Manchester United manager Jose Mourinho and Manchester United's Paul Pogba celebrate after winning the UEFA Europa League Final in Stockholm

Jose Mourinho’s most expensive signing at every club – & how they fared

No manager in the history of football boasts a higher transfer expenditure than Jose Mourinho. Over the course of his managerial career, his signings tally almost €2billion. 

Having managed the likes of Chelsea, Inter, Manchester United and Real Madrid, the Portuguese coach has been backed with a number of big-name superstar signings – some of which have lived up to their billing, some of which haven’t.

We’ve taken a look at the most expensive signing from each of Mourinho’s managerial stints. Note: we’ve not included Benfica, where he didn’t make any signings, or Uniao de Leiria, where he only made a small number of inexpensive signings.

Porto – Benni McCarthy

Mourinho spent two years at the Estadio do Dragao, won back-to-back league titles, a UEFA Cup and the Champions League – and his record signing in that time was Benni McCarthy from Celta Vigo at just €3.5million.

The South African forward just edged out a young Nuno Espirito Santo as Mourinho’s top signing at Porto. He was eventually sold on to Blackburn Rovers for a small profit, while other high-profile departures that made their name under Mourinho – Ricardo Carvalho, Deco, Paulo Ferreira – made the Portuguese giants a small fortune.

Chelsea – Andriy Shevchenko

Mourinho’s first stint at Stamford Bridge was largely defined by a number of successful big-money signings.

Roman Abramovich was splashing the cash and the likes of Didier Drogba, Michael Essien, Arjen Robben and Petr Cech proved well worth the money.

But Mourinho’s biggest buy failed to live up to the billing. Andriy Shevchenko had established himself as one of the finest strikers of his generation at Dynamo Kyiv and AC Milan – he had both a Champions League and Ballon d’Or under his belt by the time he arrived at Stamford Bridge in the summer of 2006.

The Ukrainian signed for a club-record £30million but struggled to adapt to English football. He scored just 15 goals in 53 appearances under Mourinho and eventually moved on at a considerable loss.

READ: Remembering when Shevchenko caused Roman and Jose to break up

Inter – Diego Milito

Now we’re talking.

Portuguese compatriot Ricardo Quaresma was Mourinho’s big-money signing in year one, but the mercurial winger struggled at the San Siro and was voted the worst player in Serie A in his debut season.

But Diego Milito, who beat that when he signed from Genoa for €28million in 2009, proved to be an inspired signing. The addition that fired Inter to the treble, Milito scored 30 goals in his debut season, including clutch strikes in the title run-in, the Coppa Italia and Champions League final.

Worth it just for that.

Real Madrid – Luka Modric

Florentino Perez declared Mourinho as “this year’s Galactico” when he arrived at the Bernabeu in 2010. And Real Madrid’s really extravagant signings – Cristiano Ronaldo, Kaka, Gareth Bale, James Rodriguez – came before and after the manager’s three-year reign in the Spanish capital.

Madrid’s record signing during Mourinho’s tenure was Modric at a relatively modest €35million. The pair only spent a year together at the Bernabeu and it proved one to forget as Los Blancos went trophyless and Modric was voted by Marca among La Liga’s worst signings.

But the Croatian turned out alright in the end, didn’t he?

READ: Remembering when Luka Modric was voted La Liga’s worst signing

Chelsea – Diego Costa

Shevchenko remains Mourinho’s most expensive signing at Chelsea, but we’ve included the top buy from his second stint too.

This one was much more successful. Costa’s snarly attitude meant he arrived at Stamford Bridge entirely unbothered by their strike curse and delivered.

The Spain international’s 20 Premier League goals fired Chelsea to the 2014-15 title, Mourinho’s last, and once again delivered with another 20 goals in the 2016-17 title won under Antonio Conte.

Manchester United – Paul Pogba

Mourinho’s most expensive signing period, Pogba is the coach’s only €100million+ signing and – to be frank – among his very most disappointing.

It wasn’t all bad. The midfielder looked a bright spark as United won the League Cup and Europa League in their first season together at Old Trafford, but both player and coach went on to sour their legacies in Manchester.

And to say they didn’t get on would be underselling it.

“Once I had a great relationship with Mourinho, everybody saw that, and the next day you don’t know what happened. That’s the strange thing I had with Mourinho and I cannot explain to you because even I don’t know,” Pogba recalled back in 2021.

“I would like to say that I couldn’t care less with what he says. I am not interested at all,” Mourinho responded. Ouch.

Tottenham – Giovani Lo Celso

Lo Celso at Tottenham. Mourinho at Tottenham. That whole weird lockdown period. None of it feels like it really happened, does it?

But it did. Spurs bought Lo Celso for a club-record £55million(!) back in 2019. Shrug.

Roma – Tammy Abraham

Maybe it’s just us, but we find it impossible not to hear Abraham’s voice not in Mourinho’s distinctive Portuguese accent, with an added H – Tammy Habraham.

Uh, anyway, the Cobham academy graduate never featured for Chelsea under Mourinho but the pair have since teamed up at Roma.

He’s got a reasonably decent record for the Italian club – 36 goals and 12 assists in 107 appearances – but hasn’t done quite enough to move beyond the fringes of Gareth Southgate’s England squads.

You imagine he’ll move back to the Premier League sooner or later. Watch this space.

READ NEXT: Ranking Jose Mourinho’s 11 signings for Man Utd from worst to best

TRY A QUIZ: Can you name Mourinho’s 35 most-used players throughout his career?