You started your career at your boyhood club AC Milan in the youth set up before going to play for the first team for fourteen seasons. What are your early memories of life at the club as a youngster?
“I have only fantastic memories because I grew up as an AC Milan fan and it was an honour for me to be able to represent the club.
“I came through the system at a time when the club was struggling in Serie A prior to the takeover of Silvio Berlusconi.
“Those times were tough and I had to learn quickly in such a tough environment.
“However, once Berlusconi took charge of the club, everything changed for the better and we became a phenomenal club in Italian football and also in European and continental competition.
”We won so many trophies during my time at the club as a professional and looking back, it was a golden age for AC Milan and our supporters.”
You played under an iconic manager in world football in Arrigo Sacchi who led the club to a Scudetto and two European Cups during his time in charge. What was Sacchi like to work with on a daily basis from a player’s perspective?
“Prior to working with Arrigo Sacchi, I worked under Ilario Castagner and Nils Liedholm at AC Milan while I was a youth player at the club.
“I learned from both of those coaches but as a team, we did not win major honours under them.
“Liedholm won the Scudetto during his first spell in charge of the club prior in the late 1970s but could not repeat it when I played under him.
“Then, Arrigo Sacchi arrived from Serie B side Parma to become our new manager in 1987 and things changed dramatically.
“He was a visionary who changed the way that people thought about football in Italy. His style was the opposite of Catenaccio.
“We played free-flowing attacking football with intensity under him and had great success with it too by winning a Scudetto and two European Cups under him back to back.
“Overall, Sacchi had such an impact on AC Milan as a club and football as a whole that when I talk about football, I talk about it in terms of football pre-Sacchi and football post-Sacchi.
“He changed the game in so many ways in terms of his style of play with the teams that he managed and the success that he achieved doing so.
“Winning was important to him but you had to win in style. That was of paramount importance to him and how he went about his work.”
His training sessions were known for their high levels of intensity. How did you find those?
“Tough (laughs). Every day was demanding because he was such a workaholic who wanted you to give every ounce of energy that you had for the development of you and the team.
“We regularly had double training sessions under him and even triple training sessions from time to time.
”That was unusual at the time but he was ahead of the curve as our success showcased.”
You won the first of two European cups under him by defeating Steaua București by four goals to nil in the 1989 European Cup final in Camp Nou. What are your memories of that game?
“It was a fantastic memory for me because we played at Camp Nou in Barcelona which is such an iconic stadium.
“Added to that, the majority of the crowd in the stadium on the night of the final were Milan fans. They supported us incredibly well and drove us on to victory.
“The game itself was a night were our football shone. Two goals each from Marco Van Basten and Ruud Gullit helped us on our way to win the first of two European Cups under Arrigo.
At Milan, you retained the European Cup under Sacchi by defeating Benfica in the 1990 final by one goal to nil in Vienna. How did that game differ from the final the year before in Barcelona?
“That game was much tougher than the year before against Steaua as the scoreline shows.
“Benfica are one of Europe’s great clubs and they had a top side when we faced them in the final of 1990.
”Benfica put up a tough fight and stopped us from scoring for over an hour before Frank Rijkaard scored a fantastic goal to win the game for us.
”It was an incredible feeling to win the European Cup in back-to-back years and a period of success that defined our team and Sacchi as our coach.”
That team under Sacchi is referred to as ‘The Immortals’. How does it feel to be part of such a highly revered team in football history?
“It feels amazing for me to be able to say that I was a part of that team because I am proud of all that we achieved together.
“We worked hard under a revolutionary coach who was ahead of the curve and we deserved the success that came our way as a result of that.
“We also played entertaining and purposeful football which was enjoyed by fans across Europe.
“We showed everyone that Italian teams can play beautiful football and not just focus on clean sheets and defending leads. That was also pleasing for me and my teammates.”
Post Sacchi, you stayed at Milan and enjoyed another period of success under Fabio Capello. You won a third European Cup under him against Barcelona in 1994 in Athens. Can you sum up what that experience was like under Capello?
“Fabio Capello was a former footballer of Milan and he knew better than others how to handle the pressure of managing Milan and how to continue our success.
”He took over the team in the summer of 1991 and regenerated our team at the right time as results and performances had just started to dip from their previous levels in the last season of Arrigo Sacchi.
“He brought new energy to the club and led us to more success at home and abroad.
“We won four Scudettos and the European Cup in 1994 with an entertaining style under him too.
“In terms of the 1994 European Cup final in Athens against Barcelona, that was the most pleasing of the three finals that I won at Milan because I played the full game.
“In the wins of 1989 and 1990, I started on the bench and came on during both games to serve a purpose for the team and help see out our victories whereas in 1994, I was at the heart of the victory in a greater sense.
“We played against the Barcelona of Johan Cruyff with players such as Romario and Hristo Stoichkov in their team yet we managed to defeat them by four goals to nil.
“We played one of our best ever games under Capello that night by dominating the game and destroying Barcelona – in sporting terms – on the night.
“That was one of the best nights of my life and in my football career.
“To win three European Cups is the stuff of dreams and to have done so under two great managers in Sacchi and Capello was extra special for me.”
You left Milan in 1996 after fourteen years at the club as a first-team player. You played at other Italian clubs such as Reggiana and Brescia before joining Watford in 2001 under Gianluca Vialli. What are your memories of your time in English football?
“I will always be thankful to Luca Vialli who made a dream of mine come true which was to play in English football.
”I love the passion of the fans in England and I wanted to experience it for myself.
“Even though I was 38 when I joined Watford, I loved my time there.
“Working under Luca was amazing because he was such a great man and a top gaffer as you say in the UK (laughs).
“It was not the best season at Watford as we missed out on the Championship playoffs but I am still thankful to Luca for the opportunity to play in England and to the Watford fans for their support during my time there.”
Upon retirement, you returned to work at AC Milan under your former teammate Carlo Ancelotti who was then manager of the club. What was it like to work alongside someone like Carlo?
“Working with Carlo was fantastic. I had worked with the youth teams for four seasons before Carlo promoted me to work alongside him and Mauro Tassotti.”
“I loved working with the first team because I learned so much from Carlo and from the elite players that we had at the club during that period of time.”
Last but not least, Filippo, who would you rank as the best footballers that you played alongside during your playing career at AC Milan?
“That is a very tough question. However, if I had to create a podium that only three players could stand on them I would select Franco Baresi at number one, Marco Van Basten at number two and Paolo Maldini at number three.
“I played alongside many more great players who it was tough to leave out but those would be my top three.
”All three of those guys were world-class footballers who achieved so much in the game yet worked so hard every day as if it was their first day in football.
”They were a joy to play alongside as were all of my other teammates.”