MightyTips exclusive: Andrea Pirlo, AC Milan great, reflects on his nicknames, star partners, and the Miracle of Istanbul

Former AC Milan and Italy star Andrea Pirlo shared memories from his legendary career with MightyTips exclusively, while appearing at the Golden Boomerang Awards 2025 gala hosted by the Boomerang Partners.

Boomerang Partners, a long-term MightyTips partner and a globally growing iGaming brand, gathered over 400 partner teams from around the world on May 20, 2025, to celebrate the winners of the second annual partners' competition. The grand event at the iconic San Siro stadium was made possible thanks to the partnership between Boomerang Partners and AC Milan, one of the world's premier football clubs.

A standout guest at the Golden Boomerang Awards 2025 was AC Milan legend Andrea Pirlo. He congratulated the winners and presented the awards while also participating in a charity auction, with all proceeds generously donated to Fondazione Milan.

Andrea sat with MightyTips to answer several questions about his illustrious career.

MightyTips: You had many nicknames – Architect, Professor, Maestro, Mozart, Metronome. Which one did you like the most? Was there one you particularly disliked?

Andrea Pirlo: To be honest, I don't particularly like any of them. If I had to choose, Maestro is the one I dislike the least, simply because it was so widely used that it became somewhat familiar. But in general, I prefer to be known simply as Andrea.

Gattuso: "Pirlo has the face of an angel but he is a son of a b***h. One day, I was eating at the training ground and forgot my phone on the table. Pirlo took it and sent this to the AC Milan president: 'Dear President, if you give me the salary I want, you can have my sister!' pic.twitter.com/5Bhx98Kg2t

— SPORTbible (@sportbible) April 28, 2022

MightyTips: Gennaro Gattuso once recalled: "The first time I played with Pirlo, I asked myself if I should change profession." Was there ever a moment when you doubted your professional choice?

Andrea Pirlo: I've never doubted my path. From a very young age, I knew that football would be my life. I was always sure that I would become a professional player. My conviction in my abilities and potential never wavered, and I never considered any other profession.

MightyTips: Of all your club and Italy teammates, who you admired the most as football players?

Andrea Pirlo: I admired many teammates, but if I had to choose, I'd say Paolo Maldini for his leadership and consistency, Alessandro Nesta and Alessandro Costacurta for their exceptional defensive skills, and Francesco Totti for his creativity. Additionally, Alessandro Del Piero and Gianluigi Buffon were remarkable for their skill and influence on the team. So, I believe I have played with the top footballers of my time.

MightyTips: They say, "what doesn't kill you makes you stronger." Which defeat impacted you the most as a person and as a player?

Andrea Pirlo: The defeat that affected me the most was the 2005 [UEFA] Champions League final in Istanbul. It was a game that we played almost perfectly, and yet it ended in a way that is still difficult to comprehend. The pain of that loss was profound, not just because of the result, but because we were so close to achieving something extraordinary.

MightyTips: Still, you've won it all — from the UEFA Champions League to the FIFA World Cup. What stands out most to you personally?

Andrea Pirlo: Every child who wants to be a footballer also dreams of winning the World Cup. It's the ultimate prize, the pinnacle of success in our sport. For me, having the opportunity to lift this trophy is the realization of a dream that seems almost unattainable for so many. It's a moment that transcends football.

MightyTips: You defined the deep-lying playmaker role. Do any current players remind you of yourself?

Andrea Pirlo: Yes, there are a few players who come to mind. Frenkie de Jong from Barcelona possesses a similar ability to control the game from deep thanks to his precise passing and vision. Hakan Çalhanoğlu at Inter also impresses with his technical skills and understanding of the game. In a different way, but still notable, is Nicolò Rovella from Lazio, who shows great game intelligence.