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55 shocking football transfers that shook the world: 55-41

How many of our most shocking football transfers do you remember? And what was the real story behind the switch? Read on as we chart the deals that almost broke the game.

First, a couple of caveats: we've tried to include a fair range of transfers from every time period, and where some transfer fees were not disclosed, we've gone for the most often cited (if disclosed). We've also converted them to pounds sterling. As ever, tell us what we got right or wrong in the comments below, on Facebook, or on Twitter.

Words: Andy Murray, Harriet Drudge, Chris Flanagan, Gregor MacGregor, Joe Brewin, Jon Spurling, Marcus Alves, Greg Lea, Alex Hess, Seb Stafford-Bloor

55. Ronaldinho (Milan to Flamengo, 2011)

Fee: Undisclosed
It was 2011, and Ronaldinho Gaúcho was sick and tired of Massimiliano Allegri at Milan, so he asked his brother and agent Roberto de Assis to find a club in Brazil after 10 years far from home.

Palmeiras, Grêmio and Flamengo were all interested in the five-time world champion (as were Blackburn), and each had to face a soap opera-style saga that had most of its scenes set in a Rio de Janeiro steak house.

Palmeiras had coach Big Phil talk to Assis and convince him of the deal, while Grêmio put speakers on the stadium’s pitch to celebrate with the fans after claiming to have had Ronaldinho's comeback confirmed. In the end, though, the Brazilian ace signed for Flamengo. Saga over. MA

54. Andrea Pirlo (Inter to Milan, 2001)

Fee: Part exchange
While it may now seem odd, Andrea Pirlo should actually have been an Inter legend. The Nerazzurri signed him from Brescia in 1998, back when he didn’t have a beard and played as a No.10. A brief loan spell back with his former club proved the making of him, however, with coach Carlo Mazzone being the first to deploy him as the deep-lying playmaker he became.

That caught the attention of Carlo Ancelotti and Milan, who somehow convinced Inter to part with Pirlo in exchange for €2.8m and average Argentine Andres Guglielminpietro. They would repeat the feat by taking Clarence Seedorf from their neighbours in a straight swap for Francesco Coco. Pirlo won two Scudetti and two Champions League titles before moving to Juventus for free in 2011 – another shockingly good value deal for the Italian schemer. AD

53. Paul Pogba (Juventus to Man United, 2016)

Fee: £89m
There always seems to be at least one long-running saga dominating during the summer transfer window. In 2016 it was the ‘Paul Pogba: will-he-won’t-he’ drama that resulted in Manchester United paying a world-record fee – £89m and then some in add-ons – for a player they let leave for free in 2012.

When he departed United for Juventus as a 19-year-old, Pogba told team-mate Rio Ferdinand it was to become the best player in the world. He needed playing time that he wasn’t guaranteed under Sir Alex Ferguson at Old Trafford, with Paul Scholes, Michael Carrick and even Anderson getting the nod ahead of him.

Fast-forward four years, with four Serie A titles, two Coppa Italia and two Supercoppa Italiana trophies to his name: #POGBACK is trending on Twitter, as the France international announces his shock return to the club he says is his home. HD

52. Carlos Gamarra (Palmeiras to Olimpia, 2007)

Fee: £1.7m
Carlos Gamarra didn't concede a single foul in the 1998 World Cup campaign that almost saw Paraguay beat hosts France. Much later on his career he could have had his pick of clubs after a fine career in Europe with the likes of Inter, Benfica and Atletico Madrid – but anyone but Olimpia.

Well, according to Cerro Porteño fans anyway – the club he'd began his career with in 1990, and where he became an idol after winning two Paraguayan titles. So when he returned home in 2007, it was expected that Gamarra would announce one final move to end his career at Cerro.

He'd probably wished he did. Instead, the stopper ended up signing for rivals Olimpia, and felt the supporters’ wrath so badly that they tried to set his house on fire. MA

51. Cafu (Zaragoza to Palmeiras, 1995)

Fee: Undisclosed
São Paulo and Palmeiras’s training grounds are separated by a wall in the Barra Funda neighborhood. The rivals have never had a great relationship and, among others, you can blame former right-sided defender Cafu for it.

The two-time world champion won everything with São Paulo at the beginning of the '90s and was sold to Zaragoza in 1994, with a special clause saying that the Spanish side would have to pay the additional amount of US$3.6 million if they sold Cafu to Palmeiras before 1996.

Back then, Palmeiras had milk company Parmalat as a heavyweight sponsor and somehow found a way to sign Cafu by using a smaller team, Juventude, who were also partners of the nine-time Brazilain champions. The right-back spent only a month at the satellite team, and is still hated by São Paulo’s fans. MA

50. Colin Kazim-Richards (Fenerbahce to Galatasaray, 2011)

Fee: Free
"I’m from east London, E17. Where I grew up you’d got a problem going to E11 – it was life-threatening," Colin Kazim-Richards declared to FourFourTwo in November. "So moving clubs… no one was going to kill me. That’s what I was thinking at the time."

