Ranking 13 of the weirdest Prem deadline day transfers this decade

Quick Reads

As the transfer deadline draws closer, Premier League clubs will be getting that bit more desperate in their pursuit of new recruits.

Some will be willing to take a punt on someone who might be able to do the trick immediately, while others will prefer to look longer-term, but there will always be the occasional strange pick-up at the end of August.

We’ve gone back through every deadline day this decade and picked out some of the weirder deals involving Premier League clubs… as well as a few from elsewhere. They’re ranked, as always, in order of weirdness.

13. Michael Essien – Real Madrid

Michael Essien was clearly on his last legs at Chelsea in 2012, having played just nine games under André Villas-Boas and 10 under Roberto di Matteo, staying on the bench for the Champions League final.

We expected him to take a step down, and a move to Panathinaikos – who he joined in 2015 – would have seemed about right. Real Madrid, though? They had good players – why did they need someone who’d played fewer games than a 20-year-old Oriol Romeu?

He even played in more than half of Los Blancos’ league games, before returning to Stamford Bridge and actually featuring in the 2013-14 season.

READ: Michael Essien, Chelsea’s selfless hero, and the folly of utility men

12. Royston Drenthe – Everton

One year earlier, Real Madrid had let one of their own players move to the Premier League.

Royston Drenthe had been out on loan the previous season at Hércules, so the prospect of the Spanish giants letting him go wasn’t out of the ordinary, but it seems fair to say the erratic Dutchman has never struck us as a typical David Moyes player.

He scored a couple of goals, but – in a move none of us could have seen coming – he upset Moyes with his off-field antics and was frozen out. If only there had been a single clue.

11. Joe Hart – Torino

Hart knew he’d need to find a new club after Pep Guardiola arrived at Manchester City in 2016, but Torino weren’t at the top of most people’s lists.

They’d just finished 12th in Serie A and replaced manager Giampiero Ventura with Siniša Mihajlović, while they already had a settled goalkeeper in Daniele Padelli – there were plenty of reasons for him not to move there.

Hart had a reasonable season, though – certainly better than his 2017-18 campaign at West Ham.

10. Kevin Doyle – Crystal Palace

Crystal Palace struggled for goals in the 2013-14 season, finding the net just 33 times – only relegated Cardiff and Norwich managed fewer.

The solution? Signing someone who spent half of the previous season in League One and the other half in the Championship, scoring just five times in the process.

Doyle’s only goal came against non-league Dover Athletic, which is about as much as you’d expect.

9. Regan Poole – Man Utd

Poole will surely go down in history as the only youngster who Louis van Gaal didn’t play during his time at Old Trafford.

More confusingly, he stuck around until 2019 without making it onto the pitch for the first team. A football league player in a Premier League club’s clothing.

READ: Where are they now? The 15 kids handed Man Utd debuts by Van Gaal

8. Joe Cole – Lille

We still haven’t really got our heads around Cole commuting from London to Lille via the Eurostar, while the fact that he played in the same team as Eden Hazard and Dimitri Payet makes us drool.

He was pretty good there, too, scoring nine times in all competitions and seeming to reinvigorate his England hopes. Ultimately, though, it was a false dawn and he wouldn’t add to that final international cap from 2010.

7. Ricky Álvarez – Sunderland

Álvarez’s initial move to Sunderland in 2014 wasn’t too weird, even if Gus Poyet’s exit saw his first-team chances limited.

More bizarrely, though, a registration dispute (Inter thought Sunderland were required to make the move permanent; the Black Cats disagreed) meant that, for a time, he was referred to as ‘a professional footballer for Inter or Sunderland’. That feels like enough of an oddity to earn him a spot here.

6. Micah Richards – Fiorentina

When Micah Richards retired in 2019, he did so amid comments about unfulfilled potential. Back in 2014, though, he was long overdue a move away from Manchester City after playing fewer than a dozen league games in two years.

Italy didn’t seem like the obvious choice, though, and his one year loan at Fiorentina wasn’t turned into a permanent deal. He did get to play with Mo Salah, at least.

5. Richard Wright – Man City

When Richard Wright left Preston in July 2012, just a week after signing, he said: “I’ve only been away from home for a few days and I know already that I cannot live that far away from my family.”

Later that summer, he signed for Manchester City.

The distance between Ipswich (his home) and Preston is 199 miles. The distance between Ipswich and Manchester is 185 miles. That must have made all the difference.

4. Nicklas Bendtner – Juventus

We’ll never tire of that photo of Bendtner and Nicolas Anelka celebrating Juve’s 2013 title win, having contributed next to nothing to that season.

Or, indeed, any of their other games.

3. Joey Barton – Marseille

It’s rare for a transfer to sneak up on you and hit you when you weren’t looking, but if… look you know where we’re going with this one.

2. Papy Djilobodji – Chelsea

Signing a player and immediately leaving them out of your European squad feels like at best a breakdown in communication and at worst a dumb move from everyone involved.

Obviously Sunderland letting Chelsea double their money a year later was even dumber, mind.

1. Saphir Taïder – Sassuolo

You’re probably wondering why we have a deal between two Italian clubs at the top of this list when all the others include English clubs. Well, as it turns out, this one does too.

Taïder signed for Southampton on loan from Inter on a season-long loan deal in August 2014, playing for the Saints in pre-season. So far, so normal.

However, before the month was up, and before the Algerian had played a single league minute, the deal was cancelled and he was farmed off to Sassuolo amid rumours that he didn’t fit manager Ronald Koeman’s work ethic.

His work ethic didn’t stop him playing more than 25 times for his new club, though, or more than 50 for Bologna.

We’re still baffled by this one.


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