Jonathan Woodgate may seem like a strange inclusion on this list, as he has undoubtedly proven himself to be a great player during his career and he was part of Tottenham's League Cup winning side of 2008, but the fact is he's been stealing a living from football for most of his professional life. Woodgate is injury-prone incarnate and spends most of his time in the treatment room and unable to play. He cost Spurs £8 million when he arrived from his hometown club, Middlesbrough, and he spent three and a half years at White Hart Lane. In that time, he played just 49 Premier League games and just 65 games in total. He also went off injured in those games more times than anyone would care to count. Had he and Ledley King been injury-free in their time together at Spurs, they could have been one of the best defensive partnerships in the world - literally. However, given that they were both injured so often, it really was a massive shame. Still, at least King didn't cost Spurs anything, managed to play more than 300 games for the club, and offers them so much more in terms of his leadership, coaching and ambassadorial roles.
