#2 Leeds United
Leeds United did so well at going from one of the best clubs in Europe to has-beens, in such a short period of time, that they have their own phrase called ‘doing a Leeds’. The phrase can be used for any situation where one has enormous riches, but in pursuit of more, one ends up losing everything.
Leeds were one of the dominant teams of England in the late nineties. They won the last First Division title before it was re-christened as the Premier League. Managing to string together a consistent run of top four finishes, Leeds were always there and thereabouts in the Premier League title race. Over this period, they also started building one of the most formidable teams of the Premier League era.
The likes of Jonathan Woodgate, Rio Ferdinand, Mark Viduka, Harry Kewell and Dominic Matteo were stalwarts in a thriving side. Leeds’ dream culminated in a semi-final appearance in the 2001 Champions League. The club felt there was a need to step up a level and spent extravagantly on players, hoping a consistent influx of revenue from the Champions League and Premier League bonuses would help them overcome initial losses.
In the 2002/03 season, Leeds failed to qualify for the Champions’ League and that tipped them over the edge of the debt precipice. Riddled with a debt of £119 million, they could no longer sustain player wages due to debt repayments. Things reached an all new low when the club voluntarily entered administration before the penultimate game of the 2006/07 season, and incurred a 10 point penalty which got them relegated to League One.