Harry Kewell
In 2000, Harry Kewell joined the likes of Andrew Cole, Ryan Giggs and David Beckham in taking home this award. It signaled the beginning of a promising few seasons for the ex-Australia international, but it didn’t last.
As part of the Leeds United side that reached the semi-final of the UEFA Champions League towards the beginning of the noughties, he lit up not only the English top flight but also the continent’s elite competition. He was a veritable prodigy during his stay with the Peacocks and served up some quality football, but his early career showing was very much his optimum level.
A career blighted by recurring injury and confounded by disenchanting displays meant that his early-career promise was largely overshadowed by his slump after departing Leeds.
Despite winning a few titles at Liverpool, Kewell is often recalled as one of the biggest flops in the Premier League because he never quite lived up to his billing as a prospective great and spent plenty of time warming the bench.