With the Manchester City captain set to join the Rossoneri on loan, GOAL evaluates all eight of his compatriots' stints at San Siro
Kyle Walker is on his way to AC Milan, with the Manchester City captain set to join the Rossoneri on loan until the end of the season with a view to a permanent switch to San Siro.
The 34-year-old's eagerness to leave the Etihad Stadium midway through the season raised plenty of eyebrows in England, but his move to San Siro has also sparked a lot of discussion in Italy. Indeed, plenty of pundits are unsure if Walker will prove a shrewd signing for Milan, given the veteran defender performed poorly for his country at Euro 2024 and struggled badly at City during the first half of the 2024-25 campaign.
Still, Walker shouldn't struggle to settle at San Siro, which is presently home to three of his compatriots, while five other Englishmen have represented the Rossoneri in the past, although, as GOAL outlines below, some spells went better than others…
Hulton Archive8Luther Blissett
Luther Blissett is quite simply one of the most infamous and influential signings in the history of Italian football, a transfer flop that became something of a counter-cultural icon.
The likeable Jamaican-born England international arrived at Milan in 1984 on the back of a wonderful season at Graham Taylor's Watford, with the Rossoneri agreeing to pay £1 million ($1.23m) for an imposing No.9 who had just finished as the top scorer in England's top flight, with 27 goals.
However, Blissett scored just five times in 30 appearances during his one and only season at San Siro before being sold back to Watford – and at just over half the price.
His legend lives on, though, as Blissett's name became a popular nom de plume among radicals, activists and artists in Italy during the mid-1990s. The forward even got in on the joke himself by later claiming on an episode of the popular British TV show 'Fantasy Football' to be part of the 'Luther Blissett Project'!
So, while Blissett's time at Milan was by no means memorable from a sporting perspective, he certainly made an impact from a cultural point of view.
AdvertisementHulton Archive7Jimmy Greaves
Jimmy Greaves scored nine goals in 10 Serie A appearances for Milan – and yet his time at San Siro was an absolute disaster. The prolific England international would even later claim in his autobiography that the transfer was the cause of his alcoholism.
It was certainly an ill-advised move. Greaves hadn't even wanted to leave Chelsea in the first place, and tried but failed to get out of the deal. Unsurprisingly, things just got worse from there, with Greaves quickly falling out with the Rossoneri's notoriously strict coach Nereo Rocco, who was renowned for keeping a very close eye on his players' private lives.
Greaves, who was only 21 at the time, said that Rocco made his life "hell" even though he was scoring freely on the field. A parting of the ways became inevitable and Greaves was sold to Tottenham in December 1961 – just six months after joining Milan.
Neither party regretted the break-up, as Greaves fired Spurs to FA Cup in May of the following year, while Milan won the league that same summer thanks in no small part to Dino Sani, the Brazilian playmaker that the Rossoneri brought on board just before getting rid of their unsettled English striker.
Getty Images Sport6Tammy Abraham
Tammy Abraham only joined Milan on loan from Roma just before the close of the 2024 summer transfer window – so it's still a little too early for a definitive judgement on his spell at San Siro.
It's certainly been eventful, though, with Abraham causing all sorts of controversy in October by missing a spot-kick against Fiorentina that should have been taken by Christian Pulisic, before netting a dramatic late winner in the shock Supercoppa Italiana win over Inter earlier this month.
The hope is that Abraham can now kick on in the second half of the season, but doubts remain over his ability to get back to his very best form, as he's not looked quite the same player since his sensational debut season at the Stadio Olimpico, with an ACL injury in June 2023 having played a big part in his struggles.
Getty Images5Rubens Loftus-Cheek
Unsurprisingly, Fikayo Tomori played a key role in Ruben Loftus-Cheek's decision to move to Milan. The pair had been team-mates at Chelsea and the defender spoke glowingly of the club, which effectively sealed the deal as far as Loftus-Cheek was concerned, as he'd also already enjoyed an encouraging chat with then-coach Stefano Pioli.
However, while Loftus Cheek's first year at San Siro went very well indeed – he equalled his career-high tally of 10 goals in all competitions over the course of a single season – he has struggled during the 2024-25 campaign.
Pioli's departure certainly didn't help, but the main issue has been injuries, which were so often a problem during the versatile midfielder's time at Stamford Bridge. The next few months, then, will determine if Loftus-Cheek can once again become a key player for Milan under new coach Sergio Conceicao.
