Adriano Galliani, former Rossoneri CEO, gave a long interview on the podcast 'Colpi da Maestro' in which he shared many anecdotes and behind-the-scenes stories from his long experience at Milan. Here are his words:
“If I had to choose just one season from my 31 years at Milan, I would say the 1993-1994 season.”
On the Milan of Sacchi, Capello, and Ancelotti:
"That Milan thought big because its president, Silvio Berlusconi, thought big. And he passed that mentality on to the club, the coaches, and the players. When we chose Sacchi, people said we were crazy. Arrigo’s teams played great football, but the year before joining Milan he hadn’t even managed to get Parma promoted from Serie B. People said Capello was Berlusconi’s favorite because Fabio hadn’t coached for years and was doing other things. The third big move was Ancelotti, who was called a ‘successful loser’ because in the two years before Milan he was at Juventus and finished second twice. It’s not only the players that should be remembered as masterstrokes, but also the coaches. After Milan I returned to Monza, and I believe a masterstroke was taking Palladino, the Primavera coach, and promoting him to the first team. Coaches have a huge impact on a team’s results."
On choosing coaches:
"There were different periods. I’ll start with Sacchi. For Berlusconi the most important thing was playing good football. The year before, we played a friendly against Parma and saw how well they played. In the Coppa Italia we drew Parma, and they came to Milan and beat us while playing very well. Berlusconi asked me whether Parma had better players than Milan. Obviously I said no. Then he asked why they played better than us. I replied: ‘Well, they must have a good coach.’ Milan advanced as runner-up in that Coppa Italia group, which Parma won. In the round of 16, who did we draw again? Parma. They came back to Milan and beat us for the second time. At that point we thought it couldn’t be a coincidence. After the return match we asked Parma’s president to go to dinner, and at that dinner we met Sacchi. We talked but didn’t conclude anything. In the following months we decided Sacchi had the right characteristics to coach Milan. When he arrived he won the league in his first year, the European Cup in his second year, and another European Cup in his third. When Sacchi joined us he didn’t ask for a salary figure, he made me name it. He said it was fine, but added that if he won, the amount would double during the year. The following season it would start from the doubled amount, and if he won the league or the European Cup again it would double again, and the same in the third year. In the end he managed to buy a few hotels in Milano Marittima (laughs)."
On the 'Condor days', Galliani had this to say:
“It comes from the film ‘Three Days of the Condor’. I thought the ‘Condor days’ were the final days of the transfer window. I’ve taken part in about a hundred transfer markets. I started my career in 1975 at Monza and finished with Monza’s 2025 transfer window. My first move was a swap: Monza took Braida and gave Peressin to Palermo. I remember every deal. Since 1975 I’ve always noticed one thing: players’ values go down as the transfer window progresses. If you want to sell a player, you should do it at the beginning of the window; if you want to buy, you should do it at the end. I think every team has more players than it actually needs. So the Condor days must be the last days. Not always, but often deals that were ‘no’ become ‘yes’, and operations that seemed impossible suddenly become possible. That’s how the Condor days were born.”
On the Condor-day deals he is most proud of, Galliani said this:
“Let’s start with the first one: Carlo Ancelotti. It was 1987. Sacchi wanted him at all costs and pushed hard to sign him despite his knee problems. Sacchi said knees can be treated, but the head cannot. It was the second-to-last day of the transfer window and the Roma president kept saying no. I had started to give up, but Braida did well to organize a dinner with Roma. That evening we realized the president kept saying no, while his son and sporting director Perinetti were saying yes. The son invited me to Rome the next day and arranged a meeting with his father. The next morning I took a plane to Rome, and what seemed impossible happened. Ancelotti helped us a lot in those seasons. But I also think that if that relationship hadn’t been created, in 2022 Carlo would have gone to Parma because he had almost signed for them."
"Another Condor deal happened in Paris in 1997 when we signed Leonardo from PSG. Capello, who had returned to Milan, absolutely wanted him, but Berlusconi and I didn’t want to spend more money and we said no. Then something incredible happened: I was in Florida and had to return to Milan the next day. While heading to the airport I saw a huge sign that said ‘Leonardo’. So I immediately called President Berlusconi and told him I’d had a vision. I flew to Paris and signed Leonardo from PSG. I was lucky to know the PSG ownership well, they received me immediately, and that’s how we got Leonardo."
Galliani added:
"Another great Condor deal was Alessandro Nesta. I was in Sardinia and every morning I had coffee with Lazio president Cragnotti. We had reached an agreement for a huge amount, 60 billion lire, but Berlusconi told me no. We had just won the Champions League qualifying rounds and would participate in the competition. That night Berlusconi was in Copenhagen with other prime ministers. I saw a TV interview where he was asked whether his ministers were free to move within the budget, and he replied that ministers could adjust the budget as they saw fit, within limits. So I seized the moment and, through one of his bodyguards, managed to speak to him. I asked: ‘As Milan’s CEO, am I like a minister?’ He said yes. I told him that if we signed Nesta we would win the Champions League, and that winning it would bring huge revenue. Berlusconi, perhaps because it was 4 a.m. and he was tired, let me understand I could sign him. My friend Fedele Confalonieri says I had the talent to immediately understand when Berlusconi said yes and meant yes, said yes but meant no, said no and meant no, or said no but meant yes. Nesta arrived and we won the Champions League, which will always stay in my heart. The joy of beating Inter in the semifinal and Juventus in the final is something that may never happen again. And Nesta helped us enormously.”
On the most complicated night:
“I’d say the one for Ibrahimović. I was in Barcelona with the Barça president and Mino Raiola. The year before, Barcelona had bought Ibra from Inter for a huge fee. I thought it was impossible to sign him after just one year. A few days before the transfer window closed, Raiola, who was the master of the market, called me and told me to come to Barcelona because it could be done. I went there and started a big battle to sign him, and in the end I managed to get him on loan with an option to buy. I had to convince Ibra, so I went to his house where his wife and children were also there. His wife left in the morning and came back early afternoon and found me still there. She hadn’t asked who I was before. Ibra told her and added that until he signed for Milan, I wouldn’t leave their house. Zlatan eventually signed and that year we won the league.”
On Džeko, Galliani said:
“Braida and I were hiding in Sarajevo, which still showed the scars of war. We were very close to signing Džeko, who had photos of Gullit and Van Basten in his room.”
On his masterstroke:
"The masterstroke I share with Braida was Marco van Basten. It may not have been the most difficult deal, but I believe Marco was the best of them all."
