His time at Villa has been a mix of dazzling moments and frustrating setbacks. While Bailey has produced flashes of brilliance in the Premier League, injuries and inconsistent form have often prevented him from cementing a regular starting role under successive managers.
Roma’s interest in Bailey comes as part of an ambitious summer rebuild. Should the deal go through, he would become their seventh signing of the window and their second arrival from the Premier League, following the loan capture of Brighton striker Evan Ferguson.
The race for his signature, however, is far from straightforward. Besiktas and several Saudi clubs are also in the hunt, offering lucrative packages, but Roma’s sporting project and the opportunity to shine in Serie A remain highly appealing to the player.
Another key factor could be the influence of manager Gian Piero Gasperini, who has made no secret of his desire to add more attacking firepower to bolster Roma’s domestic and European ambitions. With Bailey’s blend of pace, creativity, and experience, he could well be the kind of player to give Roma that extra edge in the final third.