Nobody needs reminding of the vitriol between Fenerbahce and Galatasary supporters, but it didn't faze daring globetrotter Kazim-Richards, who crossed the scorched divide on a free transfer in January 2011. The ex-Bury forward had spent three-and-half productive years with the Yellow Canaries, with whom he made his Champions League debut and won the majority of his Turkey caps, but soon became a victim of the country's madcap press and eventually had his contract terminated.

Two days later he'd skipped across the Bosphorus. "I’d have been stupid not to go," Kazim-Richards told FFT. "I wanted to work with Gheorghe Hagi, an all-time great footballer. Tugay (ex-Blackburn) called me and said, ‘Listen, are you up for it? I know it’ll be hard moving here from there’. It took me two seconds. I said, ‘Yeah, let’s do it’."

He didn't take too long to endear himself to a sceptical new set of fans, though – on debut he netted the last-ever goal at Ali Sami Yen Stadium, then bagged the first goal in the first-ever derby at Türk Telekom Arena against Fenerbahce. JB

49. Roy Keane (Nott'm Forest to Man United, 1993)

Fee: £3.75m 
One Friday in June 1993, Kenny Dalglish went into the weekend thinking he had his man. The Blackburn Rovers manager had just shaken hands on personal terms with Roy Keane for a British record £4m transfer from relegated Nottingham Forest, but the Ewood Park office had already closed. No harm done, thought Dalglish – the paperwork would be finalised first thing Monday morning. Over the weekend, Keane’s phone rang.

“Roy, it’s Alex Ferguson. Have you signed any forms?” asked the Manchester United manager. Keane confirmed he hadn’t. “Why don’t you come to Manchester and have a chat with me before you do anything?”

Over a game of snooker, Ferguson convinced Keane to reject Dalglish in favour of Old Trafford. “Nobody does this to Kenny Dalglish,” third-personned the Rovers boss when Keane informed him of his change of heart. “You’re a wee bastard and you won’t get away with this.”

Seven Premier League titles later, he probably did. AM

48. Paul Gascoigne (Newcastle to Tottenham, 1988) 

Fee: £2.2m
After receiving a verbal assurance from Newcastle’s Paul Gascoigne in July 1988 that he’d be joining Manchester United imminently, the Red Devils boss disappeared to enjoy a relaxing holiday, only to discover shortly after arriving that Gazza had instead joined Tottenham for a British record £2.2 million fee (a scenario to be later reversed with Keane).

The reason? The north London club had offered his parents a house and a car, and his sister a sunbed. Despite winning the FA Cup in N17, Gazza later admitted that perhaps his career would have taken a different trajectory at Old Trafford. Fergie’s holiday was ruined, but at least Gazza’s sister got a nice suntan.

The United boss, meanwhile, later remarked about what might have happened had Gazza come under his stewardship, telling the Telegraph: "Alan Shearer is one [player] I wish I'd signed, but for me the most disappointing of all was Paul Gascoigne. I think it was a bad mistake, and Paul admits it. We had Bryan Robson, a Geordie; Steve Bruce, a Geordie; Gary Pallister, from Middlesbrough... we had a structure of players who could have helped him and it could have given him some discipline." JS

47. Gareth Bale (Tottenham to Real Madrid, 2013)

Fee: £86m

With Gareth Bale smashing in 21 league goals during the 2012/13 season, including stunning solo efforts against Norwich and West Ham, the press were full of speculation about a move to Europe in the summer transfer window.

The strapping Welshman won the PFA Player's Player of the Year award for the season, plus the Young Player of the Year gong and, shortly after, the Football Writer's Award too. The obstinate Daniel Levy had everything he needed to exact the full value from Tottenham's most sellable asset, with Champions League qualification eluding the Lilywhites. Rumours of a move to Real Madrid began to grow across the summer months, with talk of a world-record fee in the offing.

When Spurs then lavished some £105 million on the likes of Vlad Chiriches, Nacer Chadli and others, the game was up: this splurge needed balancing and a £86m fee would tidy up the balance sheet nicely. Levy and Florentino Perez squabbled over clauses and sell-on fees, but eventually Carlo Ancelotti got his man and Cristiano Ronaldo had been replaced as the most expensive player in the world. Unless you lived in Madrid that is, where – with the fee undisclosed – it was played down to keep the Portuguese superstar's ego suitably soothed. GM

46. Alan Shearer (Blackburn to Newcastle, 1996)

Fee: £15m
That Shearer left Blackburn, a year after helping them to the Premier League title and weeks after starring at Euro 96, wasn't totally unexpected. But it was the sheer scale of the transfer that made headlines – a world record £15m fee, with 15,000 Newcastle fans turning up at St James' Park just to greet him.

