Tue 12 April 2022 | 7:30

Biggest Premier League Transfer Flops

Join us as we take a look at some of the biggest Premier League transfer flops

The Premier League clubs have always had a hand in some of the biggest transfers that are happening around the Europe. As perhaps the most competitive league in Europe, these EPL clubs must ensure that their every resource is spent towards beating their competition and in football this usually means buying better players. And if there is one certainty in this sport, it is that good players and managers do not come cheap.

We have previously delved into such matters and EPL’s record transfers but we’re here to take a different approach this time as we are going to look at some of the big money signings in the Premier League to figure out who are the

biggest Premier League transfer flops of all time

. Of course, a transfer being deemed a flop is a subjective term as fans, players and managers always debate whether a player has performed the way that was expected of him and if he is a flop or not. For our part, we have tried to bring up facts and numbers backing our claim of who has been a flop or not. Let’s find out:

Biggest flops in Premier League History

Of course, when there is talk of transfers, usually the newer a transfer, the more expensive it is, so we have decided to not only judge these by the transfer fee but also the player’s wages as well as the period they were signed in and what was expected of them. So, without further ado, here are the biggest flops in Premier League history:

Alexis Sanchez (Arsenal to Manchester United)

The only reason that Alexis Sanchez’ name is not on top of the list of the

biggest flops in football history

is his relatively small transfer fee that was just a technicality behind what was really happening which was him being swapped for Henrikh Mkhitaryan to join Manchester United with Mkhitaryan going the other way to Arsenal. Sanchez’ fall from grace, his horrendous performances with Manchester United and his astronomical salary are all part of why he is considered to be one of the biggest Premier League transfer flops.

Sanchez who started his career at Cobreola in Chile, made a name for himself after joining Udinese in 2006. Following several loan spells, Sanchez started to show his mettle in the Serie A and therefore caught the attention of Barcelona who signed him in 2011. His three seasons at Barca yielded a total of 5 trophies but Barca was ready to move the Chilean on. Which was where Arsenal came in. a perfect match for Wenger’s


, Sanchez teamed up with Ozil and often Giroud to deliver magnificent performances for the Gunners as he became one of the best Premier League players during his 3 and half seasons with the Gunners.

Sanchez’ last full season at Arsenal saw him score 24 in the Premier League and 30 overall, but he was about to go to his final season with at Arsenal without extending his contract. Almost every big club in Europe was trying to sign him but United finally managed to outdo Manchester City and signed Sanchez on a half million pound per week salary. Where Sanchez had scored 80 goals for Arsenal in 166 matches, he went on to score only 5 for United over the course of 45 matches.

His disappointing form as well as his huge salary prompted United to loan Sanchez to

Inter Milan

in 2019 and he has been there ever since, after United released him on the end of his 1-year loan and he signed for Inter on a free. To become one of the best player in the Premier League in the past decade only to fall from grace this hard on such a short time certainly deserves the title of being one of the biggest Premier League transfer flops.

Andriy Shevchenko (AC Milan to Chelsea)

The only Ballon d’Or winner on our list of biggest Premier League transfer flops is the AC Milan legend Andriy Shevchenko who is still to this day remembered as being one of the greatest European strikers of all time as well as being one of the best AC Milan players in the history of the club. Shevchenko became the third Ukrainian player to ever win the Ballon d’Or, when he did so in 2004 over rivals such as Thierry Henry, Ronaldinho and Deco, but even he was not immune from making bad transfer decisions.

After spending 7 seasons with AC Milan and becoming their 2nd best goal scorer of all time as well as helping the Rossoneri win a Serie A title, a Coppa Italia trophy and the 2002-03 Champions League title, Andriy Shevchenko was looking for a new challenge following the 2006 World Cup. He decided to join Chelsea who were only acquired by Roman Abramovic a couple of years earlier and were great admirers of Shevchenko. Milan was reluctant to sell Shevchenko but agreed to do so after the English club offered £30.8 million which broke the Premier League transfer record.

