The transfer window sometimes overshadows the actual football these days, but the following deals understandably made everyone sit up and take notice.
Presenting the 32 most shocking transfers in the history of the game…
32. Al-Saddi Gaddafi, Al-Ittihad Tripoli to Perugia
The son of the then-Libyan dictator Muammar Gaddafi, Al-Saddi owed his role as captain of the national team to nepotism. Having previously been rejected by a Maltese club, Gaddafi was snapped up by Perugia to all-round astonishment.
Despite hiring Diego Maradona and the Canadian sprinter Ben Johnson as advisers, Gaddafi was woefully out of his depth in Serie A.
31. Attilio Lombardo, Juventus to Crystal Palace
The Italian was a cut above anything else the Eagles had to offer. But Palace finished bottom and Lombardo bizarrely spent seven weeks as caretaker player-manager.
30. Samuel Eto'o, Inter to Anzhi Makhachkala
From Colombia in the 1950s to Saudi Arabia in the 2020s, players have always been tempted by lucrative offers from countries outside the footballing elite.
And so it proved when Anzhi Makhachkala, a club that even many Russians hadn’t heard of, made Eto’o the highest-paid player in the world in 2011.
29. Thomas Gravesen, Everton to Real Madrid
Given their enactment of a galactico recruitment policy which targeted high-profile superstars like Zinedine Zidane, Ronaldo and David Beckham, Real Madrid’s signing of Gravesen stood out.
The unfashionable ball-winning midfielder left Everton for the Spanish capital in January 2005, just days after he’d played against Plymouth in the FA Cup.
28. Jay-Jay Okocha, PSG to Bolton
During his time at PSG, a young talent by the name of Ronaldinho looked up to Okocha. When the Nigerian sought pastures new in 2002, few expected him to pen a deal with Bolton.
Okocha was a major hit at the Reebok Stadium, where he remained for four seasons. He was later voted Bolton’s greatest ever player.
27. Ashley Cole, Arsenal to Chelsea
In an all-advised passage, Cole wrote in his autobiography that Arsenal’s offer of a new contract worth £55,000 per week left him “trembling with anger”.
26. Lionel Messi, Barcelona to PSG
Despite rumours of a romantic return to Newell’s Old Boys, it seemed inevitable that Messi would finish his career having only played for Barcelona.
But that was until the money ran out. The cash-strapped Catalans could no longer afford Messi’s gargantuan wages by 2021, paving the way for a switch to PSG on a free transfer.
25. Mario Gotze, Borussia Dortmund to Bayern Munich
Dortmund had won two of the previous three Bundesliga titles when Gotze agreed to cross the divide, just a month before the teams met in the 2013 Champions League final.
24. Juninho, Sao Paulo to Middlesbrough
Sao Paulo to Middlesbrough isn’t exactly a well-trodden path, but it’s the one that Juninho took in the mid-1990s.
Despite interest from larger European clubs, the diminutive Brazilian joined the Premier League new boys for £4.75m. He was a major hit and went on to have three spells with the Teesiders.
23. Gabriel Batistuta, River Plate to Boca Juniors
River Plate and Boca Juniors share perhaps the fiercest rivalry in world football, but that didn’t deter Batistuta from joining the latter from the former in 1990.
Batisuta hinted that he would have stayed at River had it not been for their manager Daniel Passarella, who dropped him from the team in the middle of the campaign.
22. Tommy Lawton, Chelsea to Notts County
In 1946/47, Tommy Lawton scored 26 goals for top-flight Chelsea. Picture the reaction, then, when the striker bade farewell to Stamford Bridge in order to sign for Notts County in the Third Division South.
Lawton made the move because he wanted to reunite with Arthur Stollery, a former trainer at Chelsea who became manager of Notts County.
21. Julian Faubert, West Ham to Real Madrid
“His agent should be knighted by the Queen,” said a flabbergasted Paul Merson when news of Faubert’s loan move to Real Madrid reached the Soccer Saturday studio in January 2009.
20. David Beckham, Real Madrid to LA Galaxy
Major League Soccer was founded in 1993 but virtually no world-famous stars plied their trade there before 2007. That was the year Beckham announced that he would be leaving Real Madrid for LA Galaxy.
19. Andreas Moller, Borussia Dortmund to Schalke
There’s no love lost between Borussia Dortmund and Schalke, as Moller experienced first-hand during his eight and a half years with BVB.
To say the attacking midfielder’s move to Schalke in 2000 was unexpected would be an understatement. Worst of all, Dortmund didn’t get a penny due to Moller’s status as a free agent.
18. Robin van Persie, Arsenal to Manchester United
After a strong second half of the season in 2011/12, Arsenal hoped to mount a Premier League title tilt the following year. What they didn’t countenance was club captain Van Persie joining Manchester United.
The Dutchman’s goals fired Alex Ferguson’s side to title glory in 2012/13, leaving Arsenal to rue what might have been.
17. Cristiano Ronaldo, Real Madrid to Juventus
Cristiano Ronaldo sent shockwaves through the footballing world when he chose to leave Real Madrid, who had just won three consecutive Champions Leagues, for Juventus in 2018.
Ronaldo had previously asserted that he wanted to finish his career in the Spanish capital, but the Portuguese then claimed that he no longer felt sufficiently valued by Madrid president Florentino Perez.
16. Carlos Tevez, Manchester United to Manchester City
Due to his complicated third-party ownership, Tevez joined Manchester United on a two-year loan in 2007. “Fergie, sign him up,” sang the Old Trafford faithful towards the end of the arrangement.
