The Italy international spoke about how close he was to signing for some of Europe's leading clubs and tipped Clarence Seedorf to be a success at Milan - if he is offered the job
The 33-year-old ended a 10-year spell with Milan in 2011 and, prior to signing for Juventus, a decision he believes was the best of his career, Pirlo says he was not short of suitors keen to secure his services.
"I had already reached an agreement with Chelsea, then after Berlusconi intervened and I stayed at Milan. I was also very close with Capello at Real Madrid and nearly joined them in 2006," he explained in his autobiography.
"Guardiola then convinced me to join Barcelona in 2011, but Berlusconi stepped in again."
The former Milan playmaker added he was happy with the decision to sign for Juventus, but stressed his departure from the Rossoneri was born out of a desire to seek a new challenge.
"Surely it was the best decision of my career to sign for Juventus," he said. "Do I regret leaving Milan? I decided I needed a change. I needed to find new ideas and that was the best thing for both parties."
Clarence Seedorf has been touted as a potential successor to Massimiliano Allegri at Milan and Pirlo believes his former team-mate is well-equipped to take the reins at San Siro.
"He is a great character, he has charisma and could do very well at Milan. But now he's still playing in Brazil, we will see when it stops," he added.
It is a career path Pirlo also harbours aspirations to follow and he credited current coach Antonio Conte for inspiring him to one day swap life on the pitch for life in the dugout.
He said: "Thanks to Conte I got the urge of coaching and I thank him for that. We will see what happens in the future."
Pirlo could pick up his second successive league winners medal with Juventus as early as this weekend.