, Filipe Luis was a solid replacement. But, like so many Chelsea signings, it just didn’t work out.
He had a great time at Atletico Madrid. He was part of a stellar backline that only conceded 26 goals in 38 games, helping the Madrid side win the La Liga title for the first time in 18 years in 2014. He also played a huge role in getting his side to the Champions League final that season, a game they lost 4-1 to city rivals Real Madrid.
He didn’t get his first start until mid-September – an uneventful 1-1 draw in the Champions League against Schalke.
Come the end of the season, Mourinho confirmed that Luis would be leaving the club after just one year. He returned to Atletico Madrid for an undisclosed fee.
5 Papy Djilobodji £2.7m from Nantes, 2015
The Senegalese centre-back might have claim to the most peculiar transfer in Chelsea’s history, which is quite a statement. He joined from French side Nantes, and was omitted from Chelsea’s Champions League squad the very next day.
Perhaps the wildest statistic about his Chelsea career is that he only touched the ball during a game twice, and that was in a League Cup game against Walsall.
In the 2014/15 January transfer window, he was loaned out to Werder Bremen, where at least he played. He made 16 overall appearances for the German club, scoring twice.
Astonishingly, Chelsea managed to make a profit on Djilobodji, selling him to Sunderland for £8m in the summer of 2015.
4 Baba Rahman £14m from Augsburg, 2015
Again, it turns out that replacing Ashley Cole was pretty hard. Ghanaian left-back Rahman joined the club from Bundesliga side Augsburg for an initial fee of £14m, rising to a potential fee of £22m if certain clauses were met.
Loan after loan means that Rahman is technically the longest-serving Chelsea player on this list. Since joining in 2015, he went on a whopping seven loans to five different clubs. He only left after Chelsea terminated his contract this past summer.
During his eight years contracted to Chelsea, he only played 23 times, of which four were as a substitute. Although this mess of a deal can’t be totally blamed on Mourinho, he was the man who started it.
3 Jiri Jarosik £3m from CSKA Moscow, 2005
Now this is a throwback. Most Chelsea fans would be able to name a vast majority of the 2004/05 Premier League-winning squad, but they’d have to be a real diehard to remember Czech midfielder Jiri Jarosik.
Signed in January 2005 from CSKA Moscow for a reported £3m, Jarosik made his debut fairly quickly, but didn’t make much of an impact. He came on in the 68th minute against Scunthorpe United in the FA Cup third round.
He even started in the League Cup final against Liverpool, a game that Chelsea went on to win 3-2, but was unceremoniously replaced at half-time by Eidur Gudjohnsen.
It may be unfair to say that Jarosik was bad at Chelsea, he just didn’t really do anything, and for that reason, it’s hard to keep him out of this list. He did get a Premier League winners' medal, though, with his only full 90 minutes of the season being the game against Bolton Wanderers that secured Chelsea the league title.
Despite joining Chelsea in January, he was loaned to Birmingham City the following August. Following their relegation in 2005/06, Jarosik moved permanently to Celtic.
2 Mateja Kezman £5m from PSV, 2004
Chelsea have had a lot of disappointing strikers in their time, but Kezman might be one of the worst. The Serbian forward was unplayable at PSV, and all of Europe’s elite were circling after he scored 35 goals in 33 Eredivisie appearances.
Mourinho and Chelsea thought they had the next big thing when they signed him for £5m – they even entrusted him with the number nine shirt that had just been vacated by Jimmy Floyd Hasselbaink.
Kezman had the world at his feet, but simply couldn’t adapt to English football. It took until December for Kezman to get his first Chelsea goal, a last-minute penalty in a 4-0 home win against Newcastle.
Another player that only lasted a single season, he was sold to Atletico Madrid the next summer for £5.3m.
1 Andriy Shevchenko £30m from Milan, 2006
We have to be fair to Mourinho on this one, Shevchenko was more of a Roman Abramovich signing, but it was so catastrophic, no one else could be number one.
It’s hard to put into words just how good Shevchenko was. Before Cristiano Ronaldo and Lionel Messi came along and blew everyone away, Shevchenko had to be considered as one of the best players of the 2000s, winning the Ballon d’Or in 2004.
Chelsea have a habit of signing forwards just as they are starting to decline, and that’s exactly what happened with Shevchenko. Despite the Ukrainian’s Chelsea career never really taking off, he spent three years at Stamford Bridge.
He went back to Milan on loan in 2008/09 before re-signing for boyhood club Dynamo Kyiv on a free in August 2009.
Jose Mourinho did a lot of great things at Chelsea, but ultimately, you can’t win them all.
