The Jamaica international is in talks with Roma over a move to Italy.
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And Bailey's agent, Craig Butler, has hinted a move is in the works after comments on social media over the weekend.
He posted: "Rome, such a powerful city, such a beautiful city, rich in culture and history.
"A city that rewards courage and honor: conquer the crowd like a gladiator, and you will win your freedom. A cryptic message sent many years ago that still holds true today."
Bailey is on track to sign for Roma this week, with his contract at Villa running to 2027.