Jose Mourinho’s 15 Most Expensive Signings Ever (Ranked)

Football would certainly not be the same without the countless debates that revolve around it every day. And although most of them will never lead to any absolute truth, they have become an integral part of football-related discussions. Among the most common is the debate about whether Lionel Messi or Cristiano Ronaldo is the best player in history.

Others, such as the question of who is the best coach in history, is just as popular. And in this discussion, the name of Jose Mourinho often comes close to the top. It has to be said that the charismatic Portuguese coach has a number of arguments in his favour. It would take a long time to go through his entire list of achievements, but a quick glance at the list is all it takes to appreciate the Setubal native’s place in footballing history.

A legend largely written with the help of the many talented players he had under his command, sometimes brought to him through extremely expensive transfers. This article now lists the 15 most expensive signed by Mourinho, ranging from his managerial stints at Manchester United, Chelsea and AS Roma among others. Will the new Benfica boss be adding to this list at his new job?

15

Willian

Transfer fee: £30m (From Anzhi to Chelsea)

Credit: Photo courtesy of Reuters.

One of the most talked-about transfers of the Premier League era, Willian was of course all set to join Tottenham before he quite literally turned around and signed for London rivals Chelsea instead. It was a coup of the highest order, and Willian would prove his worth by constantly being a thorn for numerous Spurs teams over the years.

As well as his record in those London derbies, Willian would help win multiple titles at Chelsea, and so Blues fans have a lot to thank Jose Mourinho for in terms of bringing him in the first place.

14

Luka Modric

Transfer fee: £30m (From Tottenham to Real Madrid)

One of the greatest midfielders in football history, Luka Modric became a Real Madrid icon following his move from Tottenham. The Croatia international orchestrated things for Los Blancos for multiple years at the Santiago Bernabeu, and became a multiple-time Champions League winner at the club.

While Mourinho perhaps didn’t get to see the full fruits of his signing – Modric arguably enjoyed his best years under both Zinedine Zidane and Carlo Ancelotti – he more than delivered on the move.

13

Cesc Fabregas

Transfer fee: £30m (From Barcelona to Chelsea)

One of the key signings of Jose Mourinho’s second runs as Chelsea manager, Cesc Fabregas announced himself onto the stage as a Blues player with one of the finest assists the Premier League has ever seen when he set up Andre Schurrle with an iconic first-time pass against Burnley at Turf Moor.

Fabregas may have been an Arsenal hero, but Mourinho opted to bring the star to Stamford Bridge, and he more than repaid his manager’s faith with a series of scintillating performances in the middle of the park.

12

Victor Lindelof

Transfer fee: £31m (From Benfica to Manchester United)

As Mourinho looked to reshape Manchester United’s defence, he decided to bring in Sweden international Victor Lindelof from Portuguese side Benfica. The centre-back was a stand-out performer for the Liga NOS outfit, but never really blossomed into the kind of defender his early potential had shown.

United reportedly forked out a fee in the region of £31m to bring him in, but Mourinho never truly got the best out of Lindelof, and it’s fair to say his Old Trafford career never panned out the way he would have wanted.

11

Eric Bailly

Transfer fee: £45m (From Villarreal to Manchester United)

In the summer of 2016, Eric Bailly left Villarreal to join Manchester United, having finished fourth in La Liga and reached the semi-finals of the Europa League. At the age of 22, the centre-back became the first signing of the Mourinho era, when he was made official as the Red Devils’ new coach a few weeks earlier.

A player with a bright future, his English adventure soon took an unfortunate turn. After an encouraging first season, punctuated by a European League title, the Ivorian saw his destiny turned upside down by a host of physical problems, more or less serious, which gradually pushed him further and further away from a starting berth. In two and a half seasons under the Portuguese manager, Bailly missed 38 games through injury.

10

Diego Costa

Transfer fee: £45m (From Atletico Madrid to Chelsea)

Diego Costa is one of those players who is better to have with you than against you. He is a enigmatic character and, unsurprisingly, one of Mourinho’s greatest successes. Having returned to Chelsea the previous season, the Portuguese was keen to renew his attacking line-up for the 2014 summer transfer window.

And it was the Spanish striker who was the Lusitanian coach’s choice. Fresh from a season in which he won La Liga and finished third top scorer (27 goals in 35 games) for Atletico Madrid, the 25-year-old centre-forward signed for the London club for a cheque of €38m. It proved to be an immediately fruitful marriage, with Costa scoring 20 goals in 26 Premier League games to help the Blues to their fifth league title in their history.

9

Michael Essien

Transfer fee: £45m (From Olympique Lyonnais to Chelsea)

The relationship forged by Mourinho and Michael Essien is, by their own admission, similar to that between father and son. In 2005, the defensive midfielder, who had just won a second consecutive French league title with Olympique Lyonnais, moved to Chelsea after weeks of negotiations.

It was a record transfer for the West London club, and one that quickly paid for itself. The Ghanaian was immediately introduced as an undisputed first-team regular, and during his seven-and-a-half seasons with the Blues, he helped the club win numerous titles. He won the Champions League in 2012, two league titles (2006, 2010) and three FA Cups (2007, 2009, 2012), before leaving England for Italy, where he joined AC Milan in January 2014.

8

Didier Drogba

Transfer fee: £45.5m (From Olympique de Marseille to Chelsea)

When Didier Drogba arrived at Chelsea in the summer of 2004, many still had no idea who he was. While it is true that the Ivorian striker was coming off a great season with French giants Olympique de Marseille, with whom he was decisive 39 times (32 goals, seven assists) in 55 games, his lack of experience at the very highest level had some observers wondering. Mourinho, on the other hand, was already aware of the Abidjan native’s potential.

So much so, in fact, that he asked Roman Abramovich to invest with his eyes closed and let time take its toll. What followed was clearly in the Portuguese’s favour. In the space of eight seasons, Drogba rose to the rank of club legend, punctuating his adventure with a goal and the decisive penalty against Bayern Munich to give Chelsea their first Champions League. A player whose praises continue to be sung at Stamford Bridge and in Marseille, where his only season in France is now deified.

7

Tammy Abraham

Transfer fee: £48.5m (From Chelsea to AS Roma)

A confident player is one whose chances of success are maximised. Tammy Abraham can testify to this. Considered more of a second-rate player than a real starter at Chelsea, the English striker, who was much coveted by Mourinho, who had recently become coach of AS Roma, decided to leave his parent club in the summer of 2021.

It’s a decision that paid off for the centre-forward, whose first season was crowned with success. He scored 17 goals in Serie A and nine in the UEFA Europa Conference League to help his side lift the newly-created European Cup trophy. It was the high point of a brilliant season, but the Englishman was unable to repeat the feat the following year. Less decisive, he suffered a serious cruciate ligament rupture in June 2023. This setback kept him out of action for almost a season.

6

Henrikh Mkhitaryan

Transfer fee: £49.7m (From Borussia Dortmund to Manchester United)

Having bagged 15 assists for Borussia Dortmund and been named Bundesliga Players’ Player of the Season at the end of the 2015/16 season, Henrikh Mkhitaryan joined Manchester United the following summer. A free transfer for the player who then became the first Armenian in Premier League history.

But while expectations were high, it was difficult to assess his 18 months at Old Trafford. While he proved invaluable in winning the 2017 Europa League, his performances in the Premier League were mixed. To the point where Mourinho all but dismissed him the following winter. An unbearable situation for the player, who saw the arrival of Alexis Sanchez at the Red Devils in January 2018 facilitate his departure to Arsenal.