Jose Mourinho: The 10 best and 10 worst signings of his career | OneFootball

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Jose Mourinho is unquestionably one of the greatest managers of all time. While his reputation as a truly elite coach may have dwindled a little in recent years, the Portuguese tactician remains one of the most respected figures in the game at the age of 60.

Mourinho cemented his reputation as one of the world’s most exciting young coaches when he won the Champions League with FC Porto in 2004. He went on to manage some of Europe’s biggest clubs including Chelsea, Inter Milan, Real Madrid, Manchester United, and Tottenham.

Employed by AS Roma since 2021, we thought we’d take a closer look at the 10 best signings of Mourinho’s illustrious managerial career. And, for the purposes of balance, we’ll also analyse his 10 worst signings from his 20+ year career. Even the best managers sometimes get it very badly wrong in the transfer market…

Mourinho’s best signings

10. Luka Modric (Tottenham to Real Madrid | 2012 | £30m)

When Mourinho signed Luka Modric from Tottenham in 2012, little did he know that he’d be managing Spurs himself seven years later. Modric initially struggled at the Bernabeu - he was even named La Liga’s worst signing for 2012, months after his arrival - before finding his feet and silencing all of his critics in spectacular fashion.

The Croatian, who won the 2018 Ballon d’Or, didn’t produce his best form under Mourinho - but the Portuguese coach still deserves credit for bringing the world-class midfielder to the Spanish capital in the first place. Modric will be remembered as one of Real Madrid's greatest ever players and one of the best midfielders of any generation.

9. Zlatan Ibrahimovic (PSG to Man Utd | 2016 | Free)

Without Mourinho, Manchester United would not have signed Zlatan Ibrahimovic in the summer of 2016. It was because the two men already had an excellent relationship that Zlatan moved to Old Trafford as a free agent after leaving Paris Saint-Germain.

The mercurial Swedish forward turned on the style during his first season at Old Trafford, scoring 28 goals in 46 appearances and winning the League Cup and Europa League in the process. He also netted the winning goal in the Community Shield. If only he’d joined United a few years earlier, eh?

8. Ricardo Carvalho (Porto to Chelsea | 2004 | £20m)

Mourinho knew Ricardo Carvalho was tailor-made for the Premier League after managing the Portuguese defender during his spell at Porto. Chelsea splashed out £20 million for Carvalho, who went on to play 210 games for the west London outfit.

The Portugal international left Stamford Bridge in 2010, reuniting with Mourinho again at Real Madrid, and won a host of titles during his time with the Blues, including three Premier Leagues. He ended his career in 2017 following a brief spell with Shanghai SIPG in China.

7. Benni McCarthy (Celta Vigo to Porto | 2003 | £3.15m)

Benni McCarthy had already spent time at Porto and made a positive impact - on loan from Celta Vigo during the 2001-02 campaign - before Mourinho brought the South African striker to the Estádio do Dragão permanently in 2003.

McCarthy went on to score 25 goals in 47 games during his debut campaign with Porto who, of course, won the Champions League that season. Not bad for three million quid. Working under Mourinho served him well for his post-playing career. He's currently employed by Man Utd as one of Erik ten Hag's first-team coaches.

6. Diego Milito (Genoa to Inter Milan | 2009 | £22.2m)

The 2009-10 season was Diego Milito’s first campaign at the San Siro - and what an impact the Argentine striker made. He scored 30 goals in 52 appearances, including both goals in the 2010 Champions League final against Bayern Munich, earning himself the Man of the Match award in the process.

Milito went on to score 75 goals for Inter before leaving the club - and European football - in 2014. The South American will forever occupy a special place in Mourinho's heart thanks to that legendary Champions League final performance in Madrid.

5. Wesley Sneijder (Real Madrid to Inter | 2009 | £13.3m)

Inter Milan won the treble in 2010 and Wesley Sneijder, also in his debut season with the Nerazzurri, was outstanding. The Dutch playmaker flourished under Mourinho and took his excellent club form into the 2010 World Cup, where he finished as a finalist with the Netherlands and won the Silver Ball.

He was unfortunate to miss out on a place inside the Ballon d’Or top three that year. Barcelona trio Lionel Messi, Andres Iniesta and Xavi all made the podium at Sneijder’s expense.

