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The most expensive flops in Premier League history
(Image via https://twitter.com/oilysailor)
Despite being widely regarded as the best league around, the Premier League and its cohort of clubs don’t always get things right. Teams throughout the world of football are regularly exposed for their mismanagement, from poor training facilities and nutritional advice to players to failed managerial appointments and player signings that don’t quite live up to the hype. The latter scenario, where clubs don’t always recruit well, has occurred a frankly disturbing amount of times in England’s top flight.
Given the vast sums of money that English clubs have at their disposal in recent times, getting a signing wrong tends to receive more attention than it used to. Of course, it’s all relative, and English clubs have made shoddy acquisitions for decades, but it tends to become more of a talking point in the modern environment due to some of the extortionate fees that clubs in the Premier League are paying.
Some new additions are clearly panic buys, while others are a genuine attempt to close the gap on a club’s nearest rivals. There have been some standout signings that have looked worse as the season has progressed, though, with some professionals turning out for the biggest sides in the division. We aren’t just talking about Eric Djemba-Djemba and Ricky van Wolfswinkel here either, but a selection of other flops that failed to deliver despite promising so much.
So, without further ado, let’s take a look at some other notable signings that didn’t quite do it in the Premier League despite the clubs in question investing a great deal of money into acquiring their services.
Andriy Shevchenko’s time at Chelsea was a disaster
When looking back at some of the best strikers to have graced the beautiful game in the last 20 years or so, Andriy Shevchenko’s right up there for many people. A player who recorded notable success at AC Milan and scored screamers for fun, the Ukrainian is a legend at the Italian giants. As such, it made a lot of sense when Chelsea decided to splash the cash and bring him to the club in 2006. Spending £39.5 million in the process, Roman Abramovich got his man, and excitement around the 29-year-old’s move to the Blues was understandable. Soon, though, it became clear that Shevchenko was a player on the way down, with injuries getting in the way and inconsistent performances leaving him largely out of favor in the end. Signed as a world-class talent who would lead the line for Chelsea for a good few years, Jose Mourinho ended up sticking with Didier Drogba in the end, leaving the former Dynamo Kyiv star playing out of position before he eventually went back on loan to his beloved Milan, putting an end to his nightmare spell in London.
Paul Pogba’s failed move back to Manchester United can’t be ignored
(Image via https://twitter.com/The6thdisciple)
Judging by his decision to refuse to pull out all the stops to halt Paul Pogba’s move to Juventus in 2012, Sir Alex Ferguson clearly saw something he didn’t like about the Frenchman at the time, a player he branded disrespectful towards the Red Devils. Evidently, Ferguson was clearly right about the midfielder and his supposedly toxic behaviour. Recruitment since the Scotsman’s time as manager has been appalling overall, leaving fans dismayed at the lack of progress the club has made in the last few years. The scrutiny levelled at the Glazer family won’t go away; fans are boycotting matches and organizing regular protests, and you’ll struggle to find a supporter who is backing Manchester United for the Premier League title when it comes to football betting, and YouTube channels regularly focus on the mess that is always unfolding at the club. It’s perhaps best summed up by Paul Pogba’s return in 2016 for an astonishing then world-record transfer fee of £93.2m following his free transfer to Juventus just a few years previously. A flash in the pan, Pogba fell out with managers, his injury issues were never-ending, and he was viewed as a trouble-maker who lacked the hunger and desire to succeed at Manchester United. Given the huge amount of money the club invested in re-signing the World Cup winner, a lot more was expected of him. One of the biggest flops in Premier League history? Definitely.
A selection of honorable mentions
While Andriy Shevchenko and Paul Pogba have been the main focus here, they certainly aren’t alone. In fact, a number of horrifically expensive bad signings also deserve a mention. For starters, Danny Drinkwater’s move to Chelsea for a staggering £34.1 million in 2017 certainly didn’t go to plan, with the Premier League winner making just 12 Premier League appearances for the club in his debut season before being completely ignored afterward. Southampton’s £13.6 million investment in Dani Osvaldo in 2013 is another one that didn’t quite work out either, with the Roma man scoring just three goals in 855 Premier League minutes while also head-butting club favorite Jose Fonte in training.
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Some other notable failed investments by Premier League clubs include the likes of Ricky Alvarez (Sunderland), Bosko Balaban (Aston Villa), Serhiy Rebrov (Tottenham), Fernando Torres (Chelsea), Tomas Brolin (Leeds United), Adrian Mutu (Chelsea), Alexis Sanchez (Manchester United), David Bentley (Tottenham), Roger Johnson (Wolves), Bebe (Manchester United), Steve Marlet (Fulham), Alberto Aquilani (Liverpool), Giannelli Imbula (Stoke City), and Kostas Mitroglou (Fulham).
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Leon Bailey is a Jamaican professional football player who plays as a right winger for Serie A club Roma, on loan from Premier League club Aston Villa, and for the Jamaican national team and in this article, we will see more about the player’s Net Worth, Salary, Sponsors, Girlfriend, Tattoos, Cars, and more.
Leon Patrick Bailey famously called Leon Bailey joined Aston Villa from the German club Bayer Leverkusen in 2021. He is one of the top talents in Jamaica and has been playing at a top level in recent times. He works hard on the pitch and has high dreams of achieving a lot in the footballing world.
He has won the Belgian Young Footballer of the year in 2015 back in his times at Genk and later he moved to Leverkusen. He represents the Jamaican national football team since 2019 and has been playing regularly for the team. Let us get to know more about the winger’s profile in this article.
