The winter window is an attractive time to do business, potentially giving clubs an edge in the race for trophies, survival or a push for the European crown.
The January 2025 transfer window is now open and business is light compared to previous years. Arsenal are in the market for a striker, with Manchester City likely to spend big money and Ruben Amorim looking to make his first senior signing as Manchester United manager.
There’s a reason Premier League managers try to avoid doing too much business at the end of the year and the beginning of the year, though. January tends to make more mistakes, four four two Take a look at some of the biggest mistakes in date order.
1. Mihajlo Mudrik (Shakhtar Donetsk to Chelsea, 2023 £89 million)
People were surprised when Chelsea spent more than £85 million on a winger who had only scored nine goals in his career. The high price tag did little to ease the pressure on Mudrik’s shoulders, as the Ukrainian came under intense scrutiny from his first touch of the ball.
However, he had a terrible time at Chelsea, scoring just five goals in 53 games and failing to live up to his high price tag. Chelsea are thriving under Enzo Maresca but Mudric still has not become a key part of the new manager’s plans, with the £89m player instead being retained for the Europa League.
2. Henrikh Mkhitaryan and Alexis Sanchez (Swap Deal, 2018)
Henrikh Mkhitaryan was widely regarded as one of the worst swap deals of the 21st century, moving from Manchester United to Arsenal, while Alexis Sanchez moved the other way . Sanchez ranks 15th on FourFourTwo’s list of the best wingers in Premier League history, and his performance at Arsenal has been nothing short of brilliant. Despite winning two FA Cups with Arsenal, he wanted to improve his chances of winning trophies and pushed for a move to Manchester United.
The Chilean failed to win the trophy as he scored just three goals in 32 games. Mkhitaryan fared slightly better, lasting just over half a season and scoring eight goals. But the hype surrounding the swap was far greater than the player’s performance.
3. Cenk Tosun (Besiktas to Everton, 2018, £27 million)
Tosun has scored over 40 goals in two seasons for Besiktas and looks to be a shrewd signing for Everton. However, the Türkiye international failed to adapt to England. The constant change of managers at Goodison Park, with Dominic Calvert-Lewin’s improved form not helping matters.
Four years later, he returned to Besiktas on loan from Crystal Palace and made 55 appearances in England, scoring just 10 goals at a cost to Everton of nearly £3 million per goal.
4. Guido Carrillo (Monaco to Southampton, £19.1 million, 2018)
Having £75m in your pocket can do strange things to football clubs. Southampton, who are facing relegation threats after selling Virgil van Dijk to Liverpool, want to sign a statement to show fans they remain ambitious and secure a move under Mauricio Pellegrino at the end of January. He averaged just one goal per game, giving him more firepower.
As it turns out, Carrillo wasn’t the answer. The Argentinian striker was a big-money acquisition and helped Monaco win the Ligue 1 title in 2016/17, but he ended up starting just seven games (five in the league) and never scored for Saints. ball as the Saints barely avoided relegation. Incoming head coach Mark Hughes has only played him twice since mid-March and he was loaned to Leganes in 2018 before leaving permanently in 2020.
5. Juan Cuadrado (Fiorentina to Chelsea, 2015 £23.3 million)
As league leaders, Chelsea didn’t have to do much in January 2015; indeed, it was mainly Jose Mourinho who confirmed the signings of Andre Schürrle, Mark Schwarzer, Fernando Torres and With the exit of fringe players such as Ryan Bertrand, the latter two formalized their existing loan deals. The only signature was signed on February 2, 2015: fleet-footed Fiorentina winger Juan Cuadrado.
