Worst Premier League Transfers of All Time

The world of football is filled with excitement and anticipation regarding new transfers. The signing of a player can bring hope and expectation to fans, and it can make or break a club’s season. However, not all transfers are successful. In fact, many high-profile transfers have failed to live up to their expectations, leaving fans and clubs disappointed. This article will delve into some of the worst Premier League transfers of all time, examining the transfer fees, the hype, and ultimately the reasons behind their lack of success.

From Alberto Aquilani to Fernando Torres, these transfers serve as a cautionary tale for clubs and fans, highlighting the importance of careful consideration and due diligence when investing in new talent.

As we may know, the Premier League is the richest in the world and, within it, has some of the richest clubs to date.

In recent years we have seen the total spending spree beaten, with even the smaller clubs spending extortionate fees on players.

Clubs are willing to throw money away on an exciting prospect but unproven and sometimes not even heard of. They are in the middle of a season on ‘Football Manager’ and have come across this player with outstanding attributes no matter what position.

Struggles in the Premier League

Bringing in a player who doesn’t mix with the big-time can be very devastating. It can cost the club financially and blow their chance of trophies.

You have to remember that players are human beings as well and can be homesick and therefore just don’t fit in with the team or their style is very different from others and that doesn’t fit in with the team. They just don’t seem to adjust.

The game in England is tough and fast-paced, especially for strikers who seem to struggle due to the hard-hitting centre-backs in the Premier League.

Whoever your club has bought from Europe, worldwide, or even across leagues in England, it’s hard to adapt, and sometimes it just doesn’t work out.

It’s just the luck of the draw in some cases.

It’s not an easy adjustment

Some players just fit in when they come from abroad or even from the lower leagues, they seem to have no problem with the physical and high tempo of the game. Their style of play suits them from the off.

If a player fails, then it’s just on to the next one. The problem is fans and the managers, and even the club look for instant success, and we all know that doesn’t happen overnight.

Detailed List Of 27 Worst Premier League Transfers of All Time

Here, we look at some transfers in the premier league that in my opinion, have been the worst purchases in no particular order.

1. Helder Postiga | Porto – Tottenham | £8.5 million | 2003

Postiga had been impressive in Portugal, having scored 33 goals in 70 appearances for Porto, as well as helping his country win the UEFA European Under-21 Championship in 2002

The young striker was influential in Jose Mourinho’s Porto side that won the UEFA Cup, but in 2003/04 when he signed for Spurs, it just didn’t work out.

Tottenham shipped him back to the Portuguese giants in exchange for Pedro Mendes, and he was actually better on Football Manager!

Postiga had a horrible season, but at least he scored one goal in the Premier League.

2. Michael Owen | Real Madrid to Newcastle | £16.8 million | 2005

He was such a talented player who lit up the world with his club performance at Liverpool and the 1998 World Cup, his stunning goal against Argentina. His move to Real Madrid was just as bad with ten goals off the bench. Signing for Newcastle just didn’t work out for him where he was bombarded with injuries.

He started his career at 16 and scored on his debut for Liverpool in their 2-1 defeat to Wimbledon at Selhurst Park. His body started to break down in his 20s.

3. Christian Benteke | Aston Villa – Liverpool | £32.5 million | 2015

Signed as a replacement for Luis Suarez, fans know Benteke for his creative and offensive style of play and his formidable presence in the box, which he was capable of quality finishing, which we saw at Aston Villa. He used to score some beautiful goals for Villa, but his style of football just didn’t suit Liverpool; in fact, it stuck out like a sore thumb!

His move to Crystal Palace didn’t work out there either, and he just fizzled away, which is a shame because he was a great player.

4. Gilberto | Hertha Berlin – Tottenham Hotspurs | £2.5 million | 2008

Tottenham Hotspur signed Brazilian midfielder Gilberto from Hertha Berlin for an undisclosed fee. But according to reports, Gilberto was signed by Tottenham Hotspur from Hertha Berlin for a fee in the region of £2.5 million.

Struggled immensely during his time at Spurs and only made ten appearances, being substituted the three of them at halftime. Unfortunately, he had a terrible debut at White Hart Lane, which was a sign of things to come after losing the ties against PSV Eindhoven in the UEFA Cup.

