Sex toys, mad money and airport heists – the wildest moments in transfer deadline-day history

Like school proms and posting pictures on social media of your breakfast, transfer deadline day is a tradition that has not been long in our lives. As recently as the 1990s, players could move from club to club throughout the season. No window slammed shut on dealings then. No countdown clock chimed. No yellow ties were worn.

In 2002, however, the Premier League, recognising that such a free-for-all could be exploited by those clubs seeking reinforcements for a title charge, or to head off relegation, decided that trading should be restricted to just two periods: between June and the end of August ahead of things kicking off, and then throughout January to allow for fresh recruitment before the business end of the season.

Sensing that there was potential for eyeball-grabbing drama in any last-minute shenanigans, the Premier League’s principal broadcaster Sky quickly turned the last day into a rambunctious, rolling news event. Reporters were dispatched around the country to deliver updates from outside training grounds, where they were surrounded by fans. On the final day of the season as many as 270 live, on-the-spot reports would be offered up in 24 hours of continuous broadcast. Each one gave opportunity both to supply and – as the British public quickly caught on to the idea that this was the swiftest way to get themselves on live telly – to make news.

Here are some of the best/weirdest moments in descending order.

10: The airport heist

August 2008

Manchester United assumed they had just strengthened their Champions League-winning side by signing Dimitar Berbatov from Tottenham. Straightforward enough. Except Manchester City had just been taken over by Sheikh Mansour. And to demonstrate that with his bottomless pockets had come proper ambition, City’s management decided to try to intercept the Berbatov deal by the simple process of flinging large amounts of money at him. So concerned was United manager Sir Alex Ferguson by the attempted coup, he drove to Manchester airport to meet the player as he stepped off the plane from London, ready to intercept any representatives from his neighbours. He succeeded in a way you suspect would not be quite so easy 16 years on.

9: Banana attack

January 2016

A clip of a correspondent for Italian broadcaster SportItalia standing outside Stamford Bridge earnestly reporting on Alexandre Pato’s move to Chelsea went viral. Not because of his straight-faced delivery, not because Pato was going to tear up trees in England, but because as he spoke he was approached by a man in an Arsenal shirt carrying an inflatable banana. The photo-bomber proceeded to interrupt the broadcast by assaulting the correspondent with his prop. After trying to push him away, the reporter lost his temper, seized the banana and beat his trolling assailant round the head with it, before returning to his post and politely signing off his report.

If it looked like something from a sitcom that was largely because it was. The reporter was the Italian comic actor Paolo Gasparini. And the idea was to see how quickly his report – mimicking the interactive possibilities of deadline-day broadcasts – could go viral. The answer was: very quickly. It was shared nearly a million times, including by several prominent Italian players.

8: Professional standards

January 2011

After selling their talismanic striker Fernando Torres to Chelsea for £50 million, Liverpool quickly plugged the gap by doing perhaps the best bit of business in deadline-day history: they signed Luis Suárez from Ajax for just £22.2 million. But the bargain of the century was somewhat diminished by the fact that on the same day, they also paid £35 million to bring Andy Carroll down from Newcastle. As manager Kenny Dalglish introduced his two new players to the cameras, the look of utter disdain on Suárez’s face was a picture. It did not take a specialist in facial recognition to interpret his expression. “What?” it seemed to say. “You mean you paid £13 million quid more for him than you did for me?”

7: Blame the fax machine!

August 2015

The fax machine has often been a significant player in deadline-day drama. Never more so than when Real Madrid thought they had bought David de Gea from Manchester United for £29.3 million plus Keylor Navas. Everything had been agreed. But then, at the very moment the window shut, the paperwork got somehow trapped in the fax system.

Given that by then faxes were largely obsolete and any signatures could have been applied digitally, it seemed incomprehensible that such a breakdown could happen. Each side blamed the other for the stand-off and De Gea was obliged to stay in Manchester for a further eight years. Though it was not that much of a hardship. He managed to parlay the fax up into an improved contract which made him one of the best-paid players in the club’s history.

6: User-generated content

January 2022

Despite the resources Sky throws at deadline day, the broadcaster does not always get the big scoops. When Jermain Defoe returned to Sunderland, the news was announced by a supporter called Wee Phillie, reporting live on Facebook for SAFC Fan TV. He had somehow infiltrated the Sunderland training camp and had wandered up to the reception area where, through the window, he could see an interview was being conducted with a new signing. As he stood outside, he told his many viewers, with some disappointment, that it was not Defoe – as had been rumoured but “that lad from Fleetwood”.

As he was leaving the premises despondently, however, a car passed him. He mimed at the passenger to wind down the window and then leapt in the air in delight when he recognised who it was. “It’s only Jermain Defoe!”

