ALTHOUGH Leon Bailey’s English Premier League journey seems to be coming to an end, the Reggae Boyz winger is set to make history as the second-ever Jamaican born player to play in Italy’s top flight with AS Roma.

The Jamaica Observer has learnt that the 28-year-old winger, who missed Aston Villa’s goalless draw with Newcastle United on Saturday, is to undergo a medical assessment in Rome on Monday, ahead of a season-long loan from Aston Villa.

It is said that Bailey, who has agreed personal terms with the Italian club, could be officially unveiled on Tuesday. He would join Trivante Stewart (Salernitana FC) as the only Jamaican-born footballers to play in the Serie A.

His agent Craig Butler landed in the Italian capital over the weekend to finalise the deal, with Roma expected to pay a three-million-pound loan fee ($650.9 million) with an option to make the move permanent for 17 million pounds ($3.6 billion). Butler couldn’t be reached for comment by the Observer but on social media he hinted that the move was imminent.

“We believe, we work and we deliver,” Butler wrote. “Rome [is] such a powerful and beautiful city, rich in culture and history. A city that rewards bravery [and] honour.”

Bailey, who has made 144 appearances for Villa since joining in 2021 for 30 million pounds ($6.5 billion), was willing to make the move away from England after not receiving assurances of game time by Villa Manager Unai Emery.

Bailey joined Villa’s preseason at the end of July after receiving a break following Jamaica’s Concacaf Gold Cup campaign during which they were knocked out in the first round. He started in several games, including a 4-0 win against Roma on August 6 when the initial interest reportedly began.

On Friday, during the club’s press conference ahead of their clash with Newcastle, Emery revealed that the Jamaican was on the verge of exiting the club.

“He’s unavailable because he’s in contact with another club,” Emery said. “There’s a possibility he might leave. We’ll accept his eventual decision to leave.”

The Observer understands that Bailey’s preference was to stay in England but a move to his preferred clubs never materialised. In fact, the former Bayer Leverkusen and Genk star was on Manchester United’s shortlist of attackers during the winter transfer window, as previously reported by the Athletic, but the club has since moved on to Matheus Cunha, Bryan Mbuemo and Benjamin Sesko.

Several Spanish clubs tried to persuade Bailey to join them this summer but he preferred the Roma project under Gasperini, who had success with Atalanta over his nine years. Though not confirming the move, Gasperini on Saturday said additions like Bailey are necessary for the club to compete.

“We’ve not had anyone new come in for three weeks now. If possible, we should get some new players without losing any,” he said. “I have been very clear with the club about what needs to be done. Now, we just hope that we can do it.”

Italian Gasperini, who won the Europa League and led Atalanta to multiple Champions League qualifications during his nine-year stint, has been credited for the success of many top attackers, including Ademola Lookman, Duvan Zapata, Luis Muriel and Rasmus Hojlund who earned a mega move to Manchester United in 2023. It’s believed he could help Bailey return to the level he showed two seasons ago.

Following a standout 2023/24 season in which he notched 14 goals and 14 assists across all competitions, his production dipped last season to just two goals and four assists while slipping down the pecking order — and recent signings of forwards Donyell Malen and Evann Guessand also signalled Emery’s intent regarding Bailey’s future.

Roma are hoping to register Bailey ahead of Saturday’s league opener against Bologna. He will also be playing European football for the third-consecutive season, with the club competing in this season’s UEFA Europa League.

In this March 4, 2025 photo Leon Bailey (left) celebrates with Aston Villa teammates Marcus Rashford (centre) and Tyrone Mings after scoring the club’s opening goal during the 3-1 Champions League round-of-16, first-leg win over Club Brugge at Jan Breydel Stadium in Belgium.

Jamaica’s Leon Bailey (left) takes on Guatemala’s Carlos Aguilar during the Concacaf World Cup Qualifier at the National Stadium on Tuesday, June 10, 2025. (Photo: Joseph Wellington)

BUTLER… Rome [is] such a powerful and beautiful city, rich in culture and history (Photo: Observer file)

Aston Villa’s Leon Bailey (right) takes on Arsenal’s Declan Rice (centre) as Oleksandr Zinchenko looks on during the English Premier League football match at Emirates Stadium in London on April 14, 2024. (Photo: AFP)