Sheva joined Chelsea at the start of the 2006-07 season but unlike AC Milan where the whole team was set up in a way that helped him, at Chelsea he was just another player in a line of European superstars that the club was buying. Mourinho’s defensive football didn’t help Shevchenko as well since he was asked to defend a lot more than he was used to. Suffice it to say that Shevchenko didn’t at all gel with the Chelsea squad and although he did sporadically score goals, the injuries he suffered as well as Chelsea’ playing style kept him out of the first team for the most part,

After two seasons and 77 matches for Chelsea, Shevchenko had only scored 22 goals as a striker, which was a complete failure for a Ballon d’Or winner and the reason he is among the biggest flops in football history. Add to that fact his age (31) which prompted


to move him on after only two seasons, first to his old club

AC Milan

on a loan move, and after he failed to score any league goals there, back to Dynamo Kyiv where he finished his career at.

Fernando Torres (Liverpool to Chelsea)

Another former Chelsea player on the list of

soccer players that flopped

is the Spanish Fernando Torres who had a similar story to that of Alexis Sanchez where he went from hero to zero on a January transfer. The Spanish striker had become one of the best


players of the Premier League era and was one of the best players in the world during the 3 and half seasons he spent with the Reds but his transfer to Chelsea in the January of 2011, resulted in him experiencing a severe drop of form and decline.

Torres, whose career started at

Atletico Madrid

and made his debut for them in the Segunda Division, had become one of the most coveted young talents around Europe by 2007. At which point he was signed by Liverpool in a deal worth £20 million which saw Luis Garcia also go the other way to Atletico. Torres then went on to become one of the best strikers in Europe between 2007 and 2011, becoming the fastest Liverpool player to reach 50 goals for the club, a record that has since been broken by Mohamad Salah.

Just as Liverpool were gearing up to be title contenders again, Torres decided to give the green lights to Chelsea to sign him which resulted in British transfer record of £50 million that also made Torres the most expensive Spanish player of that time. Obviously, the expectations were quite high from Torres but he failed to deliver on any of those expectations. his first 6 months saw him only score once for the Blues.

The rest wasn’t that much better, although he did manage to score quite a few times but he was only a shadow of his former self. He did however help Chelsea win two major European trophies which makes his story a bit more successful than most of the players on this list of biggest Premier League transfer flops. Torres spent the last 3 seasons of his contract at Chelsea on loan at AC Milan and later Atletico and finally signed for Atletico in 2016. He retired from football in 2019 at Japan’s Sagan Tosu.

Alvaro Morata (Real Madrid to Chelsea)

Alvaro Morata is a good striker, not a great one, but one that could do very well supporting a much more prolific striker. But throughout his career, Morata’s skills as a striker has always been overestimated by different clubs which has resulted in him being the subject of several high-profile transfers, couple of which could be considered as transfer flops. The difference between Morata and the soccer players that flopped is that he always finds a way to bounce back, evidenced by his relatively good form at Juventus.

For anyone that has been following the Chelsea football club in the past two decades, it is common knowledge that Chelsea likes to overpay when they are buying strikers, this has resulted in several flops, 4 of which are among the

biggest flops in Premier League history

, and Alvaro Morata is one of them. The Spanish striker who started his career at Real Madrid later found prominence at Juventus and after a season back at Real Madrid caught the eye of Chelsea who were looking for a prolific goal scorer.

The fact is that Morata was never a prolific goalscorer something that Chelsea should’ve known looking at his prior record but they still decided to pay somewhere around £60 million for him. What followed was something like a Fernando Torres situation, where Morata would miss open goals and sitters and be jeered at by fans for not scoring enough goals.