Blackburn's attempts to persuade him to stay included Jack Walker surprisingly offering him the manager's job at Ewood Park aged 25, but Shearer politely declined that offer and the interest of reigning champions Manchester United to join his boyhood club.

Newcastle were hesitating on the fee until their Magpies-supporting bank manager stepped in and offered to find a way of funding the deal, such was his desire to see Shearer play for the Toon. CF

45. Andy Carroll (Newcastle to Liverpool, 2011)

Fee: £35m
"It is about control. We had the control. We knew the Torres deal was there. We drew that f***ing deal, perhaps the ultimate. So £30m? F*** off! Don’t waste my time. I slammed the phone down. £35m? Everybody including Pardew (then Newcastle manager) all agreed.

"But the £35m they wanted to pay over four years. It was rubbish. Mike (Ashley) said – and he is a brave boy, Mike, I promise you – get all the £35m up front."

That was Derek Llambias's version of events on January 31, 2011. He had a habit of a making himself the hero of most anecdotes, so it should perhaps be treated with scepticism. Still, Carroll did move for £35m and what happened next was a relative disaster: a succession of injuries, a critical change in management and style, and a Liverpool career which comprised just 11 goals.

As you suspect will likely be the case upon his retirement from football, this was very much a case of what might have been. SSB

44. Johan Cruyff (Ajax to Barcelona, 1973)

Fee: £922,000
“Get me out of here,” Johan Cruyff instructed his father-in-law and representative Cor Coster after losing out on the Ajax captaincy in summer 1973. Events moved rapidly, and for a hefty 60 million peseta fee, Cruyff headed to Barcelona after rejecting a move to Real Madrid because it was a “fascist club”.

The whole transfer was highly political, with the Dutch Football Federation threatening to block the deal, and Cruyff vowing to boycott the 1974 World Cup if the Federation didn’t sanction the move. Grudgingly they did, and Cruyff quickly became a Catalan icon. JS

43. Jaap Stam (Man United to Lazio, 2001)

Fee: £15.3m
It’s safe to say Sir Alex Ferguson got most things right during his trophy-laden 26 years as Manchester United manager, but the Scot has frequently expressed regret at his decision to sanction Stam’s departure in 2001.

Ferguson always insisted that the sale of the centre-back had nothing to do with critical comments made in his autobiography, but it’s hard to see how the deal made any sense from a purely footballing point of view. One theory purported (by journalist Simon Kuper among others) was that the Dutchman became an early victim to poorly applied data analysis in football – in particular, that Stam was discarded because he was making fewer tackles towards the end of his Manchester United career. It was later, in fact, found instead to be because the defender was reading the game better than ever and positioning himself to intercept the ball more rather than have to make a one-on-one challenge.  

No wonder that Stam went on to excel in Serie A, first with Lazio and then Milan, before retiring after a single season at Ajax in 2006/07. GL

42. Juninho Paulista (Sao Paulo to Middlesbrough, 1995)

Fee: £4.75m
The brilliant diminutive Brazilian playmaker switched to Boro back in the mid-'90s, becoming the most successful signing of Bryan Robson's newly promoted Riverside outfit.

Tracked by several top European clubs, the Sao Paulo attacking midfielder had just made his breakthrough with the Brazil senior team that February and already won the Copa Libertadores and Intercontinental Cup by the time he moved to England. Then only 22, he immediately set pulses racing with his magnetic ball control and surges forward from midfield.

Two seasons of top-flight English football culminated in two losing finals (League and FA Cup), relegation and a subsequent move to Atletico Madrid for £13m at a healthy profit. However, the cult hero returned twice more to the north-east, on loan to help the promoted Boro in 1999 before joining up with the Teesiders again in 2002, helping them to win the League Cup in 2004. GM

41. Andreas Moller (Borussia Dortmund to Schalke, 2000)

Fee: Free
Not only did this transfer upset Borussia Dortmund fans, it also aggravated Schalke's too. Moller had already irritated Dortmund supporters by leaving for Eintracht Frankfurt in 1990, only to return for a second spell in which he re-established himself as a hero and helped BVB to Champions League glory in 1997.

Three years later he was off again: this time to Dortmund's fierce local rivals Schalke following the expiry of his contract. Dortmund fans were livid, and Schalke's didn't exactly welcome the arrival of a man they'd previously grown to hate. Awkward... CF

55-41 • 40-31 • 30-21 • 20-11 • 10-1

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