5. Jurgen Klinsmann
Paul Marriott/EMPICS SportNow, we move on to a signing that was strange for all the right reasons. In 1994, when Spurs had finished 15th in the Premier League in the previous season and boasted a squad of players that included stalwarts like Justin Edinburgh, Dean Austin, Stuart Nethercott, Kevin Scott, David Kerslake, Darren Caskey, Jason Dozzell, David Howells, Jason Cundy and Ronny Rosenthal, Chairman Alan Sugar pulled off one of the most shocking signings in football history. World Cup winner Jurgen Klinsmann - who, being 30 years old at the time, was in his prime - signed for the club for £2 million from AS Monaco, having been wooed by Lord Sugar on one of his private yachts. The German was initially hated by the media, thanks to his part in West Germany's 1990 victory over England en route to their World Cup win and due to his tendency to dive during matches, but his performances (he scored 30 goals, won the FWA Player of the Year Award and helped Spurs finish 7th in the table), coupled with his self-deprecating humour (he would dive to celebrate his goals), was enough to endear himself to the press and he won them over. The following year, he moved back to Germany with Bayern Munich, but he would return to White Hart Lane on loan in the 1997/98 season and almost single-handedly save Spurs from relegation.