In the history of broadcasting, few exclusives can ever have been so cheerfully delivered.

5: Comedic timing

August 2014

Gary Cotterill, the veteran Sky reporter, was outside Queen’s Park Rangers’ Loftus Road stadium, a favoured place for breaking news when Harry Redknapp was the manager: he would always lean out of the window of his Range Rover for a chat.

Cotterill had just heard that Sandro, Tottenham’s midfielder, was moving west to QPR. Back in the studio, Sky anchor Jim White became characteristically noisy when he spotted a white Rolls Royce arriving at the ground. “Something’s happening, Gary,” he yelled. And indeed something was.

Out from the back door emerged a young man loudly exclaiming that he had signed for the club. It quickly became obvious, however, this was not Sandro but the comedian Simon Brodkin, channelling his alter-ego Jason Bent, a fictitious Premier League star. Even as the interloper disturbed his broadcast insisting he really had been signed, Cotterill was not remotely fazed. Wearing the expression of someone who had seen it all, he waved his thumb at Brodkin, dismissing the prank with a curt: “Sandro is official. He isn’t.”

4: Sleeping in

January 2008

Having failed in their attempt to hijack Berbatov, Manchester City almost missed out on what seemed a much less demanding deal. They had agreed terms with Portsmouth to bring Zimbabwe international Benjani Mwaruwari north. But when it came time to conduct a medical, there was no sign of him.

It transpired Benjani had missed not one but two flights from Southampton to Manchester earlier that day, and a scheduled third had been cancelled. He eventually only made it to City’s training ground for the necessary examination with 45 minutes to spare. And the reason for the missed flights? Such was his overarching excitement at the move, the player had fallen asleep at the airport. Or so rumour had it for more than a decade. But in his autobiography Harry Redknapp (him again), then in charge at Portsmouth, revealed that the player had not wanted to go to City at all and had refused for much of the day to board the flights.

The manager had eventually been obliged physically to push him on to a plane.

3: Argentinian beef

August 2006

If not the most unexpected deadline-day deal of all time, then certainly the one with the widest ramifications, was when West Ham announced they were signing Argentina internationals Javier Mascherano and Carlos Tevez.

The pair had not come to east London out of a long-held ambition to link up with manager Alan Pardew. Indeed, they had no say in the matter, given that their registration was owned not by the club they played for – Corinthians in Sao Paulo – but by a complex network of wheeler dealers including the Israeli super-agent Pini Zahavi, the British horse-racing enthusiast Kia Joorabchian and at least two Russian oligarchs. The phrase “undisclosed fee” was doing a lot of heavy lifting in this context. But any hidden cost was going to be exacerbated down the line.

For while Mascherano was quickly dispatched up to Liverpool on loan, Tevez’s goals hugely contributed to West Ham winning seven of their last nine matches to stave off what had appeared to be certain relegation. Sensing that the signing was so full of holes it resembled a colander, Sheffield United, the club relegated in their stead, sued West Ham. In an out-of-court settlement, the Hammers paid £20 million in compensation, plus another £5 million in fines to the Premier League, who swiftly banned the practice of third-party ownership.

Meanwhile, Tevez demonstrated his loyalty to West Ham by immediately signing for Manchester United.

2: Purple pain

August 2014

This was the moment that showed quite how out of hand deadline-day reporting had become. Sky’s Alan Irwin was stationed outside Everton’s Finch Farm training ground, where he was in the middle of a piece about Tom Cleverley moving from Old Trafford. As he spoke, a prankster approached and shoved something into the reporter’s ear. What Irwin, trying to carry on with his news, could not see was that this was a vibrant-purple sex toy.

It was the culmination of a significant increase in deadline-day rowdiness as fans – often lubricated by an evening in the pub – surrounded the reporter, noisily trying to get their faces on the telly. Soon afterwards, Sky decided any potential drama was not worth compromising the safety of their staff. And from 2016, all live reporting was conducted from a safe, and less publicly accessible, spot within the training ground.

1: Car-park scramble

January 2013

This was not contrived, scripted or dreamed up by an over-imaginative comedian. It was just hilarious, if a little poignant.

Hearing on the grapevine that QPR wanted to sign him, West Bromwich Albion winger Peter Odemwingie drove down from the Black Country to west London in order to facilitate the move. He arrived at Loftus Road only to discover nobody there was expecting him. The rumour had no foundation in truth.

This, however, was not something he could keep to himself, given the Sky cameras were already in place and microphones were poised. His forlorn interview through his car window was the kind of content the broadcaster dreamed of: a comedy of errors played out live and exclusively. Odemwingie eventually left the Hawthorns for Cardiff City. He later became a professional golfer. As yet he has not been filmed arriving at the first day of the Open only to discover he has no invitation to play.