When you have had a manager like Harry Redknapp at the helm of your football club, there’s always going to be a significant amount of transfer activity at your club. Sure enough, ‘Arry did plenty of ‘wheeling and dealing’ during his years at White Hart Lane, but in all honesty, many of Spurs’s transfer disasters came long before he and the current man at the top, Andre Villas-Boas, arrived at the club.
After a decade of mediocrity in the 90’s that saw some dreadful players pull on the white shirt, Spurs decided to splash the cash under Chairman Daniel Levy. It’s fair to say some purchases were better than others and the likes of Robbie Keane, Jermain Defoe and Michael Dawson can be viewed as money well spent. However, the Spurs reserve side has featured many an expensive player in recent years who simply couldn’t cut the mustard in the first team. See if you agree if our worst Tottenham signings XI from the Premier League era.