The worst transfers in football history

Here we go, then. We all know you’re not reading the intro here. You’ve already skipped straight to the good stuff. And who can blame you? Transfers are great.

Except not always…


For every Cristiano Ronaldo there’s a Juan Sebastian Veron, for every Didier Drogba there’s an Andriy Shevchenko, and for every Fernando Torres there’s a…erm…Fernando Torres.

Just a word on our methodology, before we begin. Bad transfers are ranked based on four key factors: original cost, sell-on fee (or lack thereof), individual (under)performance and off-field issues/general embarrassment to the club.

So without further ado, here’s 90min’s definitive ranking of the 30 worst transfers in football since 2000.

Juan Sebastian Veron of Manchester United

It turns out we were the idiots on this one / Jeff Gross/Getty Images

Approx transfer fee: £28m

Manchester United paid a British record fee to sign Juan Sebastian Verón from Lazio in 2001, and it seemed like good business when he hit the ground running with three goals in his first four Premier League outings. But the pace of English football soon took its toll, and Verón’s performances took a serious nosedive.

“[Verón] is a f*cking great player, and you’re all f*cking idiots,” Sir Alex Ferguson – never one to back down – told the media. However, in 2003 but even SAF conceded defeat and allowed Verón to join Chelsea for half what United had paid Lazio two years before.

The injury-riddled Argentine was no better at Stamford Bridge, making just seven Premier League appearances before returning to Italy.

Yoann Gourcuff

Yoann Gourcuff did not turn out to be the new Zidane / Jean Catuffe/Getty Images

Approx transfer fee: €22m

After a disappointing and short-lived spell at AC Milan, Yoann Gourcuff’s career got a second wind when he joined Bordeaux in 2008. His performances earned comparisons to Zinedine Zidane as he inspired Bordeaux to their first league title in a decade, ending Lyon’s seven-year dominance of Ligue 1.

If you can’t beat them, buy them and Lyon signed Gourcuff for a then-whopping €22m in 2010.

However, much like Jamie Vardy several years later, Gourcuff struggled to adapt to the style of manager Claude Puel, with just three goals in his debut season.

Worse still, Gourcuff missed over 90 games due to injury in his five years at Lyon, and eventually joined Rennes on a free deal in 2015.

Barcelona's new signing Ukranian Dmytro

Who are ya? / LLUIS GENE/Getty Images

Approx transfer fee: €25m

Remember Dmytro Chygrynskiy? What do you mean, no??

The biblical-looking Ukrainian defender kept Barcelona‘s formidable attack at bay for 115 minutes in the 2009 UEFA Super Cup, convincing Pep Guardiola to spend big to sign him from Shakhtar Donetsk as competition for Gerard Pique and Carles Puyol.

Chygrynskiy played just 14 matches in all competitions for Barcelona, before returning to Shakhtar Donetsk at the end of the season.

His name remains a bizarre footnote in an illustrious period of Barcelona’s history.

Jack Rodwell

Is this Sunderland’s worst ever signing? / Stu Forster/Getty Images

Approx transfer fee: £10m

Not a patch on many of the other entries on this list in pure financial terms, Rodwell’s inclusion is more to do with how he became a living, breathing symbol for Sunderland’s excess and mismanagement.

The injury-plagued midfielder managed fewer than 45 league starts in over three seasons, but took home £70,000 a week in wages as the Black Cats plummeted from Premier League regulars to League One meme club and teetered on the brink of financial abyss.

Local papers the Chronicle and Northern Echo both described the former Evertonian as the worst signing in Sunderland history (no mean feat at all) upon his 2018 exit.

Ricardo Quaresma

Inter’s golden bin / Etsuo Hara/Getty Images

Approx transfer fee: €19m

Ricardo Quaresma came through the ranks at Sporting CP around the same time as Cristiano Ronaldo, but their careers would take quite different paths. Quaresma joined Barcelona in 2003 but returned to Portugal with Porto just one year later, where he rediscovered his form in his home country, winning a move to Italy in 2008.

But Quaresma’s ability and attitude both came under the microscope at Inter, with Inter boss Jose Mourinho – famously not a great lover of temperamental forwards – questioning his team ethic.

He was ‘awarded’ the infamous Bidone d’Oro (Golden Bin) award for worst Serie A player at the end of his debut season, and joined Besiktas after two unhappy years which yielded just one Inter goal.