The expectations that were set for him even before he arrived was not at all what he was capable of or was in fact the style that he played and he ended up being one of the biggest Premier League transfer flops. Although he has since bounced back in his time at Atletico Madrid and



Angel Di Maria (Real Madrid to Manchester United)

A player that has had more of a happy ending than the rest of this list would be the Argentine Angel Di Maria whose transfer from

Real Madrid

to Manchester United in 2014 broke British transfer records but his one season stay at Manchester United ended up being a horrible mistake which makes his transfer one of the biggest flops in football history. Fortunately for Di Maria, he went on to join


and became an important figure in them dominating the Ligue 1.

 After starting his career at Rosario Central, Angel Di Maria found his way to Benfica which is a club that is a bit of a talent factory. At


, Di Maria honed his skills and got a dream move to Real Madrid where he became part of a Los Blancos generation that would bring back European Glory to Bernabeu. Di Maria helped Madrid win a La Liga title and the Champions League on his final season with them before transferring to Manchester United for a price reported to be around £59.7 million which broke Premier League record at the time.

Di Maria was in fact part of a wave of expensive players that Manchester United started to sign after Sir Alex Ferguson’s departure from the club. A policy that for the most part hasn’t worked for them since so many of those players are on this list. Di Maria’s time at United was during the time of Louis van Gaal as United’s manager and injuries as well as his bad run of form, particularly near the end of the season, made it so that many deemed him as one of the biggest Premier League transfer flops.

In hindsight, he deserved that title, not because he is or was a bad player but because the transfer was not a great fit for either party and both have benefited Di Maria’s departure at the end of his nightmarish season at United.

Nicolas Pepe (OSC Lille to Arsenal)

The next player on our list of biggest Premier League transfer flops is a rather recent one and that is Arsenal winger, Nicolas Pepe, who shattered Arsenal’s transfer records to move to the club in 2019. The Ivorian winger came with a lo of expectation in a bidding war that involved both Arsenal and Liverpool but besides a few sparks here and there, has failed to failed to deliver on the expectations that were set for him. The fact that he is still Arsenal’s record transfer makes those expectation even bigger and adds to the fact that he is deemed a flop by so many.

Despite being Ivorian, Nicolas Pepe was born in France. He started his career in France’s lower leagues and gained prominence when he joined Angers. After being promoted with Angers and experiencing Ligue 1 for a season, Pepe joined the up and coming


who excel at developing young talent. And they did so in Pepe’s case as well as he tore though Ligue 1 defenders in his two seasons at Lille. His final season at Lille saw him score 22 goals in the league which then prompted Arsenal to pay big money for him.

After a summer of speculation, Pepe arrived at Arsenal in a £72 million that became subject of a controversy later on. But as far as his performances go, it didn’t help that Arsenal was having a bit of an identity crisis when he arrived. A crisis that has only been recently sorted to a degree but unfortunately for Pepe, it seems that he is no longer in Arteta’s plans. His second season at Arsenal was much more of a success than his first and now 3rd season as he scored 16 goals in all competitions but when looking at his whole time at Arsenal, his transfer has been one of the biggest Premier League transfer flops.

Kepa Arrizabalaga (Athletic Bilbao to Chelsea)

We witnessed some of the best goalkeepers of all time in the last two decades, the likes of Gigi Buffon, Oliver Kahn and Iker Casillas but the title of the most expensive goalkeeper of all time doesn’t belong to any of them. It belongs to Chelsea’s Kepa Arrizabalaga who joined the Blues after the departure of Thibaut Courtois in 2018. The former


player started out ok but fell off hard in his second season and has now been replaced by Mendy in Chelsea’s goal.

The circumstances surrounding Kepa’s arrival was strange since he was barely known even in La Liga circles, although he had decent experience and showed signs of great potential. But to go out of your way to pay a sum of £71.6 million for a relatively inexperienced goalkeeper is just asking for pressure to be piled up on such a young player.