Instead Tevez hot-footed it across town to Manchester City, signing a five-year deal. “Alex [Ferguson] never called me or sent me any text messages,” the Argentine huffed.
15. Johan Cruyff, Ajax to Feyenoord
Ajax’s greatest ever player lifted 18 trophies - including three European Cups - and won three Ballons d’Or across two spells in Amsterdam.
But when Ajax opted against offering the 36-year-old a new deal in 1983, he had no qualms about joining arch-rivals Feyenoord. Almost to prove his point, Cruyff promptly won a league and cup double at De Kuip, then retired.
14. Fernando Torres, Liverpool to Chelsea
The warning signs had been there towards the end of his time at Liverpool, but that didn’t stop Chelsea splurging £50m on Torres in January 2011.
It must have been tough for the Reds to sell the striker to a direct rival, but they swallowed their pride to do a deal which made business sense.
13. Robinho, Real Madrid to Manchester City
Manchester City announced themselves as a major force in European football when they signed Robinho from Real Madrid on 1 September 2008, the same day the club was bought by the Abu Dhabi United Group.
The Brazilian thought he was joining Chelsea, only to learn at the last minute that his actual destination was Manchester.
12. Allan Simonsen, Barcelona to Charlton
Simonsen’s last game for Barcelona saw him score the winning goal in the 1982 Cup Winners’ Cup final. But the Dane was then forced out of the Camp Nou due to restrictions on foreign players which saw Barca favour the incoming Diego Maradona.
Simonsen received offers from Tottenham and Real Madrid but somehow ended up at Second Division side Charlton.
11. Mo Johnston, Nantes to Rangers
In the early 20th century Rangers enacted a policy which stated they would not sign any Catholic footballers. This convention was shattered when Graeme Souness brought Johnston to Ibrox in 1989.
The deal was even more shocking as the former Celtic striker had publicly revealed that he was set to rejoin the Hoops, only to change his mind.
10. Ricky Villa and Ossie Ardiles, Racing Club and Huracan to Tottenham
English clubs simply didn’t sign Argentina internationals back in 1978, so the arrival of Villa and Ardiles in north London was a seismic event.
The pair became club legends even amid the hostilities between Britain and Argentina, who fought a 10-week war over the Falkland Islands in 1982. Ardiles stayed at White Hart Lane for a decade.
9. Andy Cole, Newcastle to Manchester United
Newcastle were Manchester United’s closest Premier League challengers between 1995 and 1997, despite selling their star player to Alex Ferguson’s side at the start of that period.
Newcastle boss Kevin Keegan was forced to justify his decision to sanction Cole’s departure - a deal that was shrouded in secrecy - to bemused supporters outside St James’ Park.
8. Luther Blissett, Watford to AC Milan
The rumour that AC Milan confused Blissett for John Barnes is almost certainly untrue, but the former Watford striker struggled to adapt to life in Italy - on and off the pitch - after this unexpected transfer.
“No matter how much money you have here," Blissett sighed, "you can't seem to get Rice Krispies.”
7. Kevin Keegan, Hamburg to Southampton
A two-time Ballon d’Or winner at Hamburg, Keegan decided he wanted to return to England in 1980.
Liverpool were more than happy with Kenny Dalglish, ruling out a return to his former club. Still, few imagined Keegan would join a Southampton side that had never even finished in the top five of the First Division.
6. Roberto Baggio, Fiorentina to Juventus
Not content with beating Fiorentina in the 1990 UEFA Cup final, Juventus rubbed salt in the wound by prising Baggio away from the Stadio Artemio Franchi
The legendary Italian didn’t want to leave la Viola. On his first return to the Franchi, he refused to take a penalty and then accepted a home fan’s offer of a Fiorentina scarf.
5. Eric Cantona, Leeds to Manchester United
English football could have taken a very different course had Alex Ferguson signed his first-choice striker, David Hirst, in 1992.
4. Carlos Tevez and Javier Mascherano, Corinthians to West Ham
A pair of South American superstars who had their pick of European giants inexplicably chose West Ham in 2006.
Tevez and Mascherano’s registration belonged not to Brazilian club Corinthians but to two third parties, Global Soccer Agencies and Media Sports Investments. West Ham were later fined £5.5m, but only after Tevez’s goals had kept them up.
3. Neymar, Barcelona to PSG
Spanish law dictates that every footballer must have a buyout clause in their contract. Many clubs set the figures prohibitively high to deter interest in their assets. That is what Barcelona did when they made Neymar’s worth £198m.
No bother, said PSG, who stunned the football world when they smashed the all-time transfer record in 2017.
2. Sol Campbell, Tottenham to Arsenal
When Arsenal called a press conference in summer 2001, they were expected to unveil Richard Wright. Journalists’ jaws promptly dropped to the floor when Sol Campbell, the captain of arch-rivals Tottenham Hotspur, walked through the door.
The centre-back went on to win two Premier League titles and three FA Cups at Arsenal, but he was never forgiven by Spurs supporters.
1. Luis Figo, Barcelona to Real Madrid
Figo was not the first or last player to move directly between Barcelona and Real Madrid. But his transfer in 2000 was the most shocking of all time.
Figo was a jewel in the Barcelona crown. Yet Madrid convinced him to cross the Clasico divide, resulting in the Portuguese having a pig’s head thrown at him at the Camp Nou.
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