Jose Mourinho is still the biggest spender on transfers

Inflation in the world of football causes more expensive signings year after year. Therefore, it is not surprising that the coaches which have spent the most money on signings in history are current coaches or at least ones in the last two decades.
Jose Mourinho leads the way with 1.56 billion euros spent on 97 footballers. Mou started spending in Portugal, but he started to become a big spender in his first spell at Chelsea.
At Inter Milan and Real Madrid he continued to spend, but he secured top spot in the ranking when he returned to England. At Chelsea he invested again without caring about the cost and above all, at Manchester United he did the same at a club which needed mass changes.
Behind him is Carlo Ancelotti. The Italian managed, among others, AC Milan, Juventus and Real Madrid and is now hardly cutting back at Napoli. He has signed 85 players and spent 1.23 billion euros.
In third position is Pep Guardiola. Despite the fact he started his managerial career after Mourinho and Ancelotti, the Man City manager is on the way to the top. He has spent 1.15 billion euros for just 52 footballers. He could move into second once this summer's window is out.
Manuel Pellegrini is behind him. He had spells at big spending clubs like Real Madrid and Manchester City. He also had the odd year of major spending at Malaga and Villarreal. The West Ham managrt has currently forked out 1.04 billion for 82 players.
Making up the top 5 is Massimiliano Allegri. He has just coached three clubs, two of them big, but he has had free reign to spend what he wants. In his time at Juventus and AC Milan, the Italian coach invested 1.02 billion euros and signed 87 people including Cristiano Ronaldo.
Not even being at Juventus, a club who is great at signing players on the cheap, has prevented him from making this list. Wenger, Ranieri, Mancini, Benitez and Emery are the rest in the top 10.