#3 Carlo Ancelotti | €1.37 billion

The current Real Madrid coach is one of the greatest and most successful managers of the 21st century, with 20 titles to his name.
Carlo Ancelotti has managed some of Europe's best clubs including AC Milan, Juventus, Chelsea, PSG, Real Madrid and Bayern Munich. The 62-year-old began his managerial career as the assistant manager of the Italian national team in 1992. The Italian has managed eight of the biggest clubs in European football in the 21st century and is one of three managers to have won the prestigious UEFA Champions League thrice. Ancelotti won Europe's premier club competition twice with AC Milan and once with Real Madrid in the 2013-14 season.
Ancelotti has been at the helm of some of the wealthiest clubs in world football and it's no surprise that he's spent well over a billion euros. The Italian has signed 88 players since 2000 for a combined cost of €1.37 billion.
#2 Pep Guardiola | €1.59 billion

Pep Guardiola has built a reputation of being one of the highest spenders among his peers and finds himself in second place on our list.
While many football fans would've expected to see Guardiola at the top of this list, he's spent €17 million less than our first-placed candidate. However, the Spaniard has the highest spend on average, as he has splurged €1.59 billion on just 67 names. Some of Guardiola's most expensive signings include Jack Grealish at €117.50m, Ruben Dias for €68m and Zlatan Ibrahimovic for €69.50m on a player-plus-cash deal.
The Spaniard has almost breached the £1billion mark since taking over the reins at Manchester City in 2016. Guardiola is the most successful manager of the 21st century, with 31 titles to his name since 2000s.
#1 Jose Mourinho | €1.76 billion

Jose Mourinho is first on our list with an eye-watering spend of €1.76 billion on player recruitment since the turn of the century.
The self-proclaimed Special One has signed more players than anyone on the list and has snapped up over a 100 players in his career. Mourinho has splurged a total of €1.76 billion on 104 players across nine different clubs since 2000. His most expensive signings include Paul Pogba for £94.5 million, Romelu Lukaku for £76.2 million and Fred at £53.1 million. Five of his six most expensive transfers came during his tenure as Manchester United manager.
The Portuguese tactician has won a whopping 25 trophies in the 21st century. Mourinho has managed some of the biggest clubs in world football, including Benfica, Porto, Chelsea, Inter Milan, Real Madrid and Manchester United. He will always be remembered for leading the underdogs, Porto, to the 2003-04 Champions League title.