Whether it was that immense pressure that he felt because of his price tag or the way he was coached, Kepa ended up failing to impress the Chelsea staff, whether it was Mauricio Sarri, Frank Lampard or Thomas Tuchel at the helm. Certainly, one of the biggest flops in football history, Kepa Arrizabalaga has still a lot to play for since he is only 27. Perhaps a move back to La Liga would do him well.

Harry Maguire (Leicester City to Manchester United)

We don’t think there is even need for us to elaborate why we put Harry Maguire on this list since his recent failures both as a defender and a captain is common knowledge to any football fan. What we will elaborate on is the pattern that is seen here a lot and that is undue expectations from players simply because of their price tag which leads to a lot of soccer players that flopped and Maguire is no exception to that.

There is no doubt that Harry Maguire could do decent defending when he is in the right setup as his performances at

Leicester City

and England have somewhat confirm that but what is mind boggling is putting him in charge of a weak defensive line at Manchester United, perhaps a role he is not comfortable with, as well as making him a captain of such a big club. Add to that his massive price tag of £80 million which makes him the most expensive defender in history and you end up with a lot of negative pressure on a player that already had a mountain to climb.

Harry Maguire simply wasn’t the player that Manchester United were looking for. He wasn’t partnered with a player that could cover his weaknesses and he himself didn’t get better overtime which is why he is considered to be one of the

biggest Premier League transfer flops


Paul Pogba (Juventus to Manchester United)

Another Manchester United player on our list is Paul Pogba. The World Cup winner hasn’t by any means bad during his time at Manchester United but his transfer, the expectations from his arrival and the fact that he is a completely different player when he plays for France has all contributed to the fact that many consider him to be one of the

biggest Premier League transfer flops


Paul Pogba was a product of Manchester United academy but due to lack of game time he decided to leave

Manchester United

on a free to join Juventus in 2012. He went on to become one of the best midfielders in the world which prompted his old club to pay £89.3 million to Juventus in 2016, making Pogba the most expensive player of all time. This is at the time where Ronaldo and Messi are at their full power and for a 23-year-old to be the most expensive player ever means that expectations from him was unnaturally high.

Although Pogba had the potential to fulfill those expectations, United’s turbulent period which continues to this day prevented him from doing so. He was simply not surrounded with good enough players in midfield and ever manager had his own idea of where to play him. Now at the end of his contract, after paying that sum for his transfer fee and twice over his wages in all these years, Paul Pogba is once again about to leave on a free which is further proof that his transfer was a flop!

Romelu Lukaku (Inter Milan to Chelsea)

Romelu Lukaku holds the record for having the highest transfer fees of all time with all of his 6 transfers combined. The Belgian striker’s services have been worth a whopping €325.56m ever since he left Anderlecht to join Chelsea in 2011. Over the years Lukaku has had to constantly prove himself but some of his transfers just didn’t work such as him moving to Manchester United or his recent transfer to his old club Chelsea which makes him one of the

Premier League flops of 2021/22


While the Belgian was never given the chance the first time around at Chelsea, Everton became the place where he honed his skills as a striker. Then came the Manchester United transfer which never suited him but Inter Milan became his saving grace as he helped the Nerrazzuri claim the scudetto once again. Which leads us to the transfer in question here. after scoring 64 times in 95 games for Inter and winning the Serie A as well as Serie A MVP award, Lukaku decided to once again join Chelsea, stating that he had “unfinished business” at the club.

And so Romelu Lukaku joined Chelsea once again for a transfer fee of £97.5 million. The transfer saga surrounding it and the way he left Inter brought down a lot of heat on Lukaku, not to mention unnecessary pressure which made things a lot harder for him. As it stands, his transfer has not worked at all in anyone’s favor since Chelsea’s manager Thomas Tuchel doesn’t really believe in him and Lukaku himself hasn’t been performing when he has been given the chance to. His transfer certainly counts Premier League flops of 2021/22. Whether he changes his fortunes in the future seasons or not remains to be seen!



source: SportMob

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