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Top 15 worst transfers in football history (2024)

Generally Massive spending can sometimes lead to success in Football, but indiscriminate splurging doesn’t always yield positive outcomes. Despite this, affluent clubs are always eager to shell out cash to solve problems or recruit players, often resulting in colossal signings that end up as disappointments.

Numerous players acquired for hefty fees fail to meet expectations. Several factors contribute to this, such as joining a club at an inopportune time, working under unsuitable management, the burden of a lofty transfer fee, individual underperformance, and off-field issues.

1. Antoine Griezmann (Atletico Madrid to Barcelona, 2021)

Approx transfer fee: €120m

For Barcelona though, signing Antoine Griezmann has proved to be the worst business they’ve ever done. And in 90min’seyes, the worst transfer in the history of football.

They paid Griezmann’s release clause outright in summer 2019, in the peak years of the club being an absolute mess under Josep Maria Bartomeu, with the existing squad of players reportedly against the signing and the management actually having no idea of where to play him.

The Frenchman had a generally miserable time of it in his two years at Camp Nou, and was put on a contract so big that it eventually contributed to the club not being able to commit to a new contract for Lionel bloody Messi.

Barcelona lost their greatest ever player to PSG because of the financial mess they’d put themselves in (this transfer was a huge factor), and in the end decided to cut their losses on Griezmann too.

He went on loan to Atletico Madrid, with an option to buy for €80m less than what they sold him for. Oh, and they beat Barcelona to the league title in 2021 too – with another player they picked up from Camp Nou for chump change in Luis Suarez.

2. Eden Hazard (Chelsea to Real Madrid, 2019)

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. He had a total of five for Los Blancos by the start of 2021/22, and literally more injuries.

The now 31-year-old (who is reportedly on £400,000 a week) 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 in 2021.

3. Philippe Coutinho (Liverpool to Barcelona, 2018)

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, Ousmane Dembele’s transfer is not Barcelona’s worst of all time… though nor is Philippe Coutinho’s to be fair.

The Brazilian was still awful, though. He not only failed to perform consistently in a Barca 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 Barca didn’t really have a role for Coutinho and loaned him out to Bayern Munich…and we all know what happened there.

He now now playing in saudi Arabia and has not made any good impact so far

4. Romelu Lukaku (Inter to Chelsea, 2021)

Approx transfer fee: £97.5m

Romelu Lukaku’s glorious return to Chelsea was unfinished business.

He’d been sold by the Blues, the club he’d loved since he was young, early on in his career, and after an underwhelming spell at Man Utd had found his groove at Inter under Antonio Conte.

Lukaku scored a ton as Inter won the league, and when Chelsea paid just shy of £100m for him in 2021 he was tipped to do the same for them.

Instead, he scored a few goals against inferior opposition, did an interview with Sky Italia about how much he missed Inter & moaned about not being played to his strengths at Chelsea, before being frozen out of the team by Thomas Tuchel.

Chelsea, desperate to part ways, have now shifted Rom back to Inter for a loan fee around a tenth of the fee agreed with Inter a year prior. Awful stuff.

Somehow he’s now playing in Roma and has been making few impact.

5. Ousmane Dembele (Borussia Dortmund to Barcelona, 2017)

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.

He has now left Barcelona to join Paris saint german , he recently scored against Barcelona and celebrates which doesn’t sit well with the Barca fans

Top 10 football players who celebrated after scoring against their former clubs

6. Alexis Sanchez (Arsenal to Manchester United, 2018)

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.

7. Paul Pogba (Juventus to Man Utd, 2016)

Approx transfer fee: £89m 

Now that Paul Pogba has left Manchester United, there can’t be any doubt – his £89m move to Old Trafford in 2016 was absolutely rotten.

Forever a case of unfulfilled potential, Pogba only managed to show his best form for very brief spells in the six years of his second stint in the north west…what we saw more of was unhappiness, poor effort levels and a continued narrative of “I want to leave”.

And leave he did in 2022.

Pogba is a United academy product that left the club for free once, joined Juventus, rejoined United for a then world record fee of £89m, and then left for Juventus again…for free.