Some South Americans do tend to struggle to adapt to the premier league.

5. Fernando Torres | Liverpool to Chelsea | £50 million | 2011

Chelsea signed Spanish striker Fernando Torres from Liverpool for a British transfer record fee of £50 million. Torres had been one of the best strikers in the Premier League, but his form had dipped prior to the move to Chelsea.

A hard-working striker known for the ability to find himself in goal-scoring positions using his pace and vision to get in behind defenders. He was world-class in my book.

Despite high expectations, Torres struggled to adapt to Chelsea’s style of play and found it difficult to replicate his previous form.

Torres scored just 20 goals in 110 appearances for the club throughout three and a half seasons, and his transfer to Chelsea is a complete disappointment.

Torres was just not consistent enough on the ball and he failed to adapt more quickly. His performance at Chelsea just went downhill.

6. Alexis Sanchez | Arsenal – Manchester United | Swap deal | 2018

He was a terrible signing, I think, he was amazing at Arsenal, and then joining the red devils, he only netted three goals. The first came from a penalty that he missed and scored the rebound!?!

As the saying goes, a workman always blames his tools which is what he did, blaming his teammates for the quality of the passing.

He was much loved by the fans at Arsenal and was one of the best premier league strikers, but he left Manchester United as a failure.

7. Paul Pogba | Juventus to Manchester United | £89 million | 2016

Man Utd let Pogba depart the club in 2012 on a free transfer to Juventus and bought him back for 89 million.

He was such a talented player for Juventus, but his return to Old Trafford didn’t work out. Pogba was a decent player and read the game well, and had so much power, but unfortunately wasn’t the player he was at Juventus.

Since his contract ran out, he returned to his former club on a free transfer. It was like deja vu.

8. Andy Carroll | Newcastle to Liverpool | £35 million | 2011

I don’t think he wanted to leave Newcastle at the time, it was his boyhood club, and he struck up a great friendship with Kevin Nalan at the time. A talented target man, but he just didn’t fit in with the Liverpool style of play, and he struggled to find form.

Knee injuries also disrupted him in his first full season and eventually, after a change of manager from Kenny Dalglish to Brenden Rodgers, he was soon loaned out to West Ham, who eventually signed him. But even there, he struggled to claw back to what he once was.

9. Danny Drinkwater | Leicester to Chelsea | £35 million | 2017

The Foxes had just won the league the previous year, and his move to Chelsea became a nightmare. He signed a five-year contract with the club, which was wasted because he featured just 12 times for the club, scoring one goal.

Drinkwater won the Premier League with Leicester the previous year and was a pivotal fixture in that squad.

His career at Chelsea lacked game time due to injuries.

10. Andriy Shevchenko | AC Milan to Chelsea | £30 million | 2006

He came to Chelsea with a glowing reputation. In his seven years at AC Milan, he was on form in front of goal, scoring 127 goals. Unfortunately, at Stamford Bridge, he struggled to adapt to the pace of the premier league.

The pace of the game in Italy is so much different from here in England and to the premier league, which is one of the reasons he did not succeed at Stamford Bridge. However, he scored some great goals for the club, including his wonder strike against Tottenham in 2007.

Since he left Chelsea, though, he never rediscovered his form.

11. Agustin Delgado | Necaxa to Southampton | £3.5 million | 2001

After arriving from Mexican football with a romping reputation for being a ruthless striker, his three-year stint at the Saints didn’t go down well.

I can remember then-manager Gordon Strachan saying that his expired yoghurt at home in his fridge was a bigger priority!

To be fair to him, he did arrive needing knee surgery which plagued him at St. Mary’s

12. Mario Balotelli | Milan to Liverpool | £16 million | 2014

A panic buys from Liverpool signing the former Manchester City striker that would either work out badly or well. His lack of effort on the pitch, even his behaviour off the pitch, was uninspiring.

The formation by manager Brenden Rodger at the time did not suit Balotteli’s characteristics.

I think the media overshadowed his time in England.

13. Jack Rodwell | Everton – Manchester City | £11 million | 2014

Another bright young prospect from Goodison Park moving to Man City was a terrible career move. His lack of form and injury problems led the coach to drop him from the team and eventually loaned out to Sunderland.

