The defender turned down the chance to join Arsene Wenger’s side as a teenager
The centre-back was at Livorno in the third tier of Italian football when he caught the attention of the Gunners.
But Chiellini, who is now 36, didn’t want to let down his childhood club and opted to remain in Italy.
“In hindsight, I was a fool to decline that offer,” he told So Foot (via Goal).
“I was 16, I played in Serie C, I got a huge offer.
“I didn’t feel ready. If I had accepted, it would have given the impression of betraying Livorno.”
Chiellini eventually joined Fiorentina in 2004 and moved to Juventus a year later, where he has been ever since.
The 105-time Italy international has won nine Serie A titles in Turin, but the Old Lady face a stern challenge to their domestic dominance this season from Zlatan Ibrahimovic’s AC Milan.
“I respect Zlatan a lot, we respect each other,” Chiellini said.
“We were team-mates, in my first season at Juve. I was never afraid to face him, never took a step back in front of him. He already had extraordinary physical strength.
“After that he became the absolute enemy when he moved. The best enemy of my career is Ibrahimovic, without a doubt.”