Chelsea’s nine strangest transfers, and the rumoured move that would eclipse the lot

Reports in the Daily Express on Friday claimed that Chelsea are preparing a shock move for Tottenham Hotspur striker Emmanuel Adebayor, as Jose Mourinho searches for an experienced forward to replace Didier Drogba.

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Mourinho worked with the Togo international during his time at Real Madrid, and by all accounts the pair have a good relationship. However, it would come as a huge surprise if he were indeed to move for an ex-Arsenal and Tottenham player, who’s scored just twice this term.

Of course, there have been plenty of strange signings at Stamford Bridge throughout the Roman Abramovich era. In the list below, we list the worst nine offenders, a list that Adebayor will desperately be trying to avoid, should he ever make the surprise switch!

9) Jose Bosingwa (July 2008, £16.3m)

The Portuguese made 125 appearances for Chelsea, but never truly lived up to his impressive price tag, as Branislav Ivanovic eventually became the Blues recognised right-back. Frustratingly lazy and consistently casual, he eventually left for Queens Park Rangers.

8) Asier Del Horno (June 2005, £8m)

Another low-quality full-back, who was left out in the cold following Ashley Cole’s arrival from Arsenal. He made 34 appearances during his only season at the club, and was quickly on the way out after the England international became available.

7) Alexei Smertin (August 2003, £3.45m)

Lacked the quality to play regularly in a Chelsea side that was rapidly changing as the Russian financed their heavy spending. He found himself loaned out to Portsmouth, where he was plunged into a relegation scrap, and never really recovered.

6) Khalid Boulahrouz (August 2006, £6m)

The Dutchman was once described as the perfect cover for all Chelsea’s defensive options, but he never lived up to his billing. Chelsea’s defence was consistent and was rarely altered, while injuries further restricted his opportunities to play in the first-team.

5) Mateja Kezman (July 2004, £5.3m)

Managed just seven goals in 40 games for the club, departing after his one and only season. He struck 129 goals in 176 games for former club PSV Eindhoven, but was never able to live up to that reputation in a blue shirt, although he did manage a goal in the Carling Cup final.

4) Yuri Zhirkov (July 2009, £18m)

Zhirkov became the most expensive Russian player of all time when he joined the Blues. He made just 29 appearances in two years at the club as he struggled with injuries, while Ashley Cole and Florent Malouda dominated the left-hand side.

3) Juan Sebastian Veron (July 2003, £15m)

The Argentine had already flopped at Old Trafford with Manchester United, so it came as a surprise when Chelsea decided that he was worth taking a risk on. He made just 15 appearances, and spent the last three years of his contract playing out on loan before leaving for nothing.

2) Andriy Shevchenko (May 2006, £30m)

The Ukrainian was believed to be close friends with Abramovich when he joined the club, and that’s the only reason we can think that this move ever happened. The former AC Milan great was already at the end of his peak years, and he never came good for the Blues.

1) Adrian Mutu (July 2003, £15.8m)

Mutu managed just 36 appearances and ten goals for the club, after which he was found guilty of taking cocaine and was sacked. He also endured a series of heated arguments with new manager Jose Mourinho, who never appeared to be keen on the forward.