The Colombian made just four starts and Mourinho, ranked 12th on FourFourTwo’s list of the greatest managers of all time, said “he will be great next season” – and indeed, he certainly impressed. impression, but after a loan spell at Juventus, Juventus signed him and hired him permanently in the summer of 2017. What’s even more exciting? As part of the £22.3m deal that brought Cuadrado to Chelsea, the Blues loaned Fiorentina a winger named Mohamed Salah…
6. Kostas Mitroglu (Olympiacos to Fulham, 2014, £12.4 million)
Fulham signed Mitroglou in early 2014 for a club-record transfer fee. Granted, Cottagers have also added Johnny Heitinga and Lewis Holtby on deadline day, but Olympiacos’ prolific marksman is tipped to be the man who can score goals for Rene Meulensteen Players who remain in the Premier League.
But he can’t. Mitroglou fell out of favor with Meulensteen’s successor Felix Magath and started just one game in the EFL as Cottagers fell into the Championship.
7. Kim Kallstrom (loaned to Arsenal from Spartak Moscow, 2014)
It was a strange acquisition indeed, even if Arsenal didn’t pay a transfer fee. The Gunners were in desperate need of a striker midway through the 2013/14 season (and as always, you can’t go wrong with a centre-back and defensive midfielder) – but Wenger instead opted to bring in an aging, injury-prone player. Attacking midfielder on a four-month loan.
Unsurprisingly, Karlström’s debut was delayed due to fitness issues and Arsenal went ahead with the deal despite a back problem being revealed during the Swede’s medical. He finally made his debut against Swansea in late March, one of just four appearances for the north Londoner before returning to Spartak Moscow at the end of the season.
8. Fernando Torres (from Chelsea to Liverpool, £50m in 2011) and Andy Carroll (from Newcastle to Liverpool, £35m in 2011)
When Torres moved from Anfield to Stamford Bridge in January 2011, there were already signs that his form was on the decline, but Chelsea learned from the experience. The huge transfer fee of 50 million pounds only bought 20 Premier League goals in three and a half seasons, which gave Liverpool fans a chance to gloat.
Or at least that would be the case if the Reds didn’t spend the bulk of their earnings on Andy Carroll, Liverpool’s tenth most expensive signing ever. He scored 11 goals in 58 games and spent a miserable 18 months on Merseyside, completely unsuited to the Reds’ style of play.
9. Savio Nsereko (Brescia to West Ham United, 2009 £9 million)
As of January 2025, Savio’s last clubs include Atyrau (Kazakhstan), Letava Jonava (Lithuania), Belo Stara Zagora (Bulgaria), Pippins Reed (Germany) and BSC Sendling (Germany), which may be more telling than Savio’s true ability level. In early 2009, he moved to West Ham United for £9 million.
The Hammers presented the former Germany U20 international with the number 10 jersey at Upton Park, but he failed to live up to expectations and only started in the Premier League (he came on as a substitute in nine other games) before being sent away Seven months after going to Florence.
10. Alfonso Alves (Heerenveen to Middlesbrough, £12.5m, 2008)
Signing a striker from the Dutch top flight is a hit-or-miss affair. For every Ruud van Nistelrooy there’s a Vincent Janssen, for every Luis Suarez there’s a Mattha Kezman, for every Robin van Persie there’s a Siamese Jong.
Afonso Alves is another member of the ‘Mademoiselle’ crowd who made a truly bizarre appearance at Middlesbrough. He scored 45 goals in 39 Eredivisie games for Heerenveen, while in 18 months at Middlesbrough he scored just 10 goals in 42 games and was eventually relegated.
11. Jean-Alain Boumsong (Rangers to Newcastle United, 2005 £8 million)
It was a strange acquisition on many levels, with Graeme Souness’ Newcastle United paying Rangers £8m for Boumsong’s services just months after he came on for free. In fact, the 2007 Stevens inquiry scrutinized the transfer and found no irregularities.
The 27-cap France international actually began his career at St James’ Park, but basic defensive errors soon began to seep into his game. Juventus, who had been relegated to Serie B just a few months earlier, took Boumsong away from the Magpies in August 2006, although he never made another Serie A appearance following his return to the Old Lady.
