Mourinho has made some big signings over the years

Where are they now? Jose Mourinho’s most expensive signing from every season since 2010

Jose Mourinho is undoubtedly one of the greatest managers of all time and throughout his illustrious career, he’s spent plenty of money in the transfer market.

While the Special One never tends to stick around in one place for long, he always leaves a significant mark on the clubs that he’s managed.

We’ve gone back through Mourinho’s career and have found his most expensive signing from every season since 2009-10 to see where those players are today.

2009-10: Diego Milito

Inter Milan had a transfer window for the ages in 2009-10. Signing the likes of Milito, Wesley Sneijder and Samuel Eto’o, it’s no wonder they managed to win the treble.

Of the star-studded arrivals from that summer, Milito was the most expensive at around €38million. He was worth every penny too as he bagged 30 goals across all competitions to help Inter win a historic treble.

Milito went on to spent five years at Inter before he played out the final years of his career in Argentina and retired in 2016. Upon retiring, he became the sports manager at Racing Club, although he left that role in 2020.

2010-11: Angel Di Maria

Mourinho was allowed to splash the cash during his first season at Real Madrid and his most expensive signing that summer was a fresh-faced Di Maria.

The Argentine playmaker quickly became a hit in Spain by producing 35 goal contributions in his debut season. He went on to spend four years at the club and won six trophies during that time.

Then following spells with Man Utd, PSG and Juventus, he now finds himself back at Benfica where he’s still going strong today. Now aged 36, Di Maria has been ageing like a fine wine.

Argentina's Lionel Messi (left) and Angel Di Maria celebrate with the FIFA World Cup Trophy following victory over France via a penalty shootout in the FIFA World Cup Final match at the Lusail Stadium in Lusail, Qatar. Picture date: Sunday December 18, 2022.

READ: Angel Di Maria names his best XI of team-mates: Cristiano Ronaldo nowhere to be seen…

2011-12: Fabio Coentrao

Things never quite worked out for Coentrao at Real Madrid. He arrived under Mourinho for a fee of around £25million, but struggled to dislodge Marcelo from the starting XI.

After spending seven years warming the bench, he eventually left in 2019 to rejoin boyhood club Rio Ave. He eventually called it quits on his football career in 2021 and has since gone into a more modest industry.

Following in the footsteps of his father, the Portuguese full-back has become a shipowner fisherman in his post-playing days and he seems to enjoy his time at sea.

“Life in the sea is not a shame, as many people think,” he told Empower Brands Channel. “It is a job like any other. Not only that, the sea is beautiful and we need it. People who love the sea and who want to experience the sea need to follow their dream.

“It is also a job for the new generations. My father had a boat, he used to fish and I always went with him as a child. My life was the sea… the sea and fishing.”

2012-13: Luka Modric

Looking back on this transfer, it seems utterly bonkers that Modric was voted as the worst signing in La Liga for 2012-13.

Sure, he endured a rocky start at the Santiago Bernabeu, but the Croatian quickly won over the doubters. Fast forward to 2024 and it’s reasonable to suggest that Modric makes it into an all-time Real Madrid XI.

With his contract set to expire at the end of the season, it looks more than likely that he’ll be leaving at the end of the season. There’s no question that he’ll leave the club as a legend.

2013-14: Willian

Chelsea swooped in at the final hour to sign the Brazilian winger shortly after he’d completed a medical with Tottenham. After racking up over 300 appearances for Chelsea, there’s no denying this transfer was a roaring success.

Even today aged 35, Willian is still doing the business in the Premier League for local rivals Fulham.

READ NEXT: Where are they now? Jose Mourinho’s 15 signings at Real Madrid

TRY A QUIZ: The Ultimate Jose Mourinho Quiz: 30 tricky questions to test your knowledge of the Special One

2014-15: Diego Costa

Costa and Mourinho was always going to be a match made in heaven, wasn’t it? After arriving in the summer of 2014 for £32million, Costa immediately hit the ground running.

The powerful forward bagged 20 league goals in his debut season and fired Mourinho’s side to the league title in the process.