It should’ve worked but it didn’t / Jasper Juinen/Getty Images

Approx transfer fee: €68.5m

It seems implausible that Kaka could ever appear on a worst list of anything. The boyish Brazilian was one of the finest players of his generation, a stylish attacking midfielder whose poise was matched by his power. He was the last player to win the Ballon d’Or before Lionel Messi and Cristiano Ronaldo’s decade of dominance.

Yet, despite becoming the world’s most expensive footballer when he joined Real Madrid in 2009, it soon became evident that Kaka’s best years were behind him.

Injuries marred his first two years at the Bernabeu, during which time Mesut Ozil took his place in the team. Kaka was sold back to Milan in 2013 on what was essentially a free deal.

It remains one of football’s biggest ever transfer losses.


Drink it in / PAUL ELLIS/Getty Images

Approx transfer fee: £16m

Much like Rodwell, the wider symbolism here is more significant than the actual transfer fee.

Mario Balotelli, once touted as one of the continent’s top young talents, was signed by Liverpool to replace Barcelona-bound Luis Suarez, the man who had scored 31 times in 33 Premier League games in the 2013/14 Premier League season and almost dragged his teammates kicking and screaming to the title.

Balotelli scored exactly one Premier League goal for the Reds as Brendan Rodgers’ side collapsed into mediocrity.

He was let go for free, after a loan back to Milan.

Lazar Markovic

Markovic did not have a good time at Anfield / James Williamson – AMA/Getty Images

Approx transfer fee: £20m

Liverpool did some serious business in the summer of 2014.

As well as landing Balotelli, the club gambled on up-and-coming Serbian winger Markovic who had impressed in the previous season’s Europa League.~

Markovic made over 30 appearances in his first season without really impressing but then completely fell off the map at Anfield.

After four loan spells away which failed to boost his profile, he was given away for nothing to Fulham in January 2019.

Shkodran Mustafi

Mustafi became a joke figure by the end of his time in London / Catherine Ivill/Getty Images

Approx transfer fee: £35m

One of the better defenders in La Liga and a World Cup winner no less, Arsenal seemed to have exercised unusually shrewd judgement in signing Mustafi from Valencia in 2016.

After a promising start, Mustafi became a by-word for comical defending as the toe-curling errors came thick and fast. As did the unflattering social media compilations.

The German, who left for Schalke after having his contract mutually terminated in 2021, symbolised the poor recruitment that plagued Arsenal at the end of Arsene Wenger’s tenure.

Angel di Maria

Di Maria’s stint in Manchester with brief and unspectacular / Michael Regan/Getty Images

Approx transfer fee: £60m

Thirteen years on from Juan Sebastian Veron, Manchester United once again broke the British transfer record to sign an Argentine midfielder, and Angel Di Maria continued the symmetry by failing to shine at Old Trafford, despite arriving from Real Madrid with a formidable reputation.

He started brightly, winning Manchester United’s player and goal of the month awards for September, but that soon tailed off and he was named the Telegraph’s worst signing of the 2014/15 season (some feat considering Liverpool’s haul that summer).

He left after just one season for a loss of over £15m.

Frustratingly for the Red Devils, he is now an integral player for PSG and Argentina, with that one-year spell in England pretty much the only blip in his career.


Mangala waiting for the fans to sing his name / OLI SCARFF/Getty Images

Approx transfer fee: £42m

What a summer 2014 was!

A mind-boggling amount of money, Mangala could never live up to his price tag at the Etihad, but he might at least have given it a go…

On his second league outing he scored an own goal and conceded a penalty to throw away a 2–0 lead against Hull, while a couple of months later he suffered his first sending off.

Things never really recovered from there for one of the Premier League’s most expensive ever defenders, who was replaced by Nicolas Otamendi and left on a free in 2019 after a couple of loan spells.

Leonardo Bonucci

Bonucci is Milan colours is just weird / Marco Luzzani/Getty Images

Approx transfer fee: €42m

In an eye-catching summer of business that included the arrivals of Hakan Çalhanoğlu and Lucas Biglia, the signing of Bonucci from rivals Juve seemed like the most impressive of all.

One of the world’s best defenders was looking for a new challenge, after years of domestic (if not European) success in Turin.

Things did not go to plan, and Milan – for all their spending – wound up finishing sixth, while Bonucci, who had been made Rossneri captain, spent the year with an expression that read ‘I’ve made a huge mistake.’

Back he went to Juve after just one year for the princely sum of one Mattia Caldara.

Chelsea's Spanish striker Fernando Torre

A familiar look for Fernando Torres during his Chelsea days / AFP/Getty Images

Approx transfer fee: £50m

On the face of it, this looked like an incredible piece of business for Chelsea, stealing one of the Premier League’s most lethal strikers from rivals Liverpool on deadline day, but for whatever reason Torres’ ill-fated spell with the Blues never reached the heights he had achieved at Anfield.

