With the return of Jose Mourinho to Chelsea, many are predicting a big season for the Blues, enhanced by the fact the are likely to have a massive transfer war chest courtesy of owner Roman Abramovich.

However, Mourinho hasn't always been the most successful in the transfer market. While he made some decent signings in his first stint at Stamford Bridge - most notably Didier Drogba, Petr Cech, Michael Essien and Ashley Cole - he also made some absolute howlers and we take a look at the very worst of them.

1. Andriy Shevchenko | Bought for £30.8m, sold for undisclosed fee

At the time, the Ukrainian striker was one of the most feared and prolific goalscorers in world football.

He scored 175 goals in 296 games for AC Milan, before making a massive £30.8m summer move to Stamford Bridge in the summer of 2006, making him the most expensive transfer in British history at the time.

However, Shevchenko suffered a torrid time in the Premier League, only finding the net nine times in 48 appearances. This essentially corresponded to £1.3m per goal scored.

Although the financial loss has not been disclosed by either Chelsea or Dynamo Kiev, it is safe to assume that it at least £15-20m was lost from Abramovich's bank account.

The only positive to come from Shevchenko's signing is that it spurred Didier Drogba to 33 goals in the Ukrainians debut season, making the Ivorian the first player to do so for Chelsea since Kerry Dixon. 

2. Shaun Wright-Phillips | Bought for £21m, sold for £8.5m

After an exceptional spell at Manchester City, the diminutive winger was bought by Mourinho in 2005.

It was a difficult transition for Wright-Phillips who only managed 15 starts in his first year. This lack of matches meant that he was left out of the 2006 England World Cup squad, which devastated the young starlet.

Despite this, he always gave his all, professing his loyalty to the club when it was clear that he was low on the Stamford bridge pecking order. He made a return to his beloved Manchester City in 2008 for around £8.5m - a hefty loss of £12.5m for a player who only managed four goals in his three seasons at Stamford Bridge.

3. Asier Del Horno | Bought for £12m, sold for £7m

When he signed for Chelsea, Mourinho described the Spaniard as 'an outstanding international player'.

It just goes to show how wrong even the Special One can be. He only managed one dismal season in south London. It appears that, since his now-infamous challenge on Lionel Messi, he has never quite been the same player. He was sold by Chelsea to Valencia and replaced by Ashley Cole. 

4. Khalid Boulahrouz | Bought for £8.5m, sold for £4.25m

He only managed 13 League appearances in his two years at the club, largely due to injury and Mourinho's preference of other defenders such as Paulo Ferraira, John Terry, Ricardo Carvalho and Wayne Bridge.

This amounted to an overall payment of approximately £650k per league appearance. In 2008, he was sold to Vfb Stuttgart for half what he was bought for originally.

5. Mateja Kezman | Bought for £5.3m, sold for £5.3m

One of Chelsea’s most pointless striker signings ever, the Serbian only managed seven goals in his entire 41 game Stamford Bridge career.

Strangely enough, however, Kezman still regards his time at Chelsea as the very pinnacle of his career. Since he left the Blues, the striker has had stints at Atletico Madrid, Fenerbahçe and PSG, among others.

But what do you think, have we missed anyone off or do we have it spot on? Give your views below.

 

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Topics:
Chelsea
Andriy Shevchenko
Football
Premier League