According to The Athletic’s David Ornstein, the two clubs are discussing a deal that would see Bailey, 28, join Roma on an initial loan with an obligation to buy.
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Bailey is currently training separately from the rest of the squad as they prepare for the upcoming 2025-26 campaign.
The winger is understood to be one of several Villa players that have been deemed surplus to requirements by Unai Emery, alongside Alex Moreno and Leander Dendoncker.
Turkish side Besiktas, and several Saudi Pro League clubs are said to be interested in Bailey, but Roma are the strongest suitors currently.