In fairness, Torres did score 45 times for Chelsea, including the goal which confirmed their place in the 2012 Champions League final, but he never scored more than eight goals in a Premier League season at Stamford Bridge and was a shadow of the world class front man Liverpool and Spain had gotten in the years previously.

Adrian Mutu

Adrian Mutu’s off-field issues stopped him becoming a success at Chelsea / Stu Forster/Getty Images

Approx transfer fee: £16m

With just six goals in 27 Premier League appearances for Chelsea (four of which came in his first three games), Mutu never delivered on the potential he had shown in Serie A with Verona and Parma, while he was one of many to endure a difficult relationship with Jose Mourinho.

But let’s be honest, Mutu isn’t on this list because he was a bad footballer.

In September 2004, Mutu was banned from football for seven months after testing positive for cocaine. Chelsea sought compensation for a breach of contract and a long-winded legal battle ensued.

In 2018, the European Court of Human Rights rejected Mutu’s appeal against CAS 2015 ruling that meant he owed Chelsea €17m in damages.

Jese Rodriguez

Oh Jese. / Jean Catuffe/Getty Images

Approx transfer fee: €25m

In May 2016, Jesé Rodriguez was on the bench for Real Madrid in the Champions League final. In August 2017, he joined Stoke City on loan. His annus horribilis started with a €25m move to Paris Saint-Germain, and from there he was soon sent on loan to Las Palmas after six months of injuries and poor form.

In total, Jese played just 18 times for PSG across four seasons before having his contract cancelled amid COVID lockdown breach scandal in December 2020.

Jonathan Woodgate

The debut to end all debuts / Denis Doyle/Getty Images

Approx transfer fee: £13.5m

Some players have their careers disrupted by injury; Jonathan Woodgate’s career was one long injury disrupted by occasional periods of fitness.

To the surprise of absolutely nobody, Woodgate got injured at the end of the 2003/04 season, but what was surprising was that this did not stop Real Madrid from signing him.

Numerous injury complications meant that Woodgate didn’t actually make his Real Madrid debut for over a year, but boy was it worth the wait.

The former Newcastle star scored an own goal after 26 minutes and was sent off for a second bookable offence midway through the second half.

After just nine La Liga appearances, Woodgate returned to England, having been named the worst signing of the 21st century in a Marca poll.


Joelinton pointing to where his hopes and dreams have gone / Pool/Getty Images

Approx transfer fee: £40m

Newcastle fans spent a decade pleaded with their unpopular owner Mike Ashley to spend big, and when he finally did they wished he hadn’t bothered.

Joelinton, still young but never prolific, was recruited from Hoffenheim to be the Toon’s shiny new front man in a club-record deal.

To date he has a pretty measly six goals in 69 Premier League appearances, has struggled to adapt to the English game and even suffered the indignity of having the number nine shirt taken off him and given to Callum Wilson instead.

Jackson Martinez

Martinez marked the height of mad Chinese spending / Aitor Alcalde Colomer/Getty Images

Approx transfer fee: €42m

In reality, Martinez could’ve mad the list for two separate deals.

Despite having seen the once prolific Colombian flounder at Atletico Madrid (where he scored just three times in 22 appearances) Guangzhou Evergrande decided this was the striker for them to go big on.

At the height of the Chinese Super League’s new spending power, Guangzhou paid €42m to bring Martinez to Asia – amazingly some €7m more than Atleti paid the year earlier before he flopped. Diego Simeone must’ve thought it was some sort of prank.

Martinez, who was famously on a €12m deal, suffered horrendous luck with ankle injuries in China and made just 16 appearances in three seasons before his contract was cancelled.

Luka Jovic

Jovic’s Real Madrid stint was brief but eventful / Soccrates Images/Getty Images

Approx transfer fee: €60m

Young Serbian became one of the hottest forwards in 2018/19, scoring 27 goals at Frankfurt.

Real Madrid paid big, in their last big spending spree pre pandemic, to bring him to the Bernabeu as cover/a long-term successor for Karim Benzema.

In his first season, Jovic struggled with injuries and was given precious little chance to impress, scoring just twice in 27 outings.

Then came the pandemic and a lockdown breach scandal that even involved the Serbian Prime Minister.

A way back into Madrid’s good books looks next to impossible now – as does being able to recoup much of that €60m outlay.

