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25. Luther Blissett (Watford to Milan)
It’s long been rumoured that Milan signed Blissett by mistake, confusing him for Watford team-mate John Barnes. That almost certainly isn’t true, but it did come as a surprise when the Rossoneri identified a player who had only ever played a single top-flight season as the ideal focal point for their attack. The move didn’t work out, and Blissett was back at Vicarage Road within a year.
“No matter how much money you have here,” the striker sighed during his time at San Siro, “you can’t seem to get Rice Krispies.”
24. Ronnie O’Brien (Middlesbrough to Juventus)
Juventus have proved canny operators in the transfer market over recent years, with Aaron Ramsey following in the footsteps of fellow top-class midfielders Andrea Pirlo, Sami Khedira and Paul Pogba in moving to Turin on a free transfer.
O’Brien was a trendsetter in that regard; after being released by Middlesbrough without having played a single game for the club, the young Irishman was snapped up by Juve in 1999. He didn’t quite enjoy the same level of success as Pirlo, Khedira or Pogba, though, instead spending most of his time in Italy out on loan before sealing a permanent switch to FC Dallas in 2002.
23. Edgar Davids (free agent to Barnet)
It’s fair to say that Davids didn’t set the world alight in a curious stint at Crystal Palace in 2010: the Dutch legend made just seven appearances for the then-Championship club (most of which came at left-back) before both parties agreed to terminate his contract.
That seemed to be that for the former Ajax, Milan, Juventus and Barcelona midfielder – until League Two Barnet picked up the phone, that is. Davids played 29 games for the Bees in 2012/13 but was unable to prevent them dropping into the Conference, from where he demonstrated why most former Netherlands internationals don’t end up working as player-managers in England’s fifth tier.
22. Juninho (Sao Paulo to Middlesbrough)
‘Talented Brazilian youngster moves to Premier League’ would hardly be a story these days, but it was a big deal back in 1995 – even more so given that Juninho had been linked with a host of European giants before arriving on Teeside.
Boro had only just been promoted to the Premier League and would soon sink back to the second tier, but the pint-sized playmaker became a cult hero at the Riverside Stadium over the next two campaigns. He even returned for a second stint in 1999 and a third in 2002, despite later revealing to FourFourTwo that he used to stuff his boots with newspaper to deal with the northeast’s bitter winters.
21. Claudio Caniggia (Atalanta to Dundee)
What do you do when you’re looking for a new challenge having already won the World Cup, the Copa America and the Copa Libertadores? Why, pitch up at a Dundee side that had just finished third-bottom of the SPL, of course.
Fans of the Dee could hardly believe their luck when Diego Maradona’s former Argentina team-mate arrived at Dens Park in 2000. Unsurprisingly, Caniggia immediately became Dundee’s star player and sealed a move to Rangers after a solitary season on the club’s books.
19. Sol Campbell (Portsmouth to Notts County)
After leaving Portsmouth at the end of 2008/09, retirement seemed to beckon for former Arsenal and England centre-back Campbell. Yet Notts County, who had recently appointed Sven-Goran Eriksson as director of football following a Middle Eastern takeover, succeeded in persuading him to join the League Two outfit.
Not that the arrangement lasted long: Campbell played just 90 minutes for the Magpies before departing. "I knew I would be the club's first big signing but was told I would be the first of many," the defender huffed. "Names like Roberto Carlos and Benjani were mentioned, but nothing materialised." Funny, that.
18. Alberto Tarantini (Boca Juniors to Birmingham)
Tarantini left Boca Juniors before the 1978 World Cup in Argentina, which the hosts won with victory over the Netherlands in the final. The left-back was a man in demand following his contributions to that historic triumph, so it came as a surprise when Birmingham won the race for his signature soon after the conclusion of the competition.
17. Dale Jennings (Tranmere to Bayern Munich)
Tranmere Rovers to Bayern Munich isn't exactly one of football's most well-trodden paths, but it was the route taken by Jennings back in 2011. The Liverpool-born winger suffered a serious knee injury soon after his arrival in Germany, however, and struggled to make an impact in Bayern's reserve team upon his return.
Jennings moved back home in 2013, spending a couple of years at Barnsley before joining MK Dons ahead of the 2015/16 season. Still only 24, he's now been without a club for over 18 months.
