Man Utd, Liverpool, Arsenal: The Premier League 'big six' clubs' worst ever transfer windows

  • Kobe Tong

The January transfer window can often be a time for carnage in the Premier League.

With clubs fumbling around for mid-season buys, you can find panicked purchases such as Fernando Torres to Chelsea, Andy Carroll to Liverpool and Aleix Sanchez to Manchester United.

Sadly, those in the know aren’t predicting such madness from the 2021 edition given the financial strain on clubs right now, but sometimes the weirdest signings come when you least expect them.

Premier League panic buys

We’ll certainly be keeping our fingers crossed for that but in the meantime, we wanted to look at a few instances in transfer windows generally where clubs got things terribly wrong across the board.

That’s right, forget individually poor signings, we’re talking about terrible windows as a whole and we’re gunning for the high-profile examples by honing in on the Premier League’s ‘big six’.

The so-called conglomeration of the Premier League‘s biggest hitters have all been guilty of misplacing their millions over the years as the Daily Mail highlighted this week.


Worst ‘big six’ transfer windows

And inspired by their picks for some truly horrendous transfer windows, we’ve selected the most damning examples that come to mind for all six clubs over the last ten years:

Arsenal – Summer 2016

Bought: Shkodran Mustafi (£35 million), Granit Xhaka (£30 million), Lucas Pérez (£17 million), Rob Holding (£2 million) and Takuma Asano (£800,000)

Sold: Serge Gnabry (£5 million), Tomas Rosicky (free), Isaac Hayden (£2.5 million) and Mathieu Flamini (free)

Holding has proven to be a shrewd signing, granted, but Mustafi has been as mistake-prone as they come, Xhaka has brought with him controversy in spades and Perez lasted just one season leading the line.

Combine that with the signing of the little-known Asano who never played because he was refused a work permit and flogging a future Champions League winner for a truly dire summer for the Gunners.


Chelsea – Summer 2017

Bought: Willy Caballero (free), Antonio Rüdiger (£29 million), Tiémoué Bakayoko (£40 million), Alvaro Morata (£58 million), Davide Zappacosta (£23 million) and Danny Drinkwater (£35 million)

Sold: Asmir Begović (£10 million), Dominic Solanke (tribunal), Loïc Rémy (free), John Terry (free), Juan Cuadrado (£17.3 million), Christian Atsu (£6.2 million), Bertrand Traoré (£8.8 million), Nathan Ake (£20 million), Nathaniel Chalobah (£5 million) and Nemanja Matic (£40 million)

The Blues have a knack for terrible transfer windows the summer after they win the Premier League because the summer of 2015 could easily have been chosen too, but three of these signings take the cake.

Morata couldn’t come close to filling Diego Costa’s boots, Bakayoko is one of the biggest Premier League flops in recent memory and Drinkwater was last seen being sent off for the club’s youth team.


Liverpool – Summer 2010

Bought: Jonjo Shelvey (£1.7 million), Milan Jovanovic (free), Danny Wilson (£2 million), Joe Cole (free), Christian Poulsen (£4.5 million), Brad Jones (£2.3 million), Raul Meireles (£11.5 million) and Paul Konchesky (£3 million)

Sold: Yossi Benayoun (£5.5 million), Albert Riera (£4 million) and Javier Mascherano (£17.25 million)

Ah, transfer windows don’t come much more infamous than this with Roy Hodgson digging his own grave at Anfield with a slew of terrible signings as Poulsen and Jovanovic lasted just one season in England.

Meanwhile, Wilson only ever made two Premier League outings, Konchesky looked completely out of his depth and losing Mascherano to Barcelona was a huge blow ahead of Fernandes Torres’ January exit.


Manchester City – Summer 2012

Bought: Jack Rodwell (£12 million), Richard Wright (free), Scott Sinclair (£6.2 million), Maicon (£5 million), Matija Nastasić (£12 million) and Javi Gracia (£17 million)

Sold: Emmanuel Adebayor (£5 million), Adam Johnson (£12 million), Nigel de Jong (£3.1 million) and Stefan Savic (swap)

There were no departures that Roberto Mancini would have been losing sleep over, but City clearly paved the way for Chelsea when it comes to defending Premier League titles with woeful signings.

Rodwell and Sinclair are two of the worst transfer clangers we’ve seen from a ‘big six’ club, Wright never actually played, Maicon was past his sell-by date and Nastasić and Gracia never looked convincing.


Manchester United – Summer 2014

Bought: Ander Herrera (undisclosed), Luke Shaw (undisclosed), Marcos Rojo (£16 million), Angel Di Maria (£59.7 million), Daley Blind (£14 million), Timothy Fosu-Mensah (undisclosed), Victor Valdes (free) and Radamel Falcao (loan)

Sold: Alexander Büttner (£4.4 million), Federico Macheda (free), Nemanja Vidic (free), Patrice Evra (£1.2 million), Bebe (£2.4 million), Shinji Kagawa (undisclosed), Danny Welbeck (£16 million), Rio Ferdinand (released), Anderson (free), Wilfried Zaha (£3 million), Darren Fletcher (free) and Michael Keane (undisclosed)

What makes this transfer window so painful is that it actually looks decent on paper and to be fair, the trio of Herrera, Shaw and Blind turned out fine, but this was a summer of expensive mistakes for United.

Falcao and Di Maria are always touted as two of the worst signings in Premier League history, while it also marked a summer where United lost a slew of club legends such as Vidic, Ferdinand and Evra.


Tottenham – Summer 2013

Bought: Paulinho (£17 million), Nacer Chadli (£7 million), Roberto Soldado (£26 million), Etienne Capoue (£9 million), Vlad ChiricheÈ™ (£8.5 million), Christian Eriksen (£11.5 million) and Erik Lamela (£30 million)

Sold: Steven Caulker (£9 million), Clint Dempsey (£6 million), Tom Huddlestone (£5 million), Scott Parker (£3.5 million), Massimo Luongo (£400,000) and Gareth Bale (£85.3 million)

No summer can be a good summer when you flog your star player regardless of whether it’s for a world-record transfer fee, but it’s an even worse summer when you blow the money on a series of flops.

Yes, Eriksen turned out to be an inspired purchase, but Soldado struggled for goals in England, Lamela has never really lived up to the hype and Paulinho was voted as Tottenham’s worst ever signing. Yikes.


So, it goes to show that even big bucks don’t guarantee you success with the likes of Falcao coming through the entrance and Bale striding out the exit. Money can’t buy you everything, huh?

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