Andy Carroll, Kenny Dalglish, Luis Suarez

Two of these men were quality Liverpool strikers / Alex Livesey/Getty Images

Approx transfer fee: £35m

The panic buy to end all panic buys?

Carroll had scored 11 goals in 19 appearances for Newcastle in the 2010/11 season, catching the eye of Liverpool, who needed to replace the Chelsea-bound Torres.

While Liverpool’s other signing in the January window, Luis Suarez, was an instant hit, Carroll was such an obvious case of a square peg fitting a round hole.

The injury-troubled target man scored just six Premier League goals in 44 appearances before West Ham took him off Liverpool’s hands in 2013 – for close to £20m less than the Reds had paid two years earlier.

Even in the inflated markets of 2019, Carroll is still the most expensive English striker ever.

Perugia v Lazio X

Mendieta in his pre-Boro days / Grazia Neri/Getty Images

Approx transfer fee: €48m

There was a time when Valencia were considered one of the best teams in Europe, and Gaizka Mendieta was their beating heart. He was named Best Midfielder in Europe by UEFA two years on the trot, and when Lazio signed him in 2001, they made him the sixth most expensive player of all time with a deal worth an incredible sounding eight billion pesetas.

In today’s money, the deal would’ve been worth close to the €100m mark.

However, after betting the farm on their man, Mendieta, who had been a regular goalscorer towards the end of his time at the Mestalla, failed to hit the target once in 31 appearances for the Biancocelesti, who offloaded him to Barcelona after just one season.

Zlatan Ibrahimovic

Lions don’t something something… / Denis Doyle/Getty Images

Approx transfer fee: £59m + Samuel Eto’o

Zlatan Ibrahimovic has scored goals everywhere he has played, and Barcelona was no different – in his defence, he found the net 21 times in his only full season at Camp Nou.

But the problems were all off the pitch. Firstly, no-one seemed to understand why Barcelona spent big and traded Samuel Eto’o for the big Swede and his big ego.

While Eto’o went on to win the treble at Inter, Zlatan was (allegedly) threatening to physically assault Pep Guardiola.

Forced to play in the shadow of Lionel Messi, Ibrahimovic grew frustrated and aggro. As a result, he was sent back to Italy at the end of the season.

Andriy Shevchenko

Shevchenko became a regular sub after his first season at Chelsea / Gary M. Prior/Getty Images

Approx transfer fee: £30m

If ever there was a striker worth breaking the bank for, it was Andriy Shevchenko. A prolific goalscorer in Italy, he scored 173 goals during his first spell with AC Milan, surpassing the 25-goal mark in six of his eight seasons at San Siro, and won the Ballon d’Or in 2004.

Signing the Ukrainian became a pet project for Chelsea owner Roman Abramovich, who got his man in 2006 – regardless of what Mourinho actually wanted.

Alas, Shevchenko’s ageing limbs and the pace of English football did not agree with one another. He found the net just nine times in the Premier League before retracing his steps to Milan and Dynamo Kiev as his brilliant career ended with a whimper.

Danny Drinkwater

Drinkwater receiving red in a PL2 game / Justin Setterfield/Getty Images

Approx transfer fee: £35m

Continuing the run of Chelsea flops, it is Drinkwater, whose £35m move to Stamford Bridge in 2017 raised eyebrows even before a ball was kicked in anger.

The former Premier League winner with Leicester made just 12 league appearances and found himself rather unloved by Antonio Conte and latterly Maurizio Sarri.

Amid a series of uninspiring loan spells, Drinkwater’s on-field nadir came with a brawl-sparking red card in a PL2 game against Spurs in 2020.

Off the field, unsavoury incidents including a drink driving charge and a nightclub fight that left him with ligament damage have coloured a once respected career.

Alexis Sanchez

Was it worth it? / Chris Brunskill/Fantasista/Getty Images

Approx transfer fee: Swap with Henrikh Mkhitaryan

How can a deal that involved no real transfer fee be so bad, you ask? Well…

Alexis Sanchez arrived at Manchester United as perhaps the Premier League’s biggest talent, ripped from rivals Arsenal with his contract running down. To add a cherry on top, United even beat off competition from Man City to land the Chilean.

In order to convince Sanchez to pick red over blue, United stumped up a contract worth depressingly close to £500k a week before plonking their new forward in front of the piano for what would become one of the most infamous announcement videos of all time.

Sanchez’s contract became an albatross around his neck as his form dived off a cliff.

In total, he scored three Premier League goals in 32 outings and generally stunk Old Trafford up, before being loaned out to Inter where he now resides permanently, having had his whopper of a United deal paid off early.