16. Kyle Lafferty to everyone
He joined Rangers from Burnley (after the move had initially broken down), left Scotland under a cloud to play for Sion in Switzerland, alongside and then under renowned nutcase Gennaro Gattuso (once FIFA had stepped in to approve the deal), swapped Sion for Palermo in Serie B (where president Maurizio Zamparini – hardly the shy and retiring type himself – called him “an out-of-control womaniser”, “an Irishman without rules” and “completely off the rails”).
He then joined Norwich and found himself frozen out, popped over to Turkey for a loan at Caykur Rizespor and then returned to Norfolk, all while firing Northern Ireland to their first European Championship. You'll currently find him (back) at Rangers following a loan spell with Birmingham and full-time stint at Hearts. All hail the king.
15. Alejandro Sabella (River to Sheffield United)
Never has such a talented player been forgotten by posterity simply for not being Diego Maradona. Sabella was a highly-rated midfielder when second-tier Sheffield United signed him from River Plate, having been priced out over a 17-year-old Maradona. Ever since, Maradona has been the centre of that story. Sabella’s big-money arrival leaves people nonplussed now, like an American reality TV brat shrugging because her Sweet 16 present is a Porsche, not a Lexus.
Sheffield United fans didn’t feel that way. Sabella was popular and said himself: “I’m happy with my years in England.” Years later, he coached Argentina to a World Cup final. Have that, Diego.
14. Esteban Cambiasso (Inter to Leicester)
There’s no shortage of older players making random moves for a new experience or new offshore bank account – that’s why they’re not on this list. However, Cambiasso following life as an Inter regular by rocking up at newly promoted Leicester was truly unexpected.
13. Craig Davies (Oxford United to Hellas Verona)
Many wondered why Davies thought joining Verona would improve his odds of playing for Wales. The real question, surely, is why a club targeting promotion to Serie A did their shopping in the English fourth division.
Bought for £85,000 and given a five-year contract, 20-year-old Davies played one match before returning homesick to join Wolves. Meanwhile, Verona and Oxford were both relegated – everyone’s a winner.
12. Sergei Yuran (Spartak Moscow to Millwall, loan)
“Jimmy Nicholl said I was the most unprofessional player he’d ever met. That was true.”
Yuran admitted his disastrous 1996 spell with Millwall – a move seen then as equal parts exciting and unexpected – was down to partying, and that he reassured his new wife it was “the way all footballers live in England”.
You have to respect Yuran’s candidness – and that he had the guts to take liberties with Millwall, of all teams.
11. Steven Caulker (QPR to Liverpool, loan)
Jurgen Klopp signed Caulker in 2016 having last seen him in a Southampton defence ripped apart 6-1 by his Liverpool team. Naturally, he played Caulker up front in his first three matches.
To the bespectacled oddball’s credit, Caulker was instrumental in Adam Lallana’s winner during Liverpool’s mad 5-4 victory over Norwich. It harked back to Manchester City boss Stuart Pearce sticking David James up front, where he was dreadful but wrought such chaos that City won a penalty.
Klopp’s a clever man, but we can’t rule out the possibility that in Caulker he saw a man averaging a goal per game at international level and thought he was onto a winner.
10. Carlos Tevez & Javier Mascherano (MSI to West Ham)
This double transfer came out of nowhere in 2006. Yet even when West Ham paid £5.5m in fines for breaching the Premier League’s rules on signing players from third-party owners (Tevez and Mascherano played for Corinthians but ‘belonged’ to companies owned by Kia Joorabchian), they knew it bought them top-flight status.
Allegedly, Tevez was picked at his countryman’s expense, as West Ham decided they could afford match bonuses for only one and chose the guy scoring all of their goals. Thus, while Mascherano played in only five games – all of them defeats – and became back-up to Hayden Mullins, Tevez helped save the Hammers from relegation at the expense of Sheffield United, rendering Neil Warnock furious. So not all bad news.
9. Tyrone Mears (Derby to Marseille, loan)
Transfers are a simple business: you need another team to want you, and your club’s permission to go. Tyrone Mears had one of those things.
In 2008 the Derby full-back arrived at Marseille – whose interest was a surprise in itself, following Mears’ lengthy injury lay-off and the Rams’ 11-point season in the Premier League – despite being forbidden to leave. “[Marseille’s offer] is completely and utterly unacceptable,” said a Rams mouthpiece. “The chairman and the manager made it clear to the player and Marseille there would be no deal.”
