Football: Top 15 worst signings of Jose Mourinho (With Pictures)

14. Steve Sidwell 

One may consider leaving Steve Sidwell off of this list entirely because he joined Mourinho and Chelsea via a free transfer in the summer of 2007. The reason that Sidwell makes the cut is because it did not take long for everybody, Mourinho included, to see that Sidwell was not good enough to earn minutes for Chelsea. Acquiring Sidwell was not a complete bust for Mourinho and for Chelsea, as the club did receive an undisclosed transfer fee when the player was sold to Aston Villa. After leaving Chelsea, Sidwell was little more than a middle-of-the-road player.