If you want a summary of just how bad Man Utd are at transfers, look no further.

He’s now banned in football for 2 years

8. Danny Drinkwater (Leicester to Chelsea, 2017)

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.

He joined Reading on loan in summer 2021.

9. Kepa Arrizabalaga (Athletic Club to Chelsea, 2018)

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.

10. Fernando Torres (Liverpool to Chelsea, 2011)

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.

11. Angel Di Maria (Real Madrid to Manchester United, 2014)

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.

12. Harry Maguire (Leicester to Manchester United, 2019)

Seen that look before, mate / Visionhaus/GettyImages

Approx transfer fee: £80m

Man Utd spent almost an entire summer trying to sign Harry Maguire back in 2019, haggling with Leicester City to drop their £80m asking price. 

In the end, United wasted weeks and paid the full asking price anyway. 

They went on to install him as club captain so prematurely that it now looks as if he might lose it, while more clips of Bad Harry Maguire Defending than you can count have circulated on social media with the caption “What £80m gets u nowadays loooool”.

It’s hard to not feel sorry for Maguire, really. He’s a better player than he’s shown in recent months but £80m heaped a bunch of pressure on him that he just hasn’t been able to handle.

13. Arthur & Miralem Pjanic (Barcelona swap with Juventus, 2020)

Arthur still features for Juventus but Pjanic is a Barcelona outcast / Nicolò Campo/GettyImages

Approx transfer fees: £66m & £59.4m

Perhaps the most unique entry on the list, here, given we’ve got two players in one slot.

At the height of the coronavirus pandemic, Barcelona and Juventus engaged in what was essentially a swap deal to send an average midfielder the other way.

Unsurprisingly, neither of them were any good.

14. Nicolas Pepe (Lille to Arsenal, 2019)

Approx transfer fee: £72m

Social media became unbearable the day Arsenal unveiled Nicolas Pepe as their new record signing. It was even worse a few weeks later when he dribbled past Virgil van Dijk and fooled people into thinking he was going to be a superstar.

In the red of Arsenal, Pepe has looked a lot like an annoying five-a-side teammate, endlessly dribbling down dead ends, never knowing when to release the ball and barely contributing anything tangible to games.

15.Sebastien Haller (Eintracht Frankfurt to West Ham, 2019)

Sebastien Haller

Approx transfer fee: £45m

Sandwiched between Sebastien Haller’s prolific spells at Eintracht Frankfurt and Ajax was a less than fruitful experience at West Ham.

The Hammers’ struggles to find a top class striker have long been documented, and they thought their prayers had been answered when they brought in Haller, who at that time had not declared for the Ivory Coast and was on the verge of a France call-up.

But the lanky forward failed to consistently find the net in claret and blue and was sold to Ajax 18 months later, since re-establishing himself as a quality striker.


Top 10 biggest flop in history

Renato Sanches: Benfica to Bayern Munich (2016) – €35m

Gonzalo Higuain: Napoli to Juventus (2016) – €90m

Kaka: AC Milan to Real Madrid (2009) – €68.5m

James Rodriguez: Monaco to Real Madrid (2014) – €80m

Eliaquim Mangala: Valencia to Manchester City (2014) – £42m

Luka Jovic: Eintracht Frankfurt to Real Madrid (2019) – €60m

Diego Costa (Chelsea to Atletico Madrid, 2017)

Tanguy Ndombele (Lyon to Tottenham, 2019)

Tiemoue Bakayoko (Monaco to Chelsea (2017)

Giovani Lo Celso (Betis to Tottenham, 2019)

Juan Sebastian Veron (Lazio to Manchester United, 2001)

Dmytro Chygrynskiy (Shakhtar Donetsk to Barcelona, 2009)

Jack Rodwell (Manchester City to Sunderland, 2014)

Ricardo Quaresma (Porto to Inter, 2008)

Mario Balotelli (AC Milan to Liverpool, 2014)

João Felix: Benfica to Atletico Madrid (2019) – £113m

Andy Carroll: Newcastle United to Liverpool (2011) – £35m

In summary, while spending big can sometimes be fruitful, it often fails to guarantee success, as evidenced by these high-profile flops in soccer history.

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