Leon Bailey’s Net Worth and Salary
Leon Bailey is a young player and footballing has contributed much to his earnings. The player’s net worth is estimated to be €17 million as of 2026. The market value of the player in 2026 is valued at €35.00m by Transfermarkt. He currently earns a whopping salary of 6 Million Euros per year playing for the club Roma. His salary at Serie A is higher than what he was earning for Aston Villa.
Leon Bailey Club Career
Leon began his youth career with Phoenix All-Stars. In 2015, Bailey joined the Belgian club Genk and quickly established himself as one of the top young talents in the league. He helped Genk win the Belgian Cup in 2016 and was named the league’s best young player in the same year.
Since joining Bayer Leverkusen in January 2017, Bailey has continued to impress with his performances on the field. In his first full season with the club, he scored 12 goals and provided 5 assists in all competitions. He also helped Leverkusen reach the final of the DFB-Pokal.
In the 2018-2019 season, Bailey was the club’s top scorer with 12 goals and 8 assists. He was also named in the Bundesliga Team of the Season. He continued his impressive form in the 2019-2020 season with 8 goals and 8 assists.
Bailey signed for Premier League club Aston Villa. He made his debut as a substitute on 14 August 2021 and scored his first goal for Villa on 18 September 2021 in a 3–0 home victory over Everton. His first season with Aston Villa was marked by several injuries which limited him to only 7 starts.
Leon Bailey International Career
Bailey made his debut for the Jamaica national team in 2016 and has since represented his country at several tournaments, including the CONCACAF Gold Cup and the Caribbean Cup. In May 2019, Bailey was named to the Jamaican provisional squad for the 2019 CONCACAF Gold Cup and officially announced that he would represent the Reggae Boyz.
He earned his first cap in June 2019 and scored his first goal for Jamaica in September 2019 in a CONCACAF Nations League match. It’s also noted that Bailey was eligible to represent England but he has no grandparents born in England. He moved to the Aston Villa club in 2021 and was a top performer for the club. Leon Bailey moved to the Serie A club Roma in 2025 on loan. Reports indicate he will join Roma permanently after the season.
Leon Bailey Family
Leon Bailey was born on 9 August 1997 in Kingston, Jamaica. His father’s name is Craig Butler, and his mother’s name is not known but they struggled a lot to make him reach professional-level football. The other details of the family are not revealed yet.
Leon Bailey’s Girlfriend
The Winger has been enjoying his relationship with Stephanie Hope. The couple has been a joyful pair. The couple is blessed with a baby boy who is still unnamed and The proud father loves to spend time with his young kid.
Leon Bailey Sponsors and Endorsements
Leon Bailey has not been seen endorsing any company on his social media accounts. The player is in his growing phase and will attract sponsors if he is able to show up his abilities and skills on the field.
Leon Bailey Cars and Tattoos
Leon Bailey has been spotted driving a Brabus Mercedes Benz in the streets of Kingston in Jamaica. It is certain that the player has a decent car collection in his garage to roam out. Like many footballers, Leon Bailey has inked his skin on both the left and right shoulders, hands, and on his chest.
Read More:
Consider yourself a fan of football? Many fans of fantasy football believe that they have a high level of knowledge of the sport, but this is not always proven to be true once the trivia questions commence. Whether you have watched football all of your life or you simply enjoy debating with other fans, football trivia is always a fun way to put your knowledge to the test. With this in mind, this post will provide the ultimate trivia challenge for football fans who believe they have what it takes. Read on to find out more.
Legends of the Game
First, let’s start with a few questions about legends of the game that every avid fan should know:
- Which player was the first to win the Ballon d’Or five times? A: Lionel Messi
- Which player is the all-time Premier League assist leader? A: Ryan Giggs
- Who scored the winning goal for France in the final of Euro 2000? : Zinidine Zidane
- Which striker from Brazil was known as “O Fenômeno”? A: Ronaldo
- Who was the top goal scorer in the first Premier League season? A: Teddy Sheringham
These questions should have gotten you warmed up, so let’s move on to the next section:
Fantasy Football Brain Teasers
Fans of fantasy football know the importance of data and statistics. Here are a few questions that will get your memory of stats from seasons gone by:
- Which player has scored the most FPL points in one season? A: Mohammed Salah (344 points in 2024/25)
- Which player was the top-scoring player in the first FPL season (2002/23)? A: Thierry Henry
- Who is the most expensive FPL player ever? A: Erling Haaland (£15 million in 2024/25)
- Who has the biggest individual game week score ever? A: Wayne Rooney (32 points in GW22 of the 2009/10 season
Moving on to the next round.
World Cup Trivia
The World Cup is an event every football fan looks forward to. Here are a few tough questions any avid fan should know:
- Which nation lifted the first FIFA World Cup in 1930? A: Uruguay
- Who is the most recent player to win the World Cup as a player and a manager? A: Didier Deschamps (player in 1998 and manager in 2018)
- Which player has scored the most goals in a single World Cup tournament? A: Just Fontaine with 13 goals for France in 1958.
Bonus Round
Football fans love nothing more than competition. This is why many also enjoy playing online slot games in their spare time. It is hard to beat the thrill and excitement of an immersive slot game with colourful visuals, slick animations, and satisfying sound effects. You can even enjoy free spins at some casinos, allowing you to play a range of slot games without having to spend your own money.
Hopefully, this trivia will have put your knowledge to the test and perhaps taught you a thing or two. Send it to your friends to see how their knowledge compares and who has the bragging rights.
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