8. Nicklas Bendtner (Arsenal to Juventus, loan)
No doubt Lord Bendtner felt it was justified, but his season-long loan switch to Juventus in 2012/13 puzzled most people, including Bianconeri fans. As late as March, the club admitted they hadn’t sold a single Bendtner shirt.
The Dane, who’d been with Sunderland the previous season, made a handful of substitute appearances but was included in the Italian champions’ starting XI only twice. Injuries were partly to blame, but not as much as the fact that they were Juventus and he was Nicklas Bendtner.
7. Tommy Lawton (Chelsea to Notts County)
Dressing-room discord, transfer requests and mutiny – and no, we're not talking about the Chelsea of 2015/16. No, this is Chelsea in 1947. Flying the flag for old-fashioned football, with its proper balls and preposterous transfers, is Tommy Lawton.
Notts County were managed by his friend and former Blues masseur Arthur Stollery, but the catalyst for Lawton’s request to leave Chelsea was his beef with the club hierarchy and manager. Football hasn’t changed that much in 70 years, it seems.
6. Jamie Stevenson (Alloa Athletic to Real Mallorca)
Stevenson was just a teenager on holiday when his “messing about on the sideline” of his uncle’s seven-a-side game somehow caught the eye of an extremely itinerant Iberian scout. An unlikely trial at Real Mallorca followed, as did seven goals in three under-18 matches, and finally a contract to tempt him away to the Spanish island after two appearances for Alloa.
Sadly, the midfielder didn’t make a single first-team appearance for the Spaniards and has spent the past decade fulfilling a creditable, but colder, career in Scotland’s lower leagues.
5. Papy Djilobodji (Nantes to Chelsea)
It’s no secret that the prospect of trusting an academy player fills Jose Mourinho’s heart with terror (their youth reminds him of time’s ceaseless march towards death). So when wooing Everton’s John Stones in summer 2015 finally proved fruitless, he put out a ‘help wanted’ ad pleading for someone, anyone, to be Chelsea’s fifth-choice centre-back.
Papy Djilobodji arrived for £4m having played nearly 200 games for Nantes, but his omission from Chelsea’s Champions League squad was an omen. He failed to impress in his 62 seconds of match action as a stoppage-time substitute against Walsall, and now plies his trade for Guingamp back in Ligue 1.
4. Julien Faubert (West Ham to Real Madrid, loan)
“His agent should be knighted by the Queen.” The words of Paul Merson, after the first recorded incidence of the Soccer Saturday team being shocked into silence.
Football agents speak of Faubert’s January 2009 move from West Ham to Real Madrid in hushed tones of awe. Amid two appearances for the Galacticos, the Frenchman repaid his representative by appearing to fall asleep on the subs’ bench and missing training by mistake (“He got confused,” said manager Juande Ramos, probably confused to be at the club himself). Madrid chose not to make the loan permanent.
3. Bebe (Vitoria de Guimaraes to Manchester United)
A lot of the things said about Bebe aren’t actually true. So unexpected was his 2010 arrival, British fans and journalists latched onto any rumour: that he’d played in the Homeless World Cup (he hadn’t); that Manchester United paid £7m to a tiny team (the fee went to top-five team Vitoria and third-party owners); that even now Bebe compares himself to Cristiano Ronaldo (he merely said Ronaldo is one of his idols, and they share shooting and running styles).
For all that, splashing out on a 20-year-old, despite claiming not to have seen him play, was Alex Ferguson’s most baffling decision.
2. Allan Simonsen (Barcelona to Charlton)
Charlton fans are unhappy at their current owner’s dealings. Their protests have merit. We wouldn’t be surprised, though, if a couple of them are disillusioned that they’re no longer bringing in European trophy winners.
Allan Simonsen had just scored the goal that brought Barcelona their biggest continental crown thus far, the Cup Winners’ Cup, when they signed Diego Maradona – making Simonsen a surplus overseas player and therefore destined for the exit.
Quite why Second Division Charlton were top of a list headed Literally Anywhere That Isn’t Barcelona is anyone’s guess, but Simonsen once claimed it was because he wanted a quiet life.
1. Kevin Keegan (Hamburg to Southampton)
Today, swapping Hamburg for Southampton would represent a step up, but not in February 1980: Hamburg were defending their Bundesliga title while Saints were re-establishing themselves in the top flight. Keegan, meanwhile, had won his second consecutive Ballon d’Or with the German club six weeks earlier.
