10. Ashley Cole – Fee: £5m + William Gallas
How unlikely was this deal when it actually went down? Coming off a great season with Arsenal in 2005/06, the England fullback decided that he either wanted a big time raise or a change of scenery. Arsenal were not willing to give him the money that he desired so the man Gooners would come to call “Cashley” made a move to Chelsea FC in 2006.
After fees of £25 million were bandied about, the clubs agreed on £5 million plus defender William Gallas. The French defender had won several titles with Chelsea and at the time it looked like Arsenal were getting the better part of the deal. 10 years later, it is painfully obvious who won that particular swap.
Ashley Cole went on to win two European Cups with Chelsea, including the Champions League where he buried a crucial penalty in the final, and several other domestic trophies. Arsenal still have yet to win the Premier League since he departed and became arguably the best left-back in world football.
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