The 8 worst transfer windows from major clubs


Fans of Manchester United, Liverpool, Arsenal and Chelsea will know how this feels when a Premier League heavyweight suffers a shocking transfer window.

Newcastle United are currently enduring a nightmare summer transfer window. Star man Alexander Isak has made clear his intentions to leave and Eddie Howe is struggling to land his favoured targets.

We’ve taken a closer look at eight of the worst-ever transfer windows from big Premier League clubs.

Manchester United (2009)

Sixteen years on, there remains an argument that Cristiano Ronaldo in his first stint at Manchester United is as good as any Premier League footballer has ever been.

He fired Sir Alex Ferguson’s Red Devils to three successive league titles, was the last Premier League player to lift the Ballon d’Or before Rodri and moved to Real Madrid for a world-record fee.

Then he became their all-time top goalscorer, averaging over a goal a game over nine years, and won a further four Ballon d’Or and four Champions League medals.

Mame Biram Diouf, Michael Owen and Gabriel Obertan(!) were never going to fill a void like that, were they?

Only the arrival of Antonio Valencia, a future fan favourite, stopped that window being a total unmitigated disaster.

Liverpool (2010)

“I thought I would stay one more year and take it as a transition season. But a time comes when you lose enthusiasm, you see those in the Spanish national team are playing at a different level,” Fernando Torres recalled of his £50million move to Chelsea in January 2011.

“Then when everything looked black, Chelsea came and showed a real interest.”

Imagine going from the pinnacle of your career, lifting the World Cup, to returning to your club, who sold Javier Mascherano (following Xabi Alonso’s departure the year before) and signed Joe Cole, Milan Jovanovic, Christian Poulsen and Paul Konchesky.

All the while replacing Rafael Benitez with Roy Hodgson.

No wonder everything looked bleak to Torres, who evidently could only stomach six months after their major downturn. The nadir of the disastrous Hicks & Gillett era.

Manchester City (2012)

Challenging their city rivals’ 2009 for the worst summer window from a reigning Premier League champion, City never had the excuse of losing their star player.

The state-backed project didn’t rest on their laurels after Sergio Aguero’s last-gasp heroics. They backed Roberto Mancini with over £50million of reinforcements – back when that was still a sizeable sum of money.

But the infamous quintet of Javi Garcia, Matija Nastasic, Jack Rodwell, Scott Sinclair and Maicon struggled to raise City’s level, and they ultimately endured a miserable failure to retain their first title.

Robin van Persie and Eden Hazard reportedly chose Manchester United and Chelsea over offers from City that summer. How different things might’ve been, eh?

Tottenham (2013)

Here’s your obligatory reference to “selling Elvis and signing The Beatles” – one of the great football quotes, if only for how badly it aged. Thank you, Garth Crooks, for your services to comedy.

Christian Eriksen was a sensational signing. But Paulinho, Roberto Soldado, Etienne Capoue, Vlad Chiriches and Nacer Chadli were very much not.

Erik Lamela belongs somewhere in the middle of that scale, if only for his services to sh*thousery and scoring rabonas.

QUIZ: Can you name the Premier League’s 25 most expensive foreign sales ever?

Liverpool (2014)

There’s a theme emerging here. Manchester United after Cristiano Ronaldo. Tottenham after Bale. Look further afield to Barcelona after Neymar.

Newcastle might be set to receive a colossal British transfer record fee for Isak… but reinvesting that money on an adequate replacement will be much easier said than done.

Just ask Liverpool, who bought Rickie Lambert, Lazar Markovic and Mario Balotelli after selling Luis Suarez to Barcelona. Ooooof.

Adam Lallana, Dejan Lovren and Emre Can were useful enough, at least. And Divock Origi became a proper Kop cult hero. So not as bad as 2010 – but still pretty rotten.

Arsenal (2015)

In hindsight, this was a vital hinge point in the latter days of Arsene Wenger’s reign and Arsenal’s slow, painful descent into utter mediocrity.

Following the move to the Emirates, Arsenal were well-versed in losing their key players.

But after the likes of Ashley Cole, Thierry Henry and Cesc Fabregas jumped ship – plus the many that went to post-takeover Manchester City – the summer of 2015 was one in which Wenger kept the core of his team together.

With Alexis Sanchez and Mesut Ozil at the peak of their powers, the Gunners looked in a position to compete.

And they did for two-thirds of the 2015-16 campaign, in which all of the traditional big guns suffered major missteps and Leicester City pulled off a fairytale.

Looking back, they might well have crushed the Foxes’ dreams were it not for their sheer inertia and lack of ambition in the summer of 2015.

Petr Cech came in with title-winning experience, but on the downslope… and that was about it. Another quality addition or two and you can’t escape the feeling it would’ve been their year.

Chelsea (2017)

You imagine that Jose Mourinho had a little chuckle to himself while watching Antonio Conte suffer something akin to what the Italian called “a Mourinho season” in 2017-18.

Conte had specified that the Blues must avoid a repeat of Chelsea’s disastrous title defence in 2015-16… which was perhaps an omen for the choppy waters ahead.

Chelsea never quite plumbed those mid-table depths, but their title defence was similarly non-existent.

Unlike their struggles under Mourinho, which appeared sparked by a behind-the-scenes meltdown, Conte’s downfall can be traced back to disastrous summer spending.

Replacing snarling bad boy Diego Costa with angelic choir boy Alvaro Morata looked like a poor decision from day one. Not to mention that he signed for a club-record fee.

Add to that Danny Drinkwater and Tiemoue Bakayoko signing for a combined £75million and you have yourself a recipe for catastrophe.

Chelsea (2022)

Somehow, Chelsea outdid their 2017 transfer dealings five years later – as Todd Boehly announced himself as the new sheriff in town with a downright bizarre trolley dash that looks worse with every passing year.

Wesley Fofana, Marc Cucurella, Raheem Sterling, Kalidou Koulibaly, Carney Chukwuemeka, Pierre-Emerick Aubameyang, Gabriel Slonina and Denis Zakaria were signed to the tune of almost £300million(!).

Cucurella has taken time to get up to speed but has played his part in the club’s post-Abramovich rise.

Fofana could yet prove a decent buy if he can put his injury woes behind him. The less said about the others, the better.

Chelsea’s Club World Cup trophy is a marker they’re back on the right track. But the ghosts of 2022 still linger – it’s been a serious fumigation job over the past three years.


READ NEXT: The 10 players with the highest combined transfer fees: Joao Felix enters top five…

TRY A QUIZ: Can you name the 30 most expensive transfers between Premier League clubs?



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