On Tuesday, May 20, Boomerang Partners, a globally growing brand, hosted the Golden Boomerang Awards 2025 ceremony in Milan at the famous San Siro stadium
This was possible thanks to the brand’s strategic partnership with iconic AC Milan. The football club’s Legend, Andrea Pirlo, was one of the main guests and participants of the grand event. He presented awards in 11 categories and gave an interview in which he touched on the glorious moments of his career and life. As he is known in the football world, Il Maestro shared memories of his career beginning, the brightest victories, and allowed a glimpse into his life outside of football.
The early days of Andrea Pirlo
Andrea Pirlo’s journey in football began in his hometown of Flero. It is a small town in Brescia province. From a young age, it was clear that he possessed a unique talent and vision for the game. Pirlo started his professional career in 1995 with Brescia, where he quickly caught the attention of larger clubs due to his exceptional passing ability and strategic thinking on the field. His early years were marked by a dedication to honing his skills and a deep understanding of the game that would later define his career.
“At that time, it was just having fun but keeping in mind only one target: to do my best to become a footballer, I didn’t imagine getting another type of work. Furthermore, I was sure I would become a professional football player sooner or later,” Pirlo recalls.“Fortunately, I had the pleasure to meet different coaches during various periods in my life, all of whom gave me a lot, both from a professional and personal point of view.”
Glory and trophies
Pirlo’s move to AC Milan in 2001 marked the beginning of a golden era for both the player and the club. He became a key figure in the team’s midfield, renowned for his precise passing and ability to control the game. Andrea played a crucial role in helping AC Milan win numerous domestic and international titles, including two UEFA Champions League trophies (2003 and 2007) and Serie A titles (2004 and 2011). At the same time (2006), he became a world champion with the Italian national team.
“Something can happen from time to time in your life with a negative perspective, then it comes back again after years and completely changes the direction of things. Like it happened with AC Milan, when we lost the Final of the Champions League against Liverpool, and two years later we rematched and won. This happened just in time, because time only can give you such a feeling”, says Pirlo.
Memorable teammates
Throughout his career, Pirlo played alongside some of the greatest footballers of his generation. From Paolo Maldini and Dida to Alessandro Nesta and Gennaro Gattuso, the Maestro’s teammates were instrumental in his success. Asked who is the strongest player he has ever played with, Andrea named Brazilian striker Ronaldo.
“He mostly impressed me with his toughness and technical skills. I believe he has been the player who has changed the way of playing football of my generation because he has been the first one to combine technical issues with the speed during that period of time in football”, Pirlo recalls.
Andrea also shared his experience of playing alongside his childhood idol, Roberto Baggio: “I was thrilled to play alongside him first at Inter and then at Brescia. It was great having him alongside during the training and the games, and endeavoring to adopt some of his secrets. So, this was another dream of mine that came true”.
The Art of Winning
The Golden Boomerang Awards 2025 slogan, “The Art of Winning,” perfectly encapsulates Pirlo’s approach to football. Known for his ability to read the game, Andrea believes that winning is about physical prowess, mental strength, and strategic thinking. The player’s vision and precision on the field were instrumental in his team’s success. One of the brightest episodes of the footballer’s career was his Panenka penalty at Euro 2012, which became a legendary symbol of calmness.
“It wasn’t my purpose to play on the nerves of my opponent or something, but I thought it was the most appropriate solution to score a goal. I used to always find the easiest ways to create a positive boost for my team, so at that very moment, I was just thinking about it as the best choice,” says Pirlo. “Eventually, we play and we live to achieve our goals. It means to win every challenge you face. This tagline (“The Art of Winning”) is the same as Boomerang shares, so I totally agree with them.”
Life beyond football
Off the field, Pirlo is a family man who values his privacy. He has spoken about the importance of balancing his personal and professional life. Pirlo’s love for wine and his vineyard in Italy are well-known, providing him with a passion outside of football. He admitted that if he were creating a wine called ‘The Art of Winning’, he would choose a wine with grand structure. The Maestro also talked about giving his PlayStation to his children. He often played the console with his teammates when he was a player, and it was one of his favorite leisure activities.
Andrea also recalled the daunting challenges players aiming for a successful career must face. They spend much time travelling, staying in hotels more often than at home. Such sacrifices they make to achieve their goals. Not everyone succeeds, but Pirlo did and became one of the greatest players in history.
“A plenty of times I was with my team right on my birthday because my day falls on the terms of playing season, so it happened to me to celebrate without my family but with my teammates many times”, recalled Pirlo. “There were more characteristic parties when I turned 20, 30, and 40, and we had fun. Other birthdays were quite ordinary”.
The evolution of football
Football has undergone major changes in the last 15-20 years. It has become faster and more athletic. Teams have to play more matches per season than ever before. This requires sacrifice, discipline and fitness from the players. These requirements have always been crucial for the No. 1 sport, but now they take on a special significance. That said, there is an important difference between the two generations – those who played during Pirlo’s time and those who are conquering the football world now.
“These are two different generations, and they are quite difficult to compare. Football was everything for us, we had other demands and we were focused on football only, meanwhile, today they have more entertainment issues, more things to think of… Social media influence it’s complicated. The world has totally changed. And it’s difficult to put together those two things,” believes Pirlo.
The decision to retire
Pirlo’s decision to retire was not an easy one. After a long and successful career, he felt it was time to step away from the game he loved. The decision was driven by a desire to spend more time with his family and pursue other interests. Pirlo has since transitioned into a new phase of his life, focusing on his vineyard and other business ventures. At the same time, he is also trying his hand at a coaching career. From 2020 to 2021, he coached Juventus (first the youth team, then the main team), from 2022 to 2023, he managed Fatih Karagümrük SK in Turkey, and from 2023 to 2024, he returned to Italy, to Sampdoria. On August 29, 2024, Andrea left the club.
“When some physical challenges come into your life, you wake up in the morning realizing that you don’t feel the same enthusiasm to go on training anymore, I believe this is the right moment to start thinking about ending the career,” Pirlo admits. “I was lucky enough to feel the moment when to quit from this or that team or to stop my career.”
Epilogue
The rain that accompanied Andrea Pirlo’s interview did not affect his stamina. As he admitted when answering one of the questions, he would always choose the latter between wind and rain as a footballer. It is easier to adapt to it. There are similarities between the affiliate marketing industry and football. The ability to adjust allows you to achieve big goals. The Golden Boomerang Awards 2025 allowed us to see this. The top 11 teams of the tournament stood up to some serious competition in the industry and received their awards from Andrea’s hands. By the way, Boomerang Partners is already working on the third season of the competition, which has become a trendsetter in the industry.