14. Roland Duchatelet – Charlton Athletic
Charlton was a decent Premier League team for a number of years before crashing down into the Championship. Belgian businessman Duchatelat is the figurehead behind their descent into madness. Over the course of his five years in charge of the club, they went into severe decline.

It got so bad that they allegedly banned youth team players from drinking free bottled water at the training ground. The team suffered a second relegation to League One but the work of manager Lee Bowyer brought them back up. In the end, Duchatelet sold up in 2020.