Gianluca Nani arrived as West Ham's first - and only - technical director, and left Upton Park having played a significant role in almost condemning the east London club into administration.
The Italian was responsible for the recruitment of a number of high-profile players on exorbitant salaries, and also broke the club's transfer record with the signing of Savio Nsereko from Brescia - his former club.
Have you heard of Savio? Probably not. The German played just 10 games for the Hammers before being farmed back to Italy and, in the four years since his departure, has featured for no less than eight teams.
Nani's behaviour - along with other members of the club's hierarchy - also resulted in the resignation of Alan Curbishley, who became apoplectic after Anton Ferdinand and George McCartney were sold against his wishes.