He was such a talented player, but his move to ‘the Etihad was a mistake in the making.

14. Juan Sebastian Veron | Manchester United – Chelsea | £15 million | 2003

After showing glimpses of his obvious class at Manchester United, which didn’t go quite to plan, he failed to produce it at Chelsea and just did not fit into their system.

Unfortunately, he didn’t meet the requirements of then-manager Jose Mourinho of a robust and physical presence in the middle of the park to control and dictate play.

15. Ali Dia | Southampton | FREE | 1996

Ali Dia’s transfer to Southampton is considered one of the worst transfers in Premier League history.

In 1996, he was signed based on false claims that he was a cousin of George Weah and a skilled footballer who had played for PSG, Brest, and Senegal. He made a disastrous debut and was revealed to be a semi-professional player who had been playing for non-league club Blyth Spartans.

Ali Dia was released from his contract and never played for a professional club again.

This transfer is a cautionary tale about the dangers of relying on agents and the importance of thorough scouting and due diligence before signing a player.

16. Alberto Aquilani | Roma to Liverpool | £20 million | 2009

In August 2009, Liverpool signed midfielder Alberto Aquilani from AS Roma for a reported fee of £20 million.

Despite high expectations, Aquilani struggled with injuries during his time at Liverpool and failed to live up to expectations.

Over two seasons, the Italian international made only 28 appearances and scored two goals.

Liverpool eventually loaned him to Juventus and sold him to Fiorentina in August 2012.

(You may read more on how many Premier League matches are played in a season.)

17. Massimo Taibi | Venezia to Manchester United | £4.5 million | 1999

Massimo Taibi, a goalkeeper, was signed by Manchester United from Venezia in August 1999 for a reported fee of £4.5 million.

Despite making four appearances for the club, he became infamous for several high-profile errors, including a howler against Southampton, leading to his nickname “The Blind Venetian”.

Consequently, Manchester United quickly sold to Reggina in January 2000, and his transfer to Manchester United is one of the worst Premier League transfers of all time.

18. Bebe | Vitoria de Guimaraesto Manchester United | £7.4 million | 2010

Bebe, a forward, was transferred to Manchester United from Vitoria de Guimaraes in August 2010 for a reported fee of £7.4 million.

Before his transfer, Bebe was a relative unknown, having played for several lower-league Portuguese clubs.

However, he had been recommended to Manchester United’s then-manager Sir Alex Ferguson by his assistant Carlos Queiroz, who had previously worked with Bebe at the Estrela da Amadora youth academy.

Despite high expectations, Bebe failed to impress at Manchester United, making only seven appearances and scoring two goals. Manchester United eventually loaned Bebe out to several other clubs before being sold to Benfica in 2014.

19. Jo | CSKA Moscow to Manchester City | £19 million | 2011

In July 2008, Manchester City signed Brazilian striker Jo from CSKA Moscow for a then-club record fee of £19 million.

Jo was one of the best strikers in Europe at the time, having scored 44 goals in 77 appearances for CSKA Moscow.

However, he failed to live up to the hype at Manchester City, scoring only six goals in 41 appearances. City loaned him out to Everton the following season and eventually sold him to Internacional in 2011.

Jo’s transfer to Manchester City is one of the club’s worst.

Nonetheless, find out the best ever Man City best players.

20. Winston Bogarde | Barcelona To Chelsea | FREE | 2000

In the year 2000, Dutch defender Winston Bogarde joined Chelsea on a free transfer from Barcelona.

At the time, he was 29 years old and had won two Champions League titles with Ajax and Barcelona.

However, his time at Chelsea was a disaster.

Despite being on a reported £40,000-a-week salary, Bogarde made only nine appearances over four years, refusing to leave the club despite being told he was not in the manager’s plans.

Borgarde’s stubbornness led to him being labelled a “mercenary”, and he became infamous for his lack of playing time and high wages. His move to Chelsea is one of the Premier League’s worst transfers of all time.

21. Kleberson | Atletico Paranaense to Manchester United | £6.5 million | 2003

In August 2003, Manchester United signed Brazilian midfielder Kleberson from Atletico Paranaense for a reported fee of £6.5 million.

