A disaster from start to finish.

The 10 worst signings of Jose Mourinho’s career: Sanchez, Shevchenko, Cuadrado…

Jose Mourinho will go down as one of the greatest managers in the modern game, but he’s made some very questionable signings throughout his career.

The ‘Special One’ has divided opinion ever since he burst onto the scene with Porto and then took the Premier League by storm with Chelsea. Doing whatever it takes to win proved effective for a while in his career, even if it meant winning ugly, but also required a very specific type of recruitment – and not the good kind.

You’re either a Mourinho guy or you’re not. He’s always tried to sign players who would run through walls for him, but being so divisive, it hasn’t always worked. We’ve looked back at the 10 worst signings Mourinho has made throughout his otherwise illustrious career thus far.

Joe Rodon

When Tottenham snapped up 22-year-old Rodon from Nottingham Forest in 2020, it looked like Mourinho had done it again with another young and promising defender.

Earning rave reviews for his ascent in the Championship, it felt like shrewd business. Rodon never really kicked on, though, getting lost in the shuffle that came with the entire fever dream that was Mourinho at Spurs and eventually falling completely out of favour.

The Wales international, now 26, has since rediscovered his form in the Championship on loan at Leeds United after a less than impressive stint in France with Rennes. It would make sense for all parties if a permanent deal could be completed, even if Spurs have to take a loss on the initial £11million they paid.

Khalid Boulahrouz

An unknown quantity at the time, Mourinho had the stock to sign whoever he wanted at Chelsea by 2006 after back-to-back Premier League title wins.

Alarm bells should’ve started ringing immediately, however, when new defensive signing Boulahrouz was given the number nine shirt after his £8.5million move from Hamburg. It was doomed from the off.

A briefly bright start very quickly fizzled out due to injury and inconsistency. It became apparent that the Dutch international would not be the heir to Ricardo Carvalho’s throne. He left on loan after just one season and was sold after just two years.

Ricardo Quaresma

Quite possibly the best and least chaotic stint of his career, there isn’t much you can critique Mourinho for at Inter. Their 2008 purchase of Quaresma was a small blemish, however.

Signing in a player-plus-cash deal (remember those?) he marked his Serie A debut with a trademark trivela goal. Unfortunately, he struggled to break into the starting XI and for good reason when you look at what the likes of Zlatan Ibrahimovic, Samuel Eto’o and Wesley Sneijder all achieved together.

Quaresma was unfortunately awarded with the Bidone d’oro award at the end of the 2008-09 campaign, a tongue-in-cheek award given out on Italian radio station Catersport to the most disappointing player in Serie A.

He stuck around for Inter’s treble-winning season of 2009-10 – and donned the number seven shirt, strangely – despite the club trying to get rid of him. Quaresma eventually left his Italian nightmare behind in the summer of 2010, signing for Besiktas having won a treble, but having only played 32 times for Inter and scoring one.

Steven Bergwijn

Another one from Mourinho’s increasingly bizarre spell at Spurs, he admitted that Bergwijn wasn’t his first choice after he signed in January 2020, setting the one for an indifferent spell.

Bergwijn made a fast start, notably scoring against Manchester City and earning the Player of the Match award, and bounced back after the COVID-19 break by scoring against Manchester United. But he never really progressed beyond that, only impressing in flashes and failing to kick on.

An inconsistent time in north London came to an end after two years when Spurs sold Bergwijn to Ajax in July 2022 for £26.4million, essentially breaking even on the initial £25million they paid for him.

Rui Patricio

Working with incredibly limited cash for transfers at Roma, £9.8million seemed to represent decent value for money in poaching Patricio from Wolves in 2021.

The Portuguese stopper arrived from the Premier League with experience and a strong reputation which was clear in his first season in Rome as they won the Europa Conference League, but things very quickly fizzled out after that as his form dipped in 2022-23 and even more so in 2023-24.

His regression likely accelerated Mourinho’s sacking and, now 35, Roma will be lucky to recoup any of the fee they paid for him three years ago.

Jose Mourinho celebrates with Roma.

READ: Ranking every stint of Jose Mourinho’s career from worst to best: Man Utd, Chelsea, Real Madrid…

Juan Cuadrado

Signed off the back of an impressive showing for Colombia at the 2014 World Cup, Cuadrado set Chelsea back an initial £23.3million, potentially rising to £26.8million with add-ons, when they snapped him up from Fiorentina in January 2015.

Considering the winger made just 13 Premier League appearances after signing, failed to score in any of them and was sent back to Serie A with Juventus by August, it’s fair to presume those add-ons weren’t met.

A complete waste of everybody’s time and money. Far from Mourinho’s finest spot.

Baba Rahman

Sticking with Mourinho’s second spell at Chelsea, Rahman was signed in the summer of 2015 from Augsburg after the Blues had lifted the Premier League once more.

Mourinho parted with an initial £14million for Rahman, rising to £22million, in a bid to bolster his title-winning squad with some youthful exuberance. The Ghana left-back would spend the next eight years on the books at Chelsea, spending the vast majority of that time out on loan.

After playing 24 times in all competitions in a perilous 2015-16 campaign, Rahman’s Chelsea career effectively came to an end after that. You’d be forgiven for being shocked at the fact that he only officially left the club last summer, aged 29. Absurdity.

Fabio Coentrao

Signed for Real Madrid in 2011 when Marcelo was on a journey towards becoming one of the greatest full-backs of all time, Coentrao was used as a utility man in his first season at the club.

A rotation arm in Mourinho’s record-breaking side, the Portuguese full-back quickly failed to live up to his £27.1million price tag and slid down the pecking order in the following two seasons.

Mourinho had left by 2013, but Real couldn’t shift Coentrao until 2018, sending him on a series of loans before finally leaving for nothing. Nightmare.

Andriy Shevchenko

Off the back of winning the Premier League, splashing the cash to sign Milan’s second-top scorer of all time didn’t seem too terrible an idea in a bid to build a squad of superstars.

But there was a catch – Mourinho didn’t actually want him. It was the signing that spelled the beginning of the end and it wasn’t even worth it.

14 goals from 51 games was a disappointing return in his debut season, and his 2007-08 campaign coincided with Mourinho’s departure, resulting in another season of injury and inconsistency.

He was back on loan at Milan in his third season, before leaving Chelsea in 2009 to return to Dynamo Kiev. What a mess.

Chelsea's Andriy Shevchenko and Jose Mourinho, 2007.

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

Alexis Sanchez

Doomed from the minute he sat down to play that piano, Sanchez was the very peak of Manchester United’s banter era.

With Manchester City keen to sign the Chilean from Arsenal in January 2018, United swooped in at the death, dwarfed their contract offer with eye-watering wages and offered Arsenal Henrikh Mkhitaryan – who almost made this list, in fairness – in exchange, which got the deal over the line.

Sanchez quickly realised life at United wasn’t what it seemed, asking his agent after one training session if the deal could be reversed. He looked like a square peg in a round hole from the off and never looked like coming good as Mourinho’s reign fizzled out throughout 2018 before his inevitable dismissal.

Unsurprisingly, Ole Gunnar Solskjaer also couldn’t get a tune out of the attacker, whose heart wasn’t in it and whose legs appeared to have gone. City dodged a bullet thanks to the Special One – and probably United’s laughable management.

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