It’s no secret that good transfer business can turn a solid season into a spectacular one, though there have been as many misses as there have been hits over the years. For every Mo Salah or Thierry Henry there’s been a Jack Rodwell or a Ricky Alvarez and we’ve picked out the five worst EPL transfers for you below.
Danny Drinkwater, Leicester City to Chelsea (£35m, September 2017)
Chelsea are frequent offenders in this article, beginning with their deadline day move to sign combative midfielder Danny Drinkwater from Leicester City in 2017.
The signing seemed logical on paper, as Drinkwater was a key part of the Leicester side that won the Premier League in 2016. The transfer reunited him with former Foxes teammate N’Golo Kante, too, as Chelsea aimed to win the title for the second year running under Antonio Conte.
Drinkwater commanded a hefty fee at £35 million, but he rarely proved to be a good fit for Chelsea, looking underwhelming for the majority of his 22 appearances in his first campaign for the club. A series of injury problems, disciplinary issues and mental health struggles followed as Drinkwater played just once more for the Blues in a five-year stay, having spells on loan at Aston Villa, Burnley, Reading and Turkish side Kasımpaşa during that time.
The midfielder was in a good place financially, mind, with his reported £110,000 a week in wages earning him a whopping £31 million – meaning Chelsea had to fork out more than £1 million per appearance. Drinkwater retired shortly after being released in 2022 and has undergone a dramatic career change, now working in construction.
Jadon Sancho, Borussia Dortmund to Manchester United (£73 million, July 2021)
Manchester United are responsible for some of the best transfers in Premier League history, but they have regularly missed the mark too, especially in the post-Sir Alex Ferguson era.
United had just finished a highly promising second under Ole Gunnar Solskjær and they splashed the cash to bring in Jadon Sancho from Borussia Dortmund, who at the time was one of the world’s most promising young players.
A graduate of arch-rivals Manchester City’s academy, Sancho had recorded some excellent numbers at Dortmund, registering 107 goal involvements in 137 appearances for the German side. United promptly stumped up £73 million for the 21-year-old, sticking him on a contract worth a breathtaking £250,000 a week, with high hopes that he could lead them to the title.
Instead, Sancho struggled to get going at Old Trafford, scoring just five goals and providing three assists in his maiden campaign. He soon fell out of favour after a similarly disappointing second season, but his vast wages meant that United found it impossible to offload him.
Instead, Sancho had loan spells at each of Dortmund, Chelsea and Aston Villa before being released on a free transfer. Chelsea even had an obligation to buy Sancho as part of their loan deal, but instead opted to pay a £5 million penalty to return him. The 26-year-old is yet to find a new club at the time of writing.
Antony, Ajax to Manchester United (£81.3 million, August 2022)
With Jadon Sancho struggling to make his mark, United went back into the market for a winger a year later, paying a monumental £81 million fee to sign Brazilian star Antony.
With the Red Devils parting company with Solskjær midway through the previous season, Erik ten Hag was tasked with leading the rebuild after guiding Dutch giants Ajax to back-to-back league titles and a Champions League semi-final.
Antony was a key part of that success and much was expected of the 22-year-old at Old Trafford, especially as he was the third most expensive signing in the club’s history at the time and the fourth highest in the league overall. Like Sancho, he was placed on a lucrative five-year contract, reported to be worth more than £100,000 a week.
The winger struggled in his first year in the Premier League, recording just six goal involvements from 25 appearances. The troubles didn’t stop there, with Antony then being blighted with domestic violence allegations at the start of his second season, leading to a leave of absence. He was regularly criticised for his poor attitude at United, with a string of disciplinary issues making him unpopular with fans.
Antony was loaned out to Spanish side Real Betis midway through the 24-25 season and enjoyed a surprisingly fruitful spell, eventually joining them permanently for £25 million.
Adrian Mutu, Parma to Chelsea (£15.8 million, August 2003)
Powered by the billions of new owner Roman Abramovich, Chelsea embarked on a massive spending spree in 2003, bringing in a whopping 13 players as they looked to take English football by storm.
