With players like Romelu Lukaku actively trying to rectify their careers this season after less than favourable moves, the team here at Sportslens decided to sit down and take a look at the worst transfers in football history.
The Worst Transfers in Football History
10. Jonathan Woodgate – Newcastle to Real Madrid
Kicking things off with what remains one of Real Madrid’s more bizarre acquisitions in Jonathan Woodgate.
Before he had even took to the pitch for Los Blancos, the Englishman arrived with a substantial injury that kept him on the sidelines for over a year. Once hailed as “probably the best centre-half I ever played with” by Gary Speed, it seemed Madrid were prepared to spend just over £13m on the then-24-year-old, despite carrying an injury.
Nevertheless, he took to the field 17 months after his arrival in a match against Bilbao, and nothing could prepare the Madrid faithful for the calamity that unfolded. Woodgate found the net with a stunning diving header – only it came at the wrong end – leaving goalkeeper Iker Casillas completely dumbfounded.
To make matters worse, he was then dismissed after 66 minutes, completing one of the worst debuts ever seen to this day. As you can imagine, his Madrid career never took off and was subsequently loaned to Middlesbrough with just 14 appearances to his name.
9. Gaizka Mendieta – Valencia to Lazio
At a time when Valencia were one of Europe’s elite and a force to be reckoned with under manager Rafa Benitez, Gaizka Mednieta was at the heart of their success.
To provide a bit of context, the Spaniard was one of the most sought-after midfielders in world football having been named Best Midfielder in Europe by UEFA two years on the trot. To everyone’s surprise, free-spending Lazio made him the sixth most expensive signing of all-time, in what appeared to be a huge statement of intent in the Roman’s hunt for the Scudetto.
Throughout the season, Mendieta ghosted in crucial moments. At his brilliant best in Spain, he scored between 10 and 20 goals per season, and provided as many assists. In Rome, a stark contrast; 31 games played in all competitions, no goals scored, three assists.
He returned to Spain with Barcelona after just one season Italy.
8. Andriy Shevchenko – AC Milan to Chelsea
Undoubtedly one of the finest marksman of his generation, Andriy Shevchenko arrived at Chelsea with much promise; twice winner of the Capocannoniere award for top scorer in Serie A, the Ukrainian was the complete striker; fast, powerful and deadly in front of goal.
After Roman Abramovich had unsuccessfully tried to bring him in twice before, the Russian finally got his man after a £30m bid was accepted, signalling a power shift from Italy to England in the process.
However, an ageing, burnt-out Shevchenko who had played over 600 times already in his career, struggled with the pace and intensity of the Premier League, finding the net just nine times before retracing his steps to Milan.
7. Alexis Sanchez – Arsenal to Manchester United
Next we have Alexis Sanchez, whose burning desire to leave Arsenal was ultimately the cause of his steep downfall.
The Chilean looked destined for a move to United’s neighbours City, with the prevailing consensus now that he would have thrived in a more ambitious and forward-thinking environment. Nevertheless, the Red Devils managed to acquire arguably the league’s hottest property in a bizarre swap deal, which saw the Gunners receive Henrikh Mkhitaryan in return (also one of the worst transfers in football).
Throughout a frustrating period, he scored three Premier League goals in 32 appearances before being loaned out to Inter where he now resides. A gargantuan £500k-per-week contract seemed to weigh heavy with the media and the United faithful constantly questioning his commitment.
6. Romelu Lukaku – Inter Milan to Chelsea
Romelu Lukaku’s homecoming was far from the dream move it was pegged to be.
The Belgian enjoyed a fruitful stint at Inter Milan, scoring 64 goals in 95 games earning him a huge £100m move back to Stamford Bridge – a full-circle moment perhaps, to a team he perceived as having unfinished business with.
Fast-forward to now, he finds himself back in Italy, on loan at Roma, after a heavily scrutinised season in England where he scored just eight Premier League goals, and bemoaned at how much he missed playing in Italy.
5. Arthur & Miralem Pjanic Barcelona Swap with Juventus
Sneaking in the top five we have a double entry, as we begin our countdown of some of Barcelona’s bizarre behaviour in the transfer window.