4. Diego Costa (Atletico Madrid to Chelsea | 2014 | £32m)

Diego Costa had already established his status as one of Europe’s best strikers with Atletico Madrid when Mourinho brought the aggressive forward to Stamford Bridge in 2014. The Brazil-born Spain international further enhanced his reputation as a top striker with Chelsea, scoring 21 goals in his first season with the Blues and winning both the Premier League and League Cup in the process.

He won another Premier League winners’ medal with the Blues under Antonio Conte in 2017 before falling out with the Italian coach and re-joining Atleti. The 34-year-old is now back in his native Brazil with Botafogo.

3. Samuel Eto’o (Barcelona to Inter | 2009 | (Barcelona paid £40 million + Eto’o for Zlatan Ibrahimovic)

Mourinho didn’t want to lose Zlatan Ibrahimovic to Barcelona, but what a stunning deal Inter got in return. As well as securing the services of the brilliant Samuel Eto’o, they also banked a whopping £40 million.

Eto’o went on to win the treble in his first season at Inter, where he scored 16 goals in 48 games. The Cameroon international then bagged 37 goals in 53 games the following season, although Mourinho was managing Real Madrid by this point. Mourinho linked up with Eto’o again in 2013 at Chelsea.

2. Ashley Cole (Arsenal to Chelsea | 2006 | £5m + William Gallas)

Ashley Cole is arguably the best left-back of the Premier League era, and Chelsea landed the England international from Arsenal for a bargain £5 million plus William Gallas. Cole was present for the end of Mourinho’s first spell at Stamford Bridge, as well as the beginning of his second stint.

After hanging up his boots in 2019, following a brief spell with Derby County, Cole began his coaching career. The 42-year-old has worked in a coaching capacity with Derby, Chelsea's academy, England's Under-21s, and Everton.

1. Didier Drogba (Marseille to Chelsea | 2004 | £24 million)

One of the biggest legends in Chelsea’s history, Mourinho was the man responsible for bringing Didier Drogba to west London from Marseille in 2004. The Ivorian striker went on to score 157 goals in 341 games for the club, winning a host of major honours, including four Premier Leagues, the same numbers of FA Cups and, of course, the Champions League.

Speaking on beiN Sports in 2019, Mourinho said: “He had already played for Guingamp, Marseille, Le Mans, so when I took him to Chelsea I remember clearly [Chelsea's then owner Roman] Abramovich was asking me, ‘Who? Who do you want as a striker?’

“With all the big names in Europe at that time I said Drogba. ‘Who is he? Where’s he playing?’ (I said) 'Mr Abramovich – pay. pay, and don’t speak'. And Didier was an iconic player for Chelsea, for the Premier League."

Mourinho’s worst signings

10. Fabio Coentrao (Benfica to Real Madrid | 2011 | £27m)

It’s not as if Mourinho signed a bad player in Fabio Coentrao - the Portuguese left-back looked outstanding at Benfica - but there’s no doubt this turned out to be a disappointing transfer. Coentrao was signed to provide Marcelo with additional competition at left-back, but the Brazil international continued to get better and better, leaving the Portugal international in his shadow.

He spent time on loan at AS Monaco and Sporting Lisbon before leaving the Bernabeu for Rio Ave in 2018. The defender retired in 2021 and unexpectedly decided to become a fisherman. One of the more unusual post-football career jobs, that one.

9. Baba Rahman (Augsburg to Chelsea | 2015 | £15m)

Chelsea splashed out £15 million on Ghanaian left-back Baba Rahman, who made just 23 appearances for the club between 2015-2023. That's right, Rahman somehow lasted a grand total of eight(!) years at Stamford Bridge.

The defender spent most of that time out on loan, playing for the likes of Schalke, Reims, Mallorca, and Reading. Chelsea finally got the 29-year-old off their books when he joined Greek side PAOK.

8. Nuri Sahin (Borussia Dortmund to Real Madrid | 2011 | £9m)

The £9 million purchase of Nuri Sahin felt like a real coup for Real Madrid in 2011. The Turkish midfielder had shone bright at Borussia Dortmund but, for whatever reason, it failed to happen for him at the Bernabeu.

