1. Mykhailo Mudryk – Chelsea – £88.5m
From Shakhtar Donetsk → To Chelsea
Chelsea’s acquisition of Mykhailo Mudryk in January 2023 for £88.5 million was a significant statement of intent. The Ukrainian winger was expected to inject pace and creativity into the squad. At Shakhtar his stock had risen so much due to Champions League displays, that Arsenal, Brentford and Chelsea were all linked. With Chelsea eventually winning his signature. He signed an 8 year deal on large wages so that the club could amortise his wages over the course of his contract. However, his tenure at Stamford Bridge has been fraught with challenges both on the field, and off it.
Initially, Mudryk struggled to adapt to the Premier League’s intensity, managing only a handful of assists and failing to score in his first season. Critics pointed to his lack of physicality and decision-making as key factors in his underwhelming performances. Despite flashes of his potential, consistency remained elusive. His pace would get him into positions, but then he would fluff chances or make poor decisions when he got into the more advanced spots.
The situation worsened in December 2024 when Mudryk was provisionally suspended after testing positive for meldonium, a banned substance. The test, conducted in October, revealed the presence of the drug in his system. Mudryk has denied knowingly ingesting any prohibited substances and is cooperating with authorities to determine the cause of the adverse result.
If the B-sample confirms the initial findings, Mudryk could face a ban of up to four years, effectively sidelining him during his prime playing years. This development not only jeopardises his career but also represents a significant financial and reputational blow to Chelsea. The club, already under scrutiny for its transfer expenditures, may have to reassess its investment strategies and player support systems.
In light of these events, Mudryk’s transfer has to be viewed as the most ill-fated in Premier League history. The combination of a hefty transfer fee, lacklustre performances, 8 year contract and potential long-term suspension all tallies up to the worst signing in Premier League history.
2. Romelu Lukaku – Chelsea – £97.5m
From Inter Milan → To Chelsea
Romelu Lukaku’s £97.5m return to Chelsea in the summer of 2021 was meant to be the fairytale comeback of a striker who had matured into one of Europe’s best. After leading Inter Milan to a Serie A title with 64 goals in 95 appearances, Chelsea believed Lukaku would solve their long-standing issues up front. Instead, it turned into one of the costliest disasters in Premier League history.
Lukaku started his second spell brightly, scoring four goals in his first four games, but things quickly went south. Struggling to fit into Thomas Tuchel’s system, he often appeared isolated, ineffective, and uncomfortable with the tactical demands placed on him. His infamous struggles with his first touch returned, making him a liability in possession. Despite being signed to provide a consistent goal-scoring threat, he managed just eight league goals in 26 appearances, far below expectations for a player of his calibre.
Off-field controversy further derailed Lukaku’s time at Chelsea. In December 2021, he gave an unauthorised interview to Sky Italia in which he criticised Tuchel’s tactics and expressed a desire to return to Inter Milan. This bombshell caused a major fallout between Lukaku, Tuchel, and the club’s hierarchy, leading to his temporary exclusion from the squad. Though he apologised, the damage was done—both his relationship with the fans and his confidence on the pitch were shattered.
By the end of the 2021/22 season, Chelsea were desperate to move him on. Lukaku was loaned back to Inter Milan in the summer of 2022, just a year after his record-breaking arrival. However, Inter didn’t pursue a permanent transfer, and in 2023, Chelsea loaned him out once again—this time to Roma. After multiple underwhelming loan spells and mounting wage costs, Chelsea finally managed to sell Lukaku in the summer of 2024 to Napoli for €30m, representing a staggering financial loss on their original investment.
Lukaku’s second stint at Chelsea stands as a prime example of poor planning, inflated fees, and a complete breakdown in player-club relations. What began as a marquee signing ended in disappointment, off-field drama, and a massive financial hit for Chelsea, cementing Lukaku’s place as one of the worst Premier League signings of all time.
3. Antony – Manchester United – £85m
From Ajax → To Manchester United
When Manchester United signed Antony in the summer of 2022 for £85m, it marked the second-highest transfer fee in the club’s history. The Brazilian winger was brought in by Erik ten Hag, who had coached him at Ajax, with hopes that he would bring flair, creativity, and goals to United’s attack. However, Antony’s time at Old Trafford has been marked more by inconsistency and frustration than brilliance.