Damien Duff, Juan Sebastian Veron, Hernan Crespo and Claude Makelele were the headline names, though Romanian forward Adrian Mutu was an eye-catching £15m purchase from Parma. The then 24-year-old had just finished second in the Serie A scoring charts with 18 goals and new manager Claudio Ranieri entrusted him with leading the line at Stamford Bridge.
It all started so well, too, with Mutu hitting the net four times in his first three games, including both goals in a pulsating 2-2 draw with London rivals Tottenham. The Romanian was promptly compared to the likes of Thierry Henry and Ruud van Nistelrooy, but his season quickly fizzled out, scoring just two more league goals in 22 appearances.
The striker’s second season at Chelsea was then dramatically cut short, with Mutu banned for seven months after testing positive for cocaine. The Blues promptly sacked the forward, before pursuing him in court for £15 million in damages. A lengthy legal battle would follow, but the courts eventually ruled in favour of Chelsea in 2009, before Mutu subsequently had appeals rejected by both the Court of Arbitration for Sport and the European Court of Human Rights.
Winston Bogarde, Barcelona to Chelsea (Free Transfer, August 2000)
It wouldn’t be a dodgy transfer rundown without tipping the hat to Winston Bogarde, whose stubborn antics inspired several who feature below in the notable mentions.
The experienced Dutch defender was snapped up on a free transfer from Barcelona and the lack of a fee enabled Bogarde to negotiate a lucrative four-year deal. He was viewed as a shrewd acquisition at the time, reportedly turning down advances from Arsenal, Leeds and Manchester United to head to Stamford Bridge.
Unfortunately for Bogarde, Gianluca Vialli was sacked just two weeks after bringing him in and his replacement Claudio Ranieri just didn’t fancy him, leaving the Dutchman in limbo. Chelsea tried on numerous occasions to move Bogarde on, but he was earning a reported £40,000 a week and as a consequence was more than happy to stay put.
With a transfer off the table as no club would cover his salary, Bogarde was forced to train with the reserves as his club put pressure on him to move on. He ultimately would be released having made just 12 appearances across four years, retiring soon after. Bogarde has since described his time at Chelsea as “terrible”, but his persistence earned him a cool £10 million.
Notable mentions
Marco Boogers, Sparta Rotterdam to West Ham (£850,000, July 1995)
Ali Dia, Unattached to Southampton (Free Transfer, November 1996)
Juan Sebastian Veron, Lazio to Manchester United (£28.1 million, June 2001)
Eric Djemba-Djemba, Nantes to Manchester United (£3.5 million, July 2003)
Andriy Shevchenko, AC Milan to Chelsea (£30 million, May 2006)
Bébé, Vitória to Manchester United (£7.4 million, August 2010)
Fernando Torres, Liverpool to Chelsea (£50 million, January 2011)
Roger Johnson, Birmingham to Wolves (£7 million, July 2011)
Jack Rodwell, Manchester City to Sunderland (£10 million, August 2014)
Ricky Alvarez, Inter Milan to Sunderland (£9 million, September 2014)
Mario Balotelli, AC Milan to Liverpool (£16 million, August 2014)
Saido Berahino, West Brom to Stoke (£12 million, January 2017)
Kepa Arrizabalaga, Athletic Bilbao to Chelsea (£71 million, August 2018)
Nicolas Pépé, Lille to Arsenal (£72 million, August 2019)
Jean-Kevin Augustin, RB Leipzig to Leeds (£18 million, January 2020)
Timo Werner, RB Leipzig to Chelsea (£45 million, June 2020)
Romelu Lukaku, Inter Milan to Chelsea (£97.5 million, August 2021)
Darwin Núñez, Benfica to Liverpool (£64 million, June 2022)
Kalvin Phillips, Leeds to Manchester City (£45 million, July 2022)
Mykhailo Mudryk, Shakhtar Donetsk to Chelsea (£88.5 million, January 2023)
By Nick Seddon
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