After failing to impress on loan at Liverpool, Sahin signed for Dortmund on loan before re-joining the Bundesliga outfit permanently in 2014. He made just 10 appearances for Los Blancos, scoring one goal.

7. Ricardo Quaresma (Porto to Inter Milan | 2008 | £22.1m)

It’s such a shame things failed to work out for Ricardo Quaresma at Inter because the Portuguese winger was a serious talent. He scored a hugely disappointing one goal in 32 games for Inter and also underwhelmed on loan at Chelsea before being offloaded to Besiktas in 2010.

Quaresma ended up back at Porto for a year in 2014, and was last seen with the Portuguese side Vitoria de Guimaraes in 2022. To think, he was once considered by some football fans as a more talented player than Cristiano Ronaldo.

6. Mateja Kezman (PSV Eindhoven to Chelsea | 2004 | £5.3m)

Buying prolific strikers from the Eredivisie is unquestionably a gamble. For every Ruud van Nistelrooy or Luis Suarez, there’s an Afonso Alves or, indeed, a Mateja Kezman.

The Serbian striker was signed by Chelsea in 2004 after scoring 38 goals in 43 games for PSV Eindhoven, but struggled to produce the goods in the Premier League, bagging just four goals in 25 games. At the end of his first season at the Bridge, Kezman was moved on to Atletico Madrid.

5. Juan Cuadrado (Fiorentina to Chelsea | 2015 | £23.3m)

Juan Cuadrado proved he was a top-level winger during his time at Fiorentina, which convinced Mourinho to bring the Colombia international to Chelsea in February 2015. After a difficult start, Mourinho told reporters: "He needs time. I know Italy and I know the difference between Italy and England. His formation, his development, his experience – everything was in Italy. Stability, time, integration – I think we will see the best Cuadrado next year."

But we never did. Cuadrado ended up playing just 15 games for Chelsea before joining Juventus permanently in 2017. The 35-year-old then signed for Inter Milan in 2023.

4. Radamel Falcao (AS Monaco to Chelsea | 2015 | Loan)

After Radamel Falcao flopped on loan at Man Utd, Mourinho thought he could bring the best out of the Colombian striker at Stamford Bridge. But, alas, he could not.

Falcao, who was arguably the best No. 9 in the world at his peak, scored one goal in 12 games for Chelsea before his disastrous spell in English football came to an end. The South American went on to resurrect his career, to an extent, with Galatasaray and then Raya Vallecano.

3. Papy Djilobodji (Nantes to Chelsea | 2015 | £4m)

Shortly after Papy Djilobodji’s arrival, Mourinho told reporters it wasn’t his choice to bring the Senegalese defender to Chelsea - which, let’s face it, would explain a lot. That said, Mourinho was still the man in the hot-seat at the time, so Djilobodji officially goes down as one of his signings.

The defender made just one appearance for the Blues before moving on to Sunderland, who ended up sacking him for breaching his contract. The 34-year-old has been with Turkish side Gaziantep FK since 2019, in case you were wondering.

2. Andriy Shevchenko (AC Milan to Chelsea | 2006 | £30m)

In the summer of 2006, when it was announced that Chelsea had signed the world-class Andriy Shevchenko from AC Milan, it felt like the back-to-back Premier League champions were about to become unstoppable. Nobody would have predicted that the revered Ukrainian striker would struggle quite so badly at the Bridge.

Twenty-three goals in 76 games was such a massively underwhelming return from a striker of his calibre - and he’ll always be remembered as one of Chelsea’s biggest flops as a result. It could be argued that his move to west London even damaged his legacy as one of the greatest strikers of his era.

1. Alexis Sanchez (Arsenal to Man Utd | 2018 | (Swap deal for Henrikh Mkhitaryan)

Alexis Sanchez is a strong contender for the unwanted title of Man Utd’s worst ever signing. The Chilean forward, who was handed the club’s famous No. 7 shirt following his shock move from Arsenal, was an unmitigated disaster at Old Trafford.

Five goals in 45 games is all United got in return from a supposedly world-class player on a ludicrous £500,000-a-week contract. It's still baffling when you think how badly he struggled in Manchester. After all, he'd been nothing short of sensational for Arsenal. Some things just aren't meant to be...