
10 of the craziest January transfers in the Premier League
With another crazy transfer window done and dusted, here’s a look at the biggest January signing failures in the Premier League’s history. Stream all Premier League games live on Showmax Pro, courtesy of SuperSport.
Alexis Sanchez – Arsenal to Manchester United
This is one of the prime examples of why one should be hesitant to buy players in the hyper-inflated January transfer window.
Alexis Sanchez came in as hot property at Arsenal and was offered the highest wages in Britain to join Manchester United in order to challenge Manchester City.
Eighteen months, 32 matches and only three goals later, United arguably went to more trouble loaning out Sanchez than buying him in the first place.
Philippe Coutinho – Liverpool to Barcelona
Coutinho’s transfer to Barcelona is extraordinary for two reasons.
Firstly, the price that Barcelona paid was so inflated (£105 million with options to rise to £142 million) that it ended up funding the whole core of a Premier League-winning team for Liverpool.
Secondly, it provided one of the most extraordinary situations of a player on loan punishing the parenting club. Coutinho was loaned out to Bayern Munich where he not only played against Barcelona in a humiliating 8-2 thrashing, but he also scored twice.
Fernando Torres – Liverpool to Chelsea
Torres will always be remembered as a goalscoring machine at Liverpool. However, at Chelsea, he will always be a poster boy for their "cursed" number nine shirt.
It appeared to be a vanity signing by Roman Abramovich at the time when he broke the British transfer record by paying a fee of £50 million.
He was supposed to be a guarantee for 20 goals per league season. Instead, he took as many as four seasons to reach that mark.
Jean Makoun – Lyon to Aston Villa
Gerard Houillier signed the midfielder with much fanfare as a promising player with UEFA Champions League experience.
The return on his £6.2 million price tag ended up being nine games in two years with his most memorable contribution being a red card for an awful tackle in a game against Blackpool.
Upon his departure, the new Aston Villa manager Paul Lambert said he “had not got a clue what he looks like”.
Juan Cuadrado – Fiorentina to Chelsea
Oh dear. Chelsea are featuring quite a lot on this list.
Cuadrado is an example of a player becoming overrated on the back of having one good FIFA World Cup tournament. Everyone was fighting for his signature after his performances for Colombia in 2014. Chelsea bid highest and have regretted it since.
Ended up being £26 million pounds for a player that only started four times. Ouch.
Jean-Alain Boumsong – Rangers to Newcastle
Unlike the exciting times Newcastle are experiencing now, they used to be a squad rife with failed transfers and Boumsong was the most disastrous of them all.
Eyebrows were raised when the club paid £8 million pounds for a defender that Rangers had signed on a free transfer six months earlier. After two seasons that produced an endless stream of defensive errors, the Frenchman was jettisoned off to Serie B.
Chris Samba – Anzhi to QPR
He was signed as a solid centre-back to help in a relegation fight on wages reportedly around £100 000 a week.
His spell was disastrous, with the low point being a Twitter spat with fans, telling them they had to “get over” how much he was being paid.
Guido Carillo – Monaco to Southampton
It flies under the radar in the history of failed transfers, but how in the world did Southampton part with £19 million for Guido Carillo?
An untried striker at Monaco who was an understudy to Kylian Mbappe and Falcao, the French outfit must have laughed all the way to the bank when that bid came in.
Carillo played seven games without scoring. So it nearly ended up costing the Saints £3 million per appearance.
Enzo Fernandez – Benfica to Chelsea
Many of you will be up in arms that an as-yet untested player made this list, but on the outset this is the most extraordinary case of over-inflation winning over common sense.
Before the FIFA World Cup, the Argentinian was available for £16 million. After the World Cup, Chelsea ended up having to pay £106 million for his services.
New owner, same Chelsea.
Mykhailo Mudryk – Shakhtar Donetsk to Chelsea
Yes, another untested player that you will say is unfair to be on this list. But hear us out.
In the Ukraine, he only played 50 games with a scoring ratio that’s worse than one in every five games. Is this really what £89 million pounds buys you these days?
Chelsea have without doubt taken the prize this January for the craziest transfer activity, with this signing of Mudryk being the most eyebrow-raising of the bunch.
Why Showmax Pro?
Showmax Pro is a streaming service available for Showmax subscribers in Africa that bundles the Showmax entertainment offering with music channels, news and live sports streaming from SuperSport.
Subscribers can live stream the latest seasons of the English Premier League, LaLiga, Serie A, TotalEnergies African Nations Championship, UEFA Europa and UEFA Conference leagues.
The platform also offers a wide range of other live sports events including athletics, professional boxing, and the world’s biggest marathons. Visit showmax.com to learn more or to subscribe to Showmax Pro.
Join the conversation on social media by following and interacting on the below pages:
Twitter: @ShowmaxPro
Instagram: @ShowmaxPro
Facebook: @ShowmaxPro
More like this