The massive fee raised expectations that Antony has struggled to meet. While he’s shown flashes of his technical ability and scored some spectacular goals, his overall output has been underwhelming. Critics have also pointed out his predictable style of play. Antony is heavily reliant on his left foot and often cuts inside, making him easier for defenders to neutralise. His decision-making in the final third has also been questioned, with numerous wasted opportunities and misplaced passes. Additionally, Antony’s showboating—such as spinning tricks with no clear purpose—has drawn criticism, especially when it hasn’t been accompanied by effective end product.
Beyond his on-pitch struggles, Antony has faced controversy off the field. Allegations of misconduct have surfaced, creating further distractions and tarnishing his reputation. While these matters are still under investigation, they’ve added another layer of scrutiny to a player already under immense pressure to justify his price tag.
Antony still has time to improve and prove his doubters wrong. However, for now, his transfer fee looms large, and his performances haven’t come close to justifying United’s eye-watering investment and he barely gets minutes on the pitch to turn it around. With a move away from Man United looking likely after Ruben Amorim has replaced Erik ten Hag, the likelihood is that he will not be able to justify the fee paid for him.
4. Jean-Kévin Augustin – Leeds United – £18.4m
From RB Leipzig → To Leeds United
Leeds United’s signing of Jean-Kévin Augustin in January 2020 seemed like a bold move at the time. The French striker, once a hot prospect at Paris Saint-Germain and RB Leipzig, had fallen out of favour in Germany but was still seen as a player with untapped potential. Leeds, fighting for promotion to the Premier League under Marcelo Bielsa, brought him in on a loan deal with an obligation to buy if they secured promotion.
However, the move turned into a nightmare almost immediately. Augustin struggled with fitness from the outset and played just 48 minutes across three substitute appearances. Bielsa’s demanding style and intense training regime appeared to be too much for a player who hadn’t played regularly in months. With recurring muscle injuries, Augustin never got up to speed, and Leeds ultimately chose not to retain him once their promotion was sealed.
The real disaster came after Augustin left. Due to a contractual clause, Leeds were legally bound to pay RB Leipzig £18.4m, even though the player never featured for them in the Premier League. Leeds contested the payment, claiming the obligation was void because the season was extended due to the COVID-19 pandemic. After a lengthy legal battle, FIFA ruled in Leipzig’s favour, forcing Leeds to pay the fee for a player who contributed next to nothing.
In the end, Augustin’s time at Leeds became one of the strangest and most costly sagas in recent football history. Despite barely kicking a ball, he ended up costing the club millions, making this one of the worst deals not just in Premier League history, but football history.
5. Adrián Mutu – Chelsea – £15.8m
From Parma → To Chelsea
Adrián Mutu’s move to Chelsea in 2003 had all the makings of a success story. The Romanian forward was coming off a stellar season at Parma, where he scored 18 goals in Serie A. Signed for £15.8m during Roman Abramovich’s first summer of spending, Mutu was part of an exciting new era at Stamford Bridge. He made an immediate impact, scoring four goals in his first three games and quickly becoming a fan favourite.
However, Mutu’s bright start didn’t last. His form dipped during the second half of the season, and rumours began to surface about problems off the pitch. When José Mourinho replaced Claudio Ranieri as Chelsea’s manager in 2004, Mutu found himself on the fringes. His relationship with Mourinho soured quickly, culminating in a public falling out.
The situation reached a breaking point in October 2004 when Mutu tested positive for cocaine. Chelsea terminated his contract immediately, citing gross misconduct. To make matters worse, FIFA ordered Mutu to pay Chelsea £14.6m in damages, an amount that led to years of legal wrangling. Mutu later admitted he turned to drugs due to personal struggles and the pressure of living up to expectations.
For Chelsea, Mutu’s signing represented a significant financial and reputational loss. He played just 27 games and scored 10 goals for the club, a meagre return on a substantial investment. Despite his talent, his off-field issues overshadowed everything he did on the pitch, making him one of the Premier League’s most infamous signings.
Even after leaving Chelsea, the saga continued. Mutu rebuilt his career in Italy, thriving at Fiorentina, but the damage to Chelsea was already done. The legal battles over the damages dragged on for over a decade, cementing Mutu’s place among the worst signings in the club’s history.