27. Fernando Torres
Torres became a Liverpool icon because of his incredible scoring record for the team. However, things went downhill for the Spaniard as he suffered injuries. Then he lost faith in the team and threatened to leave his team high and dry in 2011.
Chelsea signed Torres for a then-record British fee of over $55 million. This left Liverpool in a state of panic because they lacked a star forward. Then they infamously splurged millions on Andy Carroll, who became one of their worst signings ever. But they also bought the brilliant Luis Suarez (via The Guardian).