Carlo Ancelotti has been a manager for 30 years. The Italian tactician has managed some of the biggest clubs in the world and coached some of the most iconic stars in football history. As a coach, he has overseen nearly 200 signings, worth over £1.5bn spent in the transfer market. Jude Bellingham (€127m/£106m) is the most expensive player ever recruited under his stewardship. While that transfer has been a success, the same cannot be said for many others.
10. Rivaldo
In the summer of 2002, Rivaldo joined AC Milan on a free transfer from Barcelona. Despite being 30 years old, the Brazilian forward had just enjoyed a strong World Cup, scoring five goals. He arrived as an international star to be managed by a promising coach. Ultimately, the Ballon d'Or winner would score just eight goals in 40 matches for the Rossoneri.
9. Ronaldo (€7.5m/£6.3m)
To replace Andriy Shevchenko, who incidentally became one of Jose Mourinho's great flops, AC Milan attempted to revive Ronaldo in 2007. An audacious gamble led by Carlo Ancelotti, it ended in bitter failure as the maverick Brazilian striker suffered another serious knee injury, bringing an end to his adventure in European football.
8. Ricardo Oliveira (€15m/£12.5m)
Before R9, Milan and Carlo Ancelotti tried their luck with another Brazilian player, Ricardo Oliveira. Signed for €15m (£12.5m) from Real Betis, the forward struggled for goals in Lombardy, managing just five strikes in 37 appearances.
7. Lucas Silva (€15m/£12.5m)
After bringing La Decima to Madrid, the Mister wanted to find Brazilian football's next star. In a highly competitive midfield, Lucas Silva failed to establish himself. The pressure of an anticipated transfer to the Merengues was certainly too much for Lucas Silva to bear.
6. Yuri Zhirkov (€21m/£17.5m)
Arriving from CSKA Moscow, Yuri Zhirkov had impressed at Euro 2008. But at Chelsea, the step up was undoubtedly too great, and despite his good intentions, the left midfielder failed to convince Carlo Ancelotti.
5. Allan (€25m/£21m)
While he was coveted by PSG and other major European clubs, Allan followed Carlo Ancelotti to Everton. The two men had worked well together at Napoli, but the partnership would not prove fruitful in the Premier League. The Brazilian midfielder struggled immensely to impose himself at the Toffees.
4. Asier Illarramendi (€32m/£27m)
The Spanish midfielder was one of Carlo Ancelotti's first signings at Real Madrid. Often criticised by the Madrid press, Asier Illarramendi proved to be a major flop and left the club after two forgettable seasons.
3. Renato Sanches (€35m/£29m)
Winner of Euro 2016 and awarded the Golden Boy title, the Portuguese midfielder arrived at Bayern Munich under enormous pressure. However, his performances were deemed insufficient and he failed to earn the trust of the Italian coach.
2. Hirving Lozano (€50m/£42m)
Even today, Hirving Lozano remains Napoli's second-most expensive transfer in history. While the Mexican winger's spell was not catastrophic, Neapolitan fans expected much more. The association between Hirving Lozano and Carlo Ancelotti lasted only a few months and was far from promising, despite the transfer fee.
1. Fernando Torres (€58m/£50m)
The fifth-most expensive transfer in Carlo Ancelotti's career and the first outside Real Madrid players. After shining at Liverpool, El Nino succumbed to Chelsea's charms. It took just six months for Blues fans to realise this transfer was a resounding flop. El Mister could do nothing about it – Fernando Torres would be a shadow of himself at Stamford Bridge, despite a few flashes of brilliance after Carlo Ancelotti's departure. One of the great regrets of his managerial career.
This article was originally published on Top Mercato.