After it was revealed former Blaugrana president Josep Bartomeu was guilty of corruption and fraud, this mind-boggling swap deal makes total sense.
In an exchange that saw a supremely talented Arthur who had been likened to Xavi, just 22 at the time, swapped for an ageing Miralem Pjanic, it seemed to signal the beginning of the end for Barcelona.
The Blaugrana also paid £59.4m for Pjanic who made just 19 appearances before being loaned out to Besiktas a year later.
4. Danny Drinkwater – Leicester to Chelsea
Clocking in at number four, we have Danny Drinkwater, whose £35m move to Chelsea back in 2017 raised everyone’s eyebrows.
Off the back of miraculously winning the Premier League title with Leicester, in which he was one of their stand-out performers, Drinkwater made the switch to West London.
Undoubtedly a bizarre acquisition where he was surplus to requirements before he even arrived, he made just 12 league appearances and found himself largely unused by Antonio Conte and Maurizio Sarri.
A string of loan moves to Burnley and Aston Villa, as well as some off-field incidents including a drink driving charge and a nightclub fight, has seen one of the steepest career drop-offs in recent memory.
He is now a free agent.
3. Philippe Coutinho – Liverpool to Barcelona
One of two Barcelona signings that make up our top three, Philippe Coutinho’s move to Barcelona seemed to be a match made in heaven.
The mercurial Brazilian began life in Catalonia in typical fashion, registering an impressive nine goals and seven assists in 22 appearances in the 2017/18 season.
However, he predictably failed to fit into Ernesto Valverde’s pragmatic system that relied heavily on the brilliance of Lionel Messi. He was brought in as an Andres Iniesta replacement, and he doesn’t quite fit that profile. He isn’t a central midfielder, but they didn’t need him in the front three either; they had both Lionel Messi and Luis Suarez at the time.
Brazil manager Tite also revealed he is “painfully shy”, which as you can imagine in a Barcelona dressing room brimming with elite names, would start to weight heavy.
He was loaned out to Bayern Munich in the 2019/20 season after several attempts to offload him, and at a monumental fee rising as high as £140m with add-ons, it can certainly be classed as one of the worst transfers in football.
2. Antoine Griezmann – Atletico Madrid to Barcelona
While Antoine Griezmann was certainly a better servant to Barcelona than Philippe Coutinho, the Frenchman never quite redeemed the astronomical price tag he arrived with.
It seemed to be a signing spearheaded by, you guessed it, Barcelona’s former President Josep Bartomeu. With several Barcelona mangers not sure where to play him, and players in the dressing room reportedly firmly against the transfer, it would seem the £110m investment was nothing more than a commercial passion project.
As time would tell, this transfer almost certainly contributed to the dire economic situation the club now find themselves in.
35 goals in 102 appearances certainly doesn’t warrant one of the heftiest price tags ever seen, and you have to question whether this transfer affected the club’s inability to keep hold of the greatest player of all time, Lionel Messi. While not directly Griezmann’s fault, the suggestion is the repercussions of this transfer have sent ripples still being felt today.
1. Eden Hazard – Chelsea to Real Madrid
And so, we arrive at what we believe to be the worst transfer in football history..
After Cristiano Ronaldo’s exit at Los Blancos, Florentino Perez was eager to bring in long-term target Eden Hazard who looked set to usher in a new period of success at the Bernabeu.
While they have indeed gone on to do exceptionally well in Hazard’s presence – including two La Liga titles, a Champions League triumph and a Copa Del Rey last season – the Belgian featured sporadically since his arrival after a string of substantial injuries. He managed just 76 appearances since making the switch in the summer of 2019.
A stat that really hits home as to how disastrous this transfer has been is he suffered more injuries than he scored goals.
It certainly didn’t help that the now-32-year-old arrived for the initial pre-season seven kilos overweight.
After failing to come to an agreement with a new club in the summer of 2023 after his £400,000-a-week deal with Madrid ran out, he announced his early retirement from football.