Mourinho, Simeone & Co – Managers who have spent the most money on transfers of all-time

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12 managers spent €1b+ 

The money being spent in football has got more and more out of control throughout the years. Clubs continue to spend €100’s of millions each season in an attempt to build the best squads possible to compete at the top level. But which managers have splashed out the most money on transfers in the history of the game? Of course, in a modern football club structure, the manager alone is not solely responsible for incomings and outgoing, but they are still sure to benefit from their club spending big money. Here at Transfermarkt, we have compiled a list of the bosses to spend the most cash, with some of the best names to sit in the dugout in the past few decades featuring.

Leading the way is the winning machine Pep Guardiola. Across his time at Barcelona, Bayern Munich and Manchester City, the Spaniard has spent a mouth-watering €2.06b on players. In that time he has won a sensational 39 trophies, which goes to show a lot of the money spent has been well spent. His record signing was Jack Grealish, who was signed by Man City from Aston Villa in 2021 for €117.5m. Nine of his top 10 transfers have come as boss of the Sky Blues, with Zlatan Ibrahimović the only exception – he was signed by Barcelona for €69.5m back in 2009. 

In second place is ‘the special one’ José Mourinho. The Portuguese tactician, who has won 26 trophies, has spent €1.91b on transfers in his managerial career. The most expensive of which was Paul Pogba, who Mourinho’s Man United paid €105m for from Juventus in 2016. The legendary Carlo Ancelotti takes third – the current Real Madrid boss has total expenditure of €1.79b spent throughout his long and successful career, in which he has won 29 trophies. He’s followed by another Italian in fourth, with Massimiliano Allegri spending €1.42b throughout his career.

In fifth is Atlético Madrid manager Diego Simeone, who has also spent €1.42b during his managerial career. Sixth goes to Antonio Conte, with the Italian having spent €1.33b – he has won just eight career trophies despite that spend. In seventh is Chilean coach Manuel Pellegrini with a total spend of €1.25b. Eighth is German Thomas Tuchel who also has a career spend on transfers of €1.25b. Current Aston Villa boss Unai Emery takes ninth with a spend of €1.23b, with Argentine Mauricio Pochettino completing the top 10 with a spend of €1.15b – he is the only manager in the top 10 to win less than five trophies, with just three in his career to date.