He’s no longer at the peak of his powers, but you’ll be pleased to know that he’s still bagging goals to this day for Gremio in Brazil.

2015-16: Pedro

Perhaps one of Mourinho’s most underrated signings. Pedro didn’t get that much of a chance to play under the Special One as Mourinho was sacked just a few months after he’d signed the Spanish winger.

However, Pedro went on to become a key player under Antonio Conte and Maurizio Sarri, winning three trophies with the club along the way.

Even at 36, Pedro is still cutting it at the top level. He’s racked up 42 appearances at Lazio this season, although a return to Spain has been rumoured ahead of next season.

2016-17: Paul Pogba

Signed for £89million in the summer of 2016, Pogba remains the most expensive signing of Mourinho’s career to date. While the Frenchman certainly had his moments playing under the Portuguese boss, the pair didn’t always see eye to eye.

His return to Juventus hasn’t exactly gone to plan either. After spending a year and a half on the treatment table, he received a four-year ban earlier this year after being found guilty of doping.

READ: A timeline of Paul Pogba and Jose Mourinho’s turbulent relationship

2017-18: Romelu Lukaku

Lukaku’s time at Old Trafford isn’t remembered in a particularly fond fashion, but his record of 42 goals in 96 appearances is by no means disastrous.

Upon selling him to Inter Milan in 2019, Man Utd also managed to make most of their money back on the Belgian striker.

The less said about his return to Chelsea the better, although he’s managed to rekindle his goalscoring touch on loan at Roma this season. Still on the books of Chelsea, it remains to be seen where Lukaku’s long-term future lies.

2018-19: Fred

According to reports from the Daily Mail in 2019, Mourinho ‘never wanted Fred’ at Man Utd and he only sanctioned the £52million transfer because he feared the club wouldn’t sign anyone else.

The Brazilian certainly gave his all during his time at Old Trafford, but whether he was worth the £52million transfer fee is still up for debate.

After spending the peak years of his career in England, the Brazilian midfielder joined Fenerbahce last summer.

2019-20: Giovani Lo Celso

Tottenham fans have seen glimpses of Lo Celso’s quality, but it would be foolish to suggest that he’s lived up to the original hype. After originally signing for Spurs on loan under Mauricio Pochettino, the deal was made permanent once Mourinho came in.

During his five years in north London, Lo Celso spent a chunk of time out on loan with Villarreal before returning to Spurs in the summer.

These days under Ange Postecoglou, he’s predominately used as a squad player.

James Maddison during the Premier League match between Tottenham Hotspur and Manchester United at Tottenham Hotspur Stadium, London, August 2023.

QUIZ: Can you name Tottenham’s 30 most expensive signings ever?

2020-21: Sergio Reguilon

Spurs thought they’d landed a bargain when they prized Reguilon away from Real Madrid for £32million, but Tottenham fans have never really seen the best of him.

After falling down the pecking order, he’s spent the last two years out on loan and doesn’t seem to have much of a future at the Tottenham Hotspur Stadium.

2021-22: Tammy Abraham

His first season at Roma was absolutely golden. Signed for £34million from Chelsea, Abraham was worth every penny at the time as he bagged 27 goals in his debut campaign.

Unfortunately, he’s never quite been able to hit those same levels since. He’s spent the majority of this season injured and there’s plenty of uncertainty surrounding his long-term future.

Tammy Abraham and Jose Mourinho at Roma.

READ: Where are they now? Jose Mourinho’s first 11 signings as Roma manager

2022-23: Zeki Celik

Despite signing the likes of Paulo Dybala and Nemanja Matic in 2022, Celik was the only player that Mourinho spent a transfer fee on this season.

The Turkish wing-back penned a four-year contract with Roma upon joining the club and is still playing for the Giallorossi today.

2023-24: Leandro Paredes

Signed for a base fee of just over £3million, Paredes was the last permanent signing that Mourinho made as Roma boss. The Argentine midfielder only got to work with Mourinho for a few months before he was dismissed earlier this year.