The club is bracing itself for the departure of Christian Pulisic next summer and are looking at the former Bayer Leverkusen man to replace him.
Pulisic will have a year left on his contract when summer comes around, and he wants regular playing time.
Chelsea are weighing up a move for Bailey, a close friend of Raheem Sterling. The London club has had an eye on him since he emerged at Genk years ago.
The Blues seriously considered signing Bailey in January 2017 before he joined Leverkusen. They scouted him extensively and pondered a move. Chelsea had been keeping a keen eye on the Belgian market after bringing in Romelu Lukaku and Kevin De Bruyne from there.
There were persistent rumours about Chelsea scouting and monitoring the then-youngster to replace Willian and Pedro Rodriguez. However, the German club took the risk, signing him for €20 million.
After struggling to adapt in his first half-season at the club, Bailey exploded in his first complete campaign.
In the 2017/18 season, he scored 12 goals and assisted six more in 34 appearances for Die Werkself. He followed it with two disappointing seasons before a brilliant 2020/21 campaign.
Bailey scored 15 goals and 11 assists in 40 games, prompting Villa to sign him for £30 million. But injuries derailed his debut Premier League campaign as he made only 18 appearances and scored one goal.
The 25-year-old is back to his best this season, netting four goals and two assists in 16 games.
Chelsea have missed a 1v1 specialist with an end product like Bailey in their team. It is no surprise to see them chasing him.
Bailey can operate seamlessly on the left and right flank. He makes dangerous runs on and off the ball.
He recently reaffirmed his desire to continue with Villa, claiming that his chapter was only starting. However, Chelsea’s interest could turn his head.
The allure of Champions League football is irresistible, and it would also help that he would be playing in attack with a close friend.
There are also rumours he is a closet Chelsea fan after being pictured in the club’s jersey.
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