Vilakazi's verdict: Sundowns to "edge it" in high-stakes MTN8 semi-final
This weekend, all eyes will be on Lucas Moripe stadium as Mamelodi Sundowns face off against Orlando Pirates in the MTN8 semi-final.

Rivalries reignite in thrilling Premier League games on Showmax
The Premier League drama is back in full swing, and this coming weekend promises another thrilling rollercoaster ride for football fans worldwide.

The Big 6ix on new Premier League season and their SA adventure
Showmax Premier League caught up with The Big 6ix to hear their new season predictions and verdict on their South African trip.

Will anyone stop the champs? Booth on Downs' quest for a 9th title
The Betway Premiership officially kicks off this weekend, and Showmax Premier League has you covered with all the action. Catch Mamelodi Sundowns take on Chippa United on Saturday, 9 August 2025, at 15:00.

The curtain rises: Wembley Showdown - LFC vs Crystal Palace
This Sunday, Wembley Stadium will host the FA Community Shield, an epic clash between Premier League champions Liverpool and FA Cup winners Crystal Palace. Catch the action live on Showmax PL.

Showmax Premier League weekly watchlist: 19-25 August 2025
Stream all Premier League and PSL games live on Showmax Premier League.

Showmax PL kicks off football fiesta with MTN8 quarter-finals
Stream the MTN8 quarter-finals on Saturday, 2 August, and Sunday, 3 August, live on Showmax Premier League.

Melissa Kape Saili tips Morocco to win WAFCON final
Ahead of the WAFCON final, former Zambia star player Melissa Kape Saili shares her prediction on whether Morocco or Nigeria will take the title. Stream it live on Showmax Premier League on Saturday, 26 July.
SA celebs open up about divorce on Untied
Youngins S3, coming soon to Showmax
Latest Stories

Vilakazi's verdict: Sundowns to "edge it" in high-stakes MTN8 semi-final

Rivalries reignite in thrilling Premier League games on Showmax

5 patients you’ll meet in The Pitt Season 1

Palesa Mphaki on being Married at First Sight, her husband and more

5 new reality shows on Showmax in August

The Big 6ix on new Premier League season and their SA adventure

Will anyone stop the champs? Booth on Downs' quest for a 9th title

The curtain rises: Wembley Showdown - LFC vs Crystal Palace

Showmax Premier League weekly watchlist: 19-25 August 2025

Showmax PL kicks off football fiesta with MTN8 quarter-finals

Melissa Kape Saili tips Morocco to win WAFCON final

Must-watch trailer: upcoming Showmax reality show Vaal Riviera

Showmax PL kicks off new football season with unmatched action

Shaka iLembe's Dawn Thandeka King on Untied

Giants: Buccaneers' untold story streams live on Showmax PL

Ugochi Oparanozie backs Nigeria to overcome Banyana Banyana

Director Jasyn Howes on true-crime documentary The ABC Killer

Get Ready for the PL Summer Series – live on Showmax

Nthabeleng Modiko backs reigning champions for WAFCON glory

Felix Hlophe on his comedy special, fat jokes, sex and cheating

Everyone Else Burns and 8 more cult classics

Binge five of the 10 biggest Emmy nominees on Showmax

Dangerous minds in The Institute + 7 more superpowered series

Londie London on RHOD: "There's genuine history and love there"