4. Jose Bosingwa
Not necessarily one of Chelsea’s worst ever players, it is more the large transfer fee mixed with the lack of impact made at Stamford bridge which condemns him to a place on the list. In 2008 Bosingwa was signed from Porto for a rather large fee of £16.2 million. The former Portugal international made 89 Premier League appearances over 4 years, scoring 3 goals in the process. Now at Turkish side Trabzonspor, the former Boavista man will be left wondering what could have been.