1. Jose Mourinho - €1.56b
The Special One has the distinction of winning Silverware at every club he has managed so far and will be hoping to add Tottenham to that list. Jose Mourinho started his managerial career at Benfica and after a brief stint with Uniao de Leira, he caught the attention of Porto, who appointed him as the manager in January 2002. He enjoyed a lot of success in his 2 and a half year stint with the Portuguese club and made the foray into the Premier League with Chelsea next.
Mourinho spent a little over 3 seasons with the Blues and spent €371.4m on 24 players, winning 2 Premier Leagues, 2 League Cups, 1 FA Cup and 1 Community Shield. After he was sacked in September 2007, Mourinho’s next destination was Inter Milan. The Portuguese joined the Serie A side in the summer of 2008 and spent €155.8m on 13 players. He found success once again and was lured to the Bernabeu by Real Madrid in the summer of 2010.
The Portuguese stayed in Spain for 3 years, investing €186.5m on 13 players and won the La Liga, Copa Del Rey, and the Supercoppa de Espana. Mourinho then returned to the Chelsea once again for a second spell and spent another €354m on 23 players. His tenure came to an abrupt end in December 2015 and in the summer of 2016, Manchester United came calling.
Mourinho spent 2 and a half seasons with the Red Devils and was allotted €466.1m to spend on 10 players. He won one Europa League trophy and one League Cup with the Red Devils and was sacked last December. As of now, he has taken over the reins at Tottenham Hotspur this month.
The Portuguese has spent a whopping €1.56 Bn on 101 players in his managerial career and has won 33 trophies. He is the highest spending manager in world football at the moment.