Since the summer of 2022, 19 players have permanently exchanged the "watery" tomatoes of England for the "bellissimo" taste-filled delights of Italy's pomodori. Scott McTominay's April interview with The Athletic detailed many great off pitch perks that he has enjoyed since his move to Napoli last summer - the standard of the tomatoes included.

In the three summer windows prior to 2022, only ten players made that same move from the Premier League to the Serie A. Granted, some of these transfers were high profile: Chelsea's sale of Tammy Abraham and Fikayo Tomori in 2021/22 and Romelu Lukaku's £62 million Manchester United exit chief among them.

Yet for the number of players making the England-Italy flight across the Mediterranean to nearly double in the past three seasons, there is surely a reason beyond the tomatoes and the weather. And through examining the range of players who have made the switch since 2019, there are a few clear categories that emerge.

Safe Haven

As much as Italy's allure of multiple football giants and extensive history can attract some of England's most ambitious players, it's fair to consider that the week-in, week-out physicality of Serie A is slightly lower than the Premier League's. Of course, that is a sweeping, general statement that doesn't apply for the whole league (take Gian Piero Gasperini's Atalanta for example), but history tells us that the physical intensity of Italian domestic football is lower.

To some, this means that their physical attributes make them stand out among the rest, and to others, the less emphasis on strength and power suits their skillsets better.

As a result, Italy has become synonymous with many former Premier League players who were written off as being 'not good enough' for the top level of English football. Yet with different styles of play and a change of scenery, many players have left the Premier League and rejuvinated, and even redefined, their careers.

Scott McTominay

Having just been named the Serie A 'Most Valuable Player' after Napoli's recent Scudetto victory, Scott McTominay's redemption arc must feel like a fever dream. From being misprofiled, misjudged and deemed unsuitable for Manchester United, Antonio Conte has honed the 28-year-old's engine, technical talent and eye for a goal to absolute perfection this season.

McTominay's signature was £25 million well spent and the Scotsman has endeared himself to Napoli fans - both with his performances and his very public appreciation of Italian culture - and looks to have set a perfect example to any player looking to 'get away' from the Premier League.

Scott McTominay has officially been immortalised in the streets of Naples...

A former religious shrine in the city centre has now been dedicated to the Scotsman 🙏💙 pic.twitter.com/RM9EvbxZkP

— Football on TNT Sports (@footballontnt) May 30, 2025

Billy Gilmour

Billy Gilmour may have started just 13 league games this season, but the 23-year-old's £12.5 million move to Naples can also be considered a resounding success. Having been drawn to Naples by Antonio Conte last summer, the Scotsman has admitted that in Italy he has "experienced things I wouldn't have back in the UK. It is an eye-opener".

As a younger Scotsman than McTominay, Gilmour's role this season has been one of nurture and development. Not particularly dissimilar to his rotation role would have been at Chelsea. Yet the lessons he can take from training in a different way, in a different country, while forming an 'inseparable' relationship with his MVP countryman, are intangible - but could serve the ex-Chelsea man brilliantly for the rest of his career.

Romelu Lukaku

Romelu Lukaku feels like the embodiment of the England-to-Italy pipeline in recent seasons. Not only has he crossed the divide multiple times - he accounts for two of the 29 permanent transfers from England to Italy since 2019 - but his moves have also underlined the nuances of finding the right league for a player’s particular skillset.

Lukaku rose to prominence at Everton before becoming a victim of Manchester United’s wasteful recruitment. Signed for £72 million in 2017, he was cast as the marquee solution to United’s attacking issues. Two seasons later, he was sold to Inter for over £60 million - as a misfit, not a failure.

At Inter, Lukaku rediscovered his identity. He fired them to second place in 2019/20, then led the line in their 2021 Scudetto win under Antonio Conte, scoring 47 league goals across two seasons. It looked like a home found - until Chelsea came calling.

Romelu Lukaku, Inter Milan pic.twitter.com/I8i2G4cutE

— The Extreme Football Enthusiast (@ExtremeFootbal4) June 5, 2025

Chelsea’s £95 million move in 2021 started promisingly before an ill-advised, discontented interview derailed his momentum. Within a year, he was back at Inter. Since returning, he’s reached a Champions League final (losing narrowly to Manchester City), won another Scudetto, and narrowly missed out on going back-to-back this year.

Lukaku hasn’t become a different player in Italy. He’s just in a league that suits him better. To the Belgian, Italy must feel like a safe haven.

In The Shadows

While ambition has been one of the key motivators behind many players making the England-Italy switch, there are also examples of Serie A providing a place for players who faced a mix of poor form and unjust media criticism to steadily rebuild their careers away from the constant scrutiny of the English media.

