The combative Belgian has attracted interest from leading sides around the world during a distinguished career at the top of the game.
He has, however, shunned the opportunity to link up with the likes of Juve in order to take on challenges that hold greater appeal to him as an individual.
Nainggolan told DAZN and Goal of his career path: "The matches against Juventus have always been special to me, because in the past they've tried to sign me but nothing ever happened.
"This is because I’d rather challenge the ‘best teams’ and try to win against them. This has always been my philosophy."
That mindset took him to Milan in the summer of 2018, with the 31-year-old determined to help Inter to get back on the trophy trail after a humbling tumble from the summit of Italian football.
Pressed on the characteristics that define him, Nainggolan added: "The desire to win, even if that sounds strange as I’ve never won anything. I’ve always wanted to win something. And that is something that has been missing for a while at Inter too.
"So winning a trophy here would mean a lot to the whole fanbase. They’ve been waiting a long time for it, as they’ve had that period where they were used to winning.
"Therefore we need to get back to being that team that is talked about worldwide, which Inter haven’t been for a bit now."
Inter’s ongoing pursuit of silverware will likely lead them back into the transfer market.
It could be that they endeavour to raid domestic rivals for Italy international midfielder Barella.
Former Cagliari man Nainggolan is a big fan of a 22-year-old following in his footsteps and admits to being able to see some of himself in Barella’s game.
He said: "Yes, especially in the way he plays, because he’s the type of player who always gives everything he has on the pitch.
"He might not make a difference with goals or assists, but he’s a vital player for a team, someone who helps the others elevate their game.
"That type of player might draw less attention to himself, but is vital to the success of the team."
Pressed on whether the pair could play in the same team, Nainggolan added: “Why not? Playing with great players is always nice.
"I joined Inter and it’s been nice to play alongside some great players.
"As all the players who were in Serie B before will tell you: 'When you start playing for a better team, everything becomes easier.' Which is true, because the team is stronger and your team-mates as well.
"I think that with Barella, it could be a great 'battle', even with both on the same side."