Kepa Arrizabalaga

Kepa is a Champions League winner / David Ramos/Getty Images

Approx transfer fee: £72m

Six months after Real Madrid almost landed the promising Basque stopper for around £20m, Chelsea – in the wake of Thibaut Courtois’ departure – panicked and paid the full release clause for 23-year-old Kepa Arrizabalaga.

A world-record fee for a goalkeeper, Chelsea’s purchase raised eyebrows which weren’t lowered by Kepa’s unconvincing displays.

Though he impressed in the Blues’ Europa League run and triumph, his league form never matched the price tag. Meanwhile, stats about just how bad his save percentage was continued to do the rounds on social media.

Then after that League Cup final incident with Maurizio Sarri, where he refused to be substituted, things took a dramatic turn for the worse.

He goes into the 2021/22 season as probably the Premier League’s most expensive bench warmer, having been usurped by new keeper Edouard Mendy.


There are wastes of money and there are Tevez in China wastes of money / STR/Getty Images

Approx transfer fee: €16m (transfer fee is disputed)

In December 2016, Carlos Tevez left his boyhood club Boca Juniors for a second time to join Chinese Super League side Shanghai Shenhua, who reportedly paid him an annual salary of £630,000 a week – supposedly making him the highest paid player in all of world football.

Tevez himself disputed those claims telling reporters not to believe the ‘legends’.

Shenhua were hoping that a superstar like Tevez, who had shone in England, Italy and Argentina, would help them win a first league title since 1995, but the controversial forward had different priorities.

Tevez played just 20 times in his one season in China, scoring four (working out at roughly £8m a goal), while he appeared to be unfit and uninterested.

The former Man City star later described his time in China as a ‘holiday’, while Shenhua fans booed him and gave him the nickname ‘homesick boy’.

As a parting shot on his return to Boca, Tevez claimed Chinese players are ‘not as naturally skilled like South American or European players’ and added that ‘even in 50 years, they still won’t be able to compete.’

Ousmane Dembele

The first 100m flop? / Quality Sport Images/Getty Images

Approx transfer fee: €105m (rising to €145m with add-ons)

Dembele has the unwanted distinction of perhaps being football’s first 100m flop.

The French winger shone in a breakthrough season at Dortmund, which convinced Barcelona to go big with their new Neymar money burning a hole in their pockets.

Though there have been flashes of brilliance here and there, injuries and reports of discipline problems marred Dembele’s first four seasons at Camp Nou.

in total he missed a ridiculous 85 games between 2017 and 2021 through injury, while reports that he skipped training after staying up all night to play video games did his reputation no favours.

Now as Barça teeter on the brink of financial chaos, Dembele’s huge-money signing looks like a prime example of the dangerous spending under former president Josep Maria Bartomeu.

Philippe Coutinho

Coutinho helping knock his own club out of the Champions League / Pool/Getty Images

Approx transfer fee: £105m (rising to £142m with add-ons)

Incredibly though, Demeble’s transfer is not Barcelona’s worst of all time. That ‘honour’ has to fall upon Philippe Coutinho who has not only failed to perform consistently in a Barça shirt, but played an active role in knocking them out of the 2019/20 Champions League.

Much like with Dembele, Barcelona overpaid to get their man following Neymar’s traumatic departure, but struggled to come to terms with the fact that Coutinho simply was not Neymar.

Despite some reasonable showing in his first two seasons, it became clear that Barça didn’t really have a role for Coutinho and loaned him out to Bayern Munich… and we all know what happened there.

Coutinho, now back in Catalonia, remains virtually unsellable due to his wages, even if Barça are willing to accept a massive loss on a price tag they are still paying off three years on.

Eden Hazard

Where did it all go wrong? / Soccrates Images/Getty Images

Approx transfer fee: €100m (rising to €146m with add-ons)

Signed as the marquee replacement for Cristiano Ronaldo at the Santiago Bernabeu, the really strange thing was that Madrid could simple have waited a year and got Hazard on a free.

They didn’t though, essentially paying north of €100m for the one goal he scored in the entirety of the 2019/20 season.

The now 30-year-old (who is reportedly on £400,000 a week) has been riddled with injuries since arriving in Spain, but did not win fans over by arriving for pre-season seven kilos overweight and later laughing with Chelsea stars as they knocked Real Madrid out of the Champions League.

He’s been so disastrous that he may end up making perma-angry El Chiringuito pundits nostalgic for the return of Gareth Bale.

Read here for more about just why this is the worst transfer of all time.

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Author: XenBet

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