Kleberson was a rising star in Brazilian football at the time, having helped his country win the 2002 World Cup. However, he failed to establish himself at Manchester United, making only 20 appearances in two seasons and struggling with injuries.

Despite being part of a star-studded Brazil team, Kleberson’s transfer to Manchester United is one of the club’s worst in recent memory.

On another note, find out why Manchester United chose Erik ten Hag over Pochettino.

22. Sergei Rebrov | Dynamo Kyiv to Tottenham Hotspur | £11 million | 2000

In 2000, Tottenham Hotspur signed Ukrainian striker Sergei Rebrov from Dynamo Kyiv for a club-record fee of £11 million.

At the time, Rebrov was one of the best strikers in Europe, having scored 73 goals in 146 appearances for Dynamo Kyiv.

However, he failed to replicate his form at Tottenham Hotspur, scoring only 10 goals in 60 appearances.

Rebrov’s lack of impact on the pitch and high transfer fee makes his move to Tottenham Hotspur one of the transfers of all time in the Premier League worst in recent memory.

23. Steve Marlet | Lyon to Fulham | £11.5 million | 2001

In August 2001, 27-year-old French striker Steve Marlet made a big-money move to Fulham from Lyon for a club-record fee of £11.5 million.

Marlet was highly regarded in France then, having scored 17 goals in 24 appearances for Lyon the previous season.

However, his time at Fulham disappointed him, as he only scored 11 goals in 54 appearances. Marlet’s transfer fee and lack of impact on the pitch make his transfer to Fulham one of the worst in the club’s history.

24. Francis Jeffers | Everton to Arsenal | £10 million | 2001

In 2001, English striker Francis Jeffers made a £10 million move from Everton to Arsenal, becoming the most expensive teenage footballer in British history at the time.

Jeffers had been highly regarded as a youth prospect and had scored 20 goals in 60 appearances for Everton.

However, injuries and lack of form hindered his time at Arsenal. He scored just four goals in 22 appearances before Arsenal loaned him out to several clubs.

Jeffers’ transfer to Arsenal is one of the club’s worst signings in recent history.

25. Corrado Grabbi | Ternana to Blackburn | £6.75 million | 2001

In 2001, Italian striker Corrado Grabbi joined Blackburn Rovers from Ternana for a fee of £6.75 million, breaking the club’s transfer record at the time.

Grabbi had been impressive in Italy’s Serie B, scoring 22 goals in 32 appearances for Ternana.

However, his time at Blackburn Rovers was a disaster, as he struggled with injuries and form, scoring only one goal in 19 appearances.

Grabbi’s transfer to Blackburn Rovers is one of the worst in the club’s history.

26. Roque Santa Cruz | Blackburn to manchester City | £17.5 million | 2009

In 2009, Paraguayan striker Roque Santa Cruz signed for Manchester City from Blackburn Rovers for a fee of £17.5 million.

Santa Cruz had been impressive at Blackburn, scoring 29 goals in 70 appearances.

However, injuries and lack of form hindered his time at Manchester City, and he only managed to score four goals in 24 appearances in his first season.

City loaned Santa Cruz out to various clubs in the following seasons, and his transfer to Manchester City is a disappointment.

27. Mateja Kezman | PSV to Chelsea | £5 million | 2004

In 2004, Serbian striker Mateja Kezman signed for Chelsea from PSV Eindhoven for a fee of around £5 million. Kezman had been highly regarded in the Eredivisie, having scored 105 goals in 122 appearances for PSV Eindhoven.

However, his time at Chelsea was underwhelming, as he struggled to adapt to the Premier League and the physical demands of English football.

Kezman only managed to score seven goals in 41 appearances for Chelsea, and Chelsea eventually sold to Atletico Madrid after just one season.

Kezman’s transfer to Chelsea is one of the worst in Premier League history.

Final Thoughts

the Worst Premier League Transfers of all time have left a lasting impression on fans and clubs alike.

The transfers we discussed in this conversation remind us that signing a player for a large fee or based on past performance does not always guarantee success.

While some players may struggle to adapt to a new environment or style of play, others may succumb to injuries or other personal issues.

These transfers highlight the importance of careful consideration and due diligence when investing in new talent and provide valuable lessons for football clubs moving forward.

Further Reading: