Three Brazilians and four Dutchmen: The best AC Milan XI from Silvio Berlusconi’s era

By Oliver Fisher -

The passing of Silvio Berlusconi was announced earlier today and it has prompted a lot of reflections regarding his illustrious and successful 31-year tenure as AC Milan owner.

Berlusconi dabbled in the media industry and politics, but his name will forever be synonymous with what he did as the owner and president of Milan, his boyhood club that he bought and saved from bankruptcy in the 1980s.

He was the main man of the Rossoneri from 1986 until 2017 during which time the club won 29 trophies, going from being a debt-ridden laughing stock to a European superpower.

Those trophies included five Champions Leagues, eight Scudetto, seven Supercoppa Italiani, five European Super Cup, two Intercontinental Cups, one FIFA Club World Cup and one Coppa Italia.

Along with the trophies came so many amazing memories, goals and of course players that graced the pitch, including record-breakers and several Ballon d’Or winners.

We decided to take on the difficult task of naming the best XI of players from Berlusconi’s era.

GK: Dida

Dida arrived at Milan in 2000 and was the starter for near enough a decade, winning a Scudetto and two Champions Leagues, with the first of those coming after he saved three penalties in the 2003 final against rivals Juventus.

The Brazilian is one of four Milan keepers with 300 career appearances and he just about beats Sebastiano Rossi to be our starting goalkeeper.

RB: Cafu

Another Brazilian makes it into the line-up and this time it is Cafu, who went down as one of the first modern full-backs and someone who changed the role thanks to his attacking prowess and the ground he covered.

At Milan he won a Scudetto, the Supercoppa, one Champions League, two UEFA Super Cups and the FIFA Club World Cup, having made the move north from Roma in 2003.

CB: Alessandro Nesta

Nesta, like Cafu, made a move north from the capital in the early 2000s, but from Lazio. He is without a doubt considered one of the best defenders of all time thanks to his timing, anticipation, judgement, tackling and his distribution too.

He cost €30m but was a player Berlusconi strongly wanted. The fact he won 10 trophies in his 10-year spell – including two Scudetti and two Champions Leagues – suggests it was the right move.

CB: Franco Baresi

Not a Berlusconi signing, but Baresi is someone who became synonymous with his era. There are not enough superlatives to describe a man who spent his entire 20-year career with the Rossoneri, captaining them for 15 seasons.

At Milan hee won three UEFA Champions League titles, six Serie A titles, four Supercoppa Italiana titles, two European Super Cups and two Intercontinental Cups, becoming quite simply an icon and even having his number be retired.

LB: Paolo Maldini

Maldini made his debut as a bright-eyed teenager two years before Berlusconi bought the club, and like Baresi he spent his entire playing career with his beloved Milan, which was 25 seasons plus the captain’s arm band from 1997 onwards.

Quite simply one of the greatest defenders ever, Maldini won 26 trophies with Milan including the European Cup/UEFA Champions League five times, seven Serie A titles, one Coppa Italia, five Supercoppa Italiana titles, five UEFA Super Cups, two Intercontinental Cups and one FIFA Club World Cup.

CM: Clarence Seedorf

Seedorf’s career ran parallel to Nesta’s as he joined in 2002 and left in 2012, and he is considered to be one of the best midfielders of his generation and was given credit for modernising the role.

He remains the only player to win the Champions League with three clubs, winning nine trophies during his time at Milan, and Berlusconi even brought him back for a spell as the head coach in 2013-14.

CM: Frank Rijkaard

Rijkaard is the second of three Dutch midfielders present and former part of the ‘Tre Tulipani’ (Three Tulips) along with Ruud Gullit and Marco van Basten. He joined from Sporting CP in 1988 and went on to make 201 appearances for the club, with 26 goals and 25 assists.

The Dutchman scored the winning goal in the 1990 European Cup final against Benfica, which would be one of nine trophies he won at the club, including two Scudetto and two European Cups.

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CM: Ruud Gullit

Gullit arrived a year prior to Rijkaard, joining Milan from PSV for what was then a world record transfer fee, winning the Ballon d’Or too in 1987.

He would go on to win three Serie A titles and two European Cups with Milan, amassing 171 appearances with 56 goals and 40 assists, numbers that wouldn’t be bad for a striker despite the fact he played a multitude of roles.

CAM: Kaka

Another player who needs little introduction, Kaká is widely considered one of the best players of the 2000s, having joined Milan from Sao Paolo in 2003 for an €8.5m fee that Berlusconi would go on to describe as ‘peanuts’.

The Brazilian helped Milan win the Serie A title in his first season and then he was the top scorer in the 2006–07 UEFA Champions League campaign which saw the Diavolo hoist the trophy. He wont the 2007 Ballon d’Or and ended his time at Milan with 104 goals and 81 assists in 307 games, plus five trophies.

ST: Andriy Shevchenko

Shevchenko arrived from Dynamo Kyiv for a fee of around €25m after a glowing scouting report arrived back at Milan’s headquarters. He racked up 175 goals for the Rossoneri, making him the second top scorer in the club’s history.

He also leads the Derby della Madonnina in scoring with 14 goals and he won five trophies with Milan in his seven-year first spell, with his most prestigious moment perhaps being the Ballon d’Or in 2004.

ST: Marco van Basten

Many icons of football came and went during Berlusconi’s time as Milan owner but he rarely expressed much favouritism. That lasted until an interview with Corriere dello Sport in 2020, when he named Van Basten as his favourite player.

The Dutchman scored 125 goals and added 49 assists in 201 games for Milan, who he joined from Ajax. Van Basten won the Ballon d’Or three times – in 1988, 1989 and 1992 – and he won 10 trophies with the Rossoneri.

Bench: Rossi, Tassotti, Thiago Silva, Pirlo, Gattuso, Ibrahimovic, Weah.

Tags AC Milan Silvio Berlusconi


  1. “Calamity” Dida? 😬. I’ll never understand why he’s held in such high regard. The guy was a complete joke – especially after the flare incident.

      1. Mass hysteria over a comment as usual… Did any of you actually watch the pens against Juve in 2003 (that everyone always brings up when hyping Dida)? No other keeper in the world could’ve saved those Juve bowling balls I guess. And don’t get me started on 2005 final against Liverpool in which he was responsible for two of their goals. I’d have gotten rid of him after that but they didn’t for some inexplicable reason and lo and behold he only got worse.

    1. Are you crazy!? Some seasons he was a bit up and down, but he was extremely good for 2-3 seasons, better than Maignan. His agility and reach was incredible. Far better than Seba Rossi.

      For me there is also a close call between Desailly and Seedorf. The former was far better defensively – a complete rock of a defensive midfielder.

      1. Dida wasn’t a joke, he was just erratic at times. Also the first (I think) United goal at old Trafford in 2007 he always flapping like a seal…Leeds United, and I also think he could have done a lot better on Smicer’s goal in 2005…that said he was a great shot stopper. His 2003 pen shoot out performance made him a legend.

        I always felt that Dida was great reacting, if he has time to think he could often falter.

        If he stays long enough, I think Mike will surpass both Rossi and Dida.

      2. Well, I guess the man sitting in front of the defence would be Frank Rijkaard and not Seedorf. So, the competition would be between Rijkaard and Desailly. This also explains why Pirlo is on the bench.

        All in all, the array of stars that Berlusconi brought to Milan was legendary. Gullit could easily be the #10, but he drops further into the midfield for Kaka.

    2. i wouldnt call him a complete joke but he certainly regressed later on and personally id pick sebastiano rossi instead but as dida won worlds best keeper award i guess he makes the most sense, but not my choice either,

      1. He was literally great, people keeping stats always ranked him high. Not sure what are you talking about, he was bad last season…

        1. i didnt say in his last season as i said “but he certainly regressed later on” whichj i stand by as he started making more blunders and eventually was replaced.

          Rossi has always been my favourite ac milan goal keeper so my view might be a bit color blind but as i also said that dida propably makes the most logical choice nevertheless and i defently didnt bash dida to any extent by what i said.

    3. Milan had a world class team but Dida was “a joke”, they didn’t bother getting a better goalkeeper. Sure. Dejan, you are so clueless, like always. 😀

      1. In terms of consistency, Abbiati was the best. But he had to move to the bench as Dida was crazily good for few seasons. Seba Rossi was a good one, but in terms of ability I would rate Abbiati above him.

    4. Dida was solid but started to get old and inconsistent. When he was younger he was one of the best penalty blocking keepers in Football.

    5. He wasn’t a complete joke. He was a fantastic goalkeeper. He was injured by the flare and it effected his performances.

  2. Generally speaking agree with the XI and bench. Honorable mention for Desailly, Rui Costa, Boban, Savicevic, Albertini …. and maybe even SuperPippo for his 2007 final performance.

    A plethora of stars that stand in stark contrast to the banter era, its almost embarrassing some of the players that followed the incredible legacy of Berlusconi’s finest.

      1. @Malda

        Yeah fair enough, on reflection what he lacked in general play he more than made up with many important goals. Plus he played for a decade in a very successful period for the Rossoneri

        No need for the “maybe” , I agree

  3. I might even swap Pirlo for Seedorf in the starting lineup. Honestly, the bench should be expanded to the modern 12, which would then be the ones in the article: Rossi, Tassotti, Thiago Silva, Pirlo, Gattuso, Ibrahimovic, Weah; PLUS: Boban, Savicevic, Albertini, Inzaghi, Costacurta. Honorable mentions then to Rui Costa, Simone, Abbiati, Bierhoff (almost singlehandedly won the 1999 scudetto), Donadoni.

    1. Yes, what a bench! I would say Jaap Stam also, but I can’t withdraw anyone from your suggestions and he only played two seasons with Milan, so I totally agree with you.

      1. I think that Maldini-Stam-Nesta-Cafu defense was better than Maldini-Baresi-Galli-Tassotti. Actually that whole 2004-2006 squad might have been better than the 1988-1992ish crew. Some individuals from the earlier one might have been better than anyone in the latter, but overall I think the 2004-2006 was more stacked. Kind of crazy to think about actually, and as much as I love Carletto it confirms he is more of a cup coach. We should have won more scudettos during the 2000s.

        1. You’re out to lunch. The 1988-1992 team would have slaughtered the 2004-2006 squad and every other team since and probably before! There is no comparison between Van Basten and Gullit and Shevchenko and Kaka’. Either of Van Basten or Gullit could do alone what Shevchenko and Kaka’ did together and, similarly, Rijkaard alone could boss an entire midfield.

          1. 👏 100% Carlo’s Milan also threw away matches, Dortmund, Deportivo. It was an excellent team but I always felt vulnerable with the midfield three. We lost in 2005 because Liverpool boss’s the midfield

            1988-92 Milan was an absolute machine, we were devastating, defensively gave nothing away, Rijkaard is probably the most underrated player we’ve ever had, Saachi always said he was the what of the three, he was the best defensive midfielder and attacking midfielder at the same time, he may well be the best Berlusconi signing of them all…

            That Milan was the best club side of all time, it would hbe defeated Pep’s Barcelona and Paisley’s Liverpool, everything Klopp and Pep do on pressing comes from that Milan team of Sacchi’s.

            For me if we are doing the 4312 the guys have suggested i put Pirlo in the midfield and it’s Gullit as the AM

            Also not a signing, but Demetrio Albertini was phenomenal

  4. Rossi over Dida every day of the week. Possibly the most underrated goalkeeper of the last 30 years. Dida always had a mistake in him, Rossi was commanding, great shop stopper and penalty save. He unfortunately started in the Zenga era, went through the Pagliuca and Peruzzi one and then Buffon came along.

    Can’t really argue with the rest though personally I’d have Pirlo in there though..

    1. Wrong. Dida didn’t ALWAYS have a mistake in him. He is unfairly remembered for a handful of mistakes, as for Rossi and mistakes, remember the Club World Cup? I seem to remember a high profile mistake in that game by Rossi.

      1. Well you’ve just defeated yourself there…Dida is remembered for a handful of mistakes…I don’t recall the Rossi incident you mention and I watched him from 1990 until his retirement

        The only way I can explain it is I always had nerves when watching Carlo’s Milan, for a number of reasons, and Dida’s potential to make an error. I NEVER had nerves watching Capello’s Milan.

        1. Yes, you’ve conveniently not seen Rossi costing us the CWC. A handful of mistakes doesn’t detract from Dida being excellent 99% of the time. He was mocked because he was a Brazilian goalkeeper, at the time Brazil wasn’t noted for producing great goalkeepers, Taffarel was crap.

          1. Not strictly true, Julio Cesar was good and Heurlho Gomes was decent.

            I’m not in any way saying that Dida wasn’t a great keeper, I just think that compared to Rossi he was more error prone. It’s an opinion. It’s literally a tit for tat argument. Plus Leeds United and the Bowyer incident happened before the flare incident so I don’t think that’s relevant

  5. I think I’m going to build this squad on FIFA just for old times sake. I’ll just have to make Maignan the goalkeeper since Dida’s not an Icon in FIFA yet.

  6. No mention of Lord Bonera? The greatest footballer the world has ever witnessed!
    But seriously, we had 20+ players who could easily be starters in any team at any point in history. For example: Pirlo, Savicevic, Albertini, Weah, Inzaghi, even Gattuso! And the more forgotten starts like Tasotti, Costacurta, Ambrosini, Bierhoff, Papin, etc.

    1. Papin was garbage for Milan. He was a big game bottler, he doesn’t belong on any list of Milan greats. Massaro did more for us.

      1. I was ecstatic when we signed Papin, he’s the player I always wanted, but you’re right, he underwhelmed for the large part. You can’t overlook that he did deputise well for the injured MVB in the 1992-93 season, and that volley in the CL against I think Porto.. he never hit the heights though

  7. I guess my ideal ‘Berlusconi’s Milan’ lineup would be a little different… well:


    Tassoti – Costacurta – Baresi – Maldini

    Pirlo – Seedorf – Rijkaard – Gullit

    Van Basten – Shevchenko


    Dida, Cafu, Nesta, Galli, Serginho, Gattuso, Boban, Kaká, Savicevic, Inzaghi, Weah

    1. A list made by someone who didn’t see half of the players from the 1990s. Seedorf was crap most weeks. He’s nowhere close to being one of Berlusconi’s best players. He had what, two decent seasons? Savicevic was the teams best player post Boban.

        1. It takes me back to those first few games of 92-93 when our bench had Boban, Savicevic, Simone, Eranio, Evani and Donadoni.. the 7-3 v Fiorentina, 5-3 over Lazio and the 5-1 over Napoli

          What a time that was. You never thought we’d lose, a draw was a bad result and it was how many are we scoring today…we were spoilt

  8. No no no it os not even near fair to line Cafiu over TASSOTTI.
    TASSOTTI is the best ever Acmiln RB.
    Sorry a free Transfer 35 yer old who because of we lost the 2005 UCL
    And then M ODDO won all UCL 2007.

      1. I agree, Tassotti gets overlooked because of Cafu. Sure Cafu was the invention of the modern fullback but Tassotti was legendary. His length of service and consistency also needs to be taken into account. It’s a tough call that. The name Cafu looks better on paper, but who would you want in the back 4….tricky

  9. The Berlusconi era gave Milan a meaning.
    With his trusted deputy, Adriano Galliani, the AC Milan strikes fear into every team, especially Man Utd.
    Rest on Pa Silvio, you will always be loved by milanistas.

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