We’ve trawled through four decades of tabloid archives and ghost-written autobiographies to find the mouth-watering (and occasionally outrageous) British-Italian transfers that could have re-shaped the face of football.
By the turn of the millennium, the domestic game in England had accelerated through the gears, powered by seemingly exponential television revenues and vanity investments by wealthy owners. This was the decade where the Premier League finally caught, and then swiftly overtook Serie A as a go-to destination for the world’s best players. Moreover, where British stars were looking to test themselves abroad, they were increasingly looking to Spain rather Italy.
The most significant British-Italian transfer came right at the end of the decade when an ageing David Beckham spent the early part of 2009 in the red and black of AC Milan. Tellingly, Beckham had already tried his hand in Spain before entering lucrative semi-retirement in the MLS. His off-season spell in Italy at the age of 36 proved surprisingly successful, and sufficiently so to be repeated the following winter.
More generally, the volume of British players moving to Italy had receded to a mere trickle. In 2003, Perugia signed a 21-year-old Jay Bothroyd from Coventry; with just fourteen career goals to his name at that point, it was hardly a transfer to set pulses racing. There were also the curiosities of Craig Davies’ stint at Verona and Kris Thackray’s move to Serie B Reggina; the former plucked from the basement of the Football League and the latter having been spotted playing for the British College’s team.
But that’s enough about the transfers that did get over the line, we’re concerned with the ones that didn’t…
Roy Keane – Manchester United to Juventus 2000
Roy Keane put in a career-defining performance against Juventus in the Champions League semi-final in 1999. Manchester United found themselves two goals down within 11 minutes in the second leg and seemingly heading for the exit door. It was their captain Keane who took the game by the scruff of its neck, first pulling a goal back and then driving the team onwards with eye-bulging intensity. As United progressed that night, against all odds, Keane cemented his place in United folklore.
Keane’s contract was due to expire in the summer of 2000 and he was stalling on a new deal. With that Turin performance fresh in the mind, Carlo Ancelotti’s Juventus were one of the clubs on red alert. Alongside Edgar Davids, Keane would have formed the base of a formidable midfield triangle headed by Zinedine Zidane. Ultimately, Keane signed a new four-year deal at United, though he continued to be coveted by Juventus who tried once again to secure his services when he next got around the negotiating table in 2003.
Les Ferdinand – Tottenham to Brescia 2001
Following his £6 million move to North London, a spate of injuries meant Ferdinand had struggled to replicate the devastating goal-scoring form he’d shown with both Newcastle and QPR. Now 34 years-old and with his contract due to expire in the summer of 2001, he began to exercise his right to speak to other clubs. Despite remaining part of David Pleat’s plans, in January, Ferdinand travelled to northern Italy to meet with representatives from Brescia.
Newly-promoted Brescia were embroiled in a battle for Serie A survival, and were desperately seeking reinforcements. They were eying Ferdinand as an alternative to Dario Hubner, who had been manfully shouldering the goal-scoring burden alongside Roberto Baggio. Spurs began to make contingency plans by opening talks with Luca Toni, a then 23-year-old forward, who was having an impressive debut Serie A campaign with Vicenza. However, the chain of transfers could not be completed in the January window and Brescia instead took Andrea Pirlo on loan, who inspired them to survival with a margin to spare.
Michael Owen – Liverpool to Lazio 2001
In 2001, Owen was rightly regarded as one of the hottest properties in European football. At 22 years of age, he had four full seasons of football and a World Cup under his belt. It would have taken a world record transfer fee of £50 million to prise him away from Merseyside – but Liverpool weren’t looking to sell. Of course, that didn’t prevent Lazio president Sergio Cragnotti from airing his desires: “I want Owen. He is a player I would have liked to have had at Lazio for some time now. Owen has the talent of an absolute champion”.
Lazio were at the top of their game, having won the scudetto in 2000 under Sven Goran Eriksson. Their interest in Owen wasn’t a flight of fancy; they were involved in some of the biggest transfers of the summer in 2001, which saw Pavel Nedved and Juan Sebastien Veron leave to be replaced by Gaizka Mendieta and Jaap Stam. Owen would have joined an impressive forward line that already comprised Marcelo Salas and Hernan Crespo. Unfortunately for Lazio, 2000 proved to be their high-water mark as financial reality caught up with them and aspirations were adapted accordingly.
Ryan Giggs – Manchester United to Inter 2003
In the early part of the decade, Manchester United were struggling to hit the heights of their historic 1999 treble season. There was an emerging sense that Alex Ferguson’s “Class of ’92” team might be coming to the end of its cycle. As David Beckham departed for Real Madrid, Inter sensed it might be their moment to land Giggs, who had been a long term target for the nerazzurri.
Inter themselves were in the midst of a trophy drought and the expected rebuild under Hector Cuper had not materialised, despite heavy investment. Inter had been a merry-go-round of top talent with the likes of Ronaldo, Clarence Seedorf and Hernan Crespo leaving and Adriano and Fabio Cannavaro arriving within a two-year window. By Giggs’ own admission this was the closest he came to leaving Old Trafford.
The formula finally began to click for Inter with the arrival of Roberto Mancini as coach in 2004. At 30 years of age, Giggs had begun to adapt his game in line with his evolving physicality and there is no reason to think he couldn’t have played a key role in Inter’s success during the latter part of the decade.
Sol Campbell – Arsenal to Juventus 2004
In the summer of 2004, Arsenal had just completed their “Invincibles” season. Understandably, their leading lights were attracting admiring glances from across the continent. One of those was a 30-year-old Sol Campbell, who was about to enter the final year of his contract at Arsenal. Campbell had previously come close to joining Inter in 2001, when his contract ran down at Spurs, when elected to join Arsenal instead.
Around this time, Juventus had just missed out on the chance to make it three consecutive scudetti. The club were in a rebuilding phase; Fabio Capello had been brought in to succeed Marcello Lippi and the Agnelli family were backing him in the transfer market, most notably in luring Zlatan Ibrahimovic from Ajax. Juventus were willing to offer Lilian Thuram and Stephen Appiah in exchange for Campbell – but it wasn’t to be. Naturally, Juventus had other irons in the fire that summer and instead opted for Fabio Cannavaro from Inter.
Matthew Upson – West Ham to Fiorentina 2009
Matthew Upson was bought by Arsenal at the age of 18 for £2 million, where he was groomed to become a long-term successor to Tony Adams at the heart of the Gunners’ defence. However, besieged by injury, things didn’t quite work at Highbury, and the player left to rebuild his career at Birmingham City and then West Ham. By the end of the decade he had come full circle as an England regular under Fabio Capello, proving himself to be a more than capable understudy to John Terry and Rio Ferdinand.
Meanwhile, Cesare Prandelli had quietly been creating a work of art in Florence. He had guided Fiorentina to consecutive top four finishes with a refreshing brand of attacking football. As the club prepared for an assault on the Champions League in 2009/10 they sought to bring in additional depth to their defensive ranks, and targeted Upson as their man. West Ham had an agreement with Upson that he could leave if there was interest from a Champions League team, but despite La Viola’s initial interest, a formal bid never arrived. Characteristically, Prandelli instead opted to invest his limited resources into more attacking options.
Thanks for reading – check out the 1980s and 1990s editions here, and keep checking back as we look at the British-Italian transfers that never happened from the 2010s.
Calcio England 
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