2nd – Roger Johnson
The most bizarre and unwanted transfer in West Ham’s recent history was that of Roger Johnson. Picture the scene, your side is battling against the dreaded drop and you need some inspiration to spur your side on – a leader if you will. So who do the Hammers go and sign? Mr Relegation himself. Johnson, at the time of signing, had been part of a relegated side for three successive seasons and showed exactly how appalling he was with his defensive display during the 6-0 defeat to Manchester City in the League Cup semi-finals. It may not be a transfer that cost the Hammers dearly in terms of wages or transfer fee, but it was certainly one that made you shout expletives from your armchair and lose all hope of remaining a Premier League team. West Ham survived the 2013-2014 season by some wondrous miracle, probably due to Johnson being restricted to four appearances.