That's not to say that ambition was never a factor for any of the players in this category - in fact, it was likely a key factor too - but the idea of moving away from the spotlight is perceived to have taken more of a prominent role in considerations.

Kyle Walker

A potential move to Milan this summer would mark a late-career twist for Kyle Walker, The six-time Premier League winner is seemingly ready to make his loan move from Manchester to Milan a permanent one, chasing a final chapter in an already illustrious career. That is, if Milan deem him to be worth the risk.

Walker’s famous recovery pace has certainly faded slightly, and even in Serie A’s less physically demanding environment, the Englishman hasn't particularly shown he can fit in - yet. It remains to be seen whether he might prolong his career in a more tactical role. At 35 and certainly not the player he once was, his off-field influence on a young Milan side entering a soft rebuild could be immense.

There's also a more self-driven side to the move. Having spent his entire career in England, a switch abroad could prove to be more than a swansong, and potentially a welcome last-minute reinvention.

Christian Pulisic

Christian Pulisic is now two seasons into a quiet revival. Having arrived at Chelsea in 2019 as shiny £70 million prospect, the American had rusted away until moving to Milan in 2023.

He started 32 games in his debut campaign, producing 12 goals and 8 assists in a second-place finish. Despite slipping to eighth this season, Pulisic has again provided 20 goal contributions and remains well-respected amongst Milan fans.

He may never become the global superstar many once predicted, but he’s become loved by locals again - which is arguably more important.

It was a season where much did not go our way. But through all the ups and downs, @cmpulisic10 delivered night in and night out. Your Milan Club Melbourne Player of the Season: Christian Pulisic. Thank you to all our members for voting and participating #SempreMilan pic.twitter.com/ofJ9om6KFS

— Milan Club Melbourne (@milanmelbourne) May 29, 2025

Ruben Loftus-Cheek

Another once touted talent who left Chelsea for Milan, Ruben Loftus-Cheek looked like he might finally get a fair run at Milan. In his first season, he brought physicality, elegance and balance to their midfield, reigniting the potential that earned him a place in Englans's 2018 World Cup squad.

But this campaign has been cruel. He's started just 10 league games due to a series of lengthy injuries. Now 29, it feels like we may never see Loftus-Cheek at full throttle again.

Bold Movers

Within the list of players mainly comprised of those who arguably needed a change more than they may have wanted it, there are two players who stand out as having gone against the grain in their efforts to establish a legacy for themselves. In modern football, it's often typified that if a player wants to prove themselves, they will make a move into the Premier League. These players were already in positions to jump to new heights, yet still fancied the challenge of a move to Italy. Maybe it was the tomatoes after all.

Fikayo Tomori

When Fikayo Tomori left Chelsea for AC Milan, he wasn’t escaping anything - he was pursuing growth. Initially loaned out in January 2021, the £27 million move became permanent that summer. Sixteen games into his Serie A stint, Tomori was already a defensive leader in a side that finished second.

In his first full season, he helped Milan to a Scudetto. Since then, he’s remained one of Serie A’s standout defenders - quick, intelligent, aggressive. At 27, he’s become an example of how English players can thrive abroad early in their careers. The biggest mystery is why England haven’t made more of him.

Crystal Palace, Everton, Newcastle, Spurs, and West Ham are all interested in AC Milan defender Fikayo Tomori, according to @tbrfootball pic.twitter.com/L8ESX10JfG

— Football Transfers (@Transfersdotcom) June 3, 2025

Douglas Luiz

Douglas Luiz’s move from Aston Villa to Juventus in the summer of 2024 wasn’t just a bold footballing choice - it was a financial necessity. The Brazilian midfielder had grown essential to Unai Emery’s side, helping them qualify for the Champions League and producing the best form of his career at Villa Park. But with Villa facing increasing pressure from the Premier League’s Profit and Sustainability Rules, Luiz’s sale became a business decision as much as a footballing one.

Douglas Luiz. 🇧🇷 pic.twitter.com/esvr9hUspL

— Forza Juventus (@ForzaJuveEN) June 5, 2025

Despite arriving off the back of his best-ever season, Luiz made just three league starts in a campaign marred by injury and instability, and Juventus are reportedly unsure whether they want the Brazilian to be a part of their squad next season. A harsh reminder of football’s volatility.

Now 27, and still affectionately referred to as ‘Dougy Lou’ by the Villa faithful, he’ll be hoping next season brings better fortune (whether or not he is in Turin) - and that his bold switch to Serie A can eventually be remembered for more than just balancing the books.

Of course, this list hasn't covered every player who has moved from England to Italy in recent seasons. But it does offer insight into the different reasons why the transfer has become increasingly common over the past few years - which is perhaps a key reason for why Italian football is currently thriving.