All Time XI: AC Milan

If there was a series titled “Academy of Eternal Superstars” then the prime filming location would be the Milanello. There’s never been a more difficult All Time XI to select, yet paradoxically, never easier.

Since the first of fifty-one trophies was clinched back in 1901, the Rossoneri have defined football itself, exporting calcio abroad throughout three different eras as Il Diavolo’s domestic success transcended into continental glory during the 1960s, late 1980s to mid 90s, and early 2000s.

The pool of talent on offer for the Milan XI is more like an ocean rippling with footballing pedigree that is second to none.

Even though such a selection process is subjective, it also must be data-driven when splitting hairs between the world’s best ever footballers.

Goalkeeper: Sebastiano Rossi (1990–2002)

Perhaps Mike Maignan and Gigio Donnarumma possess the skills, however, it takes a goalkeeper of great courage — and a healthy splash of insanity — to scream obsessively at one of the greatest ever defensive backlines in European club history. Rossi won five Scudetti in eight years, including that unforgettable trifecta under Fabio Capello.

Let’s not underplay that 58-match unbeaten streak in the league between 1992 to 1994 which earned Capello’s team the label ‘the Invincibles’. Rossi also holds the record for the fewest goals (11) conceded by a goalkeeper during a single 34-match Italian league season.

Right-back: Cesare Maldini (1954–1966)

Before properly analysing this position, I’d been leaning towards Mauro Tassotti. In the end, it must be the man who pioneered Italian football’s crusade into adversarial European territories.

Cesare Maldini immediately broke into the first team at right-back in 1954, securing the first of his four league titles in his debut season. By 1961, Cesarone claimed the club’s captaincy ahead of Giovanni Trapattoni to lead Il Diavolo to its inaugural European Cup title in 1963 by defeating Eusebio’s Benfica at Wembley.

Milan became the first ever Italian side to be crowned European champion, while Maldini became the first Italian captain to lift the cup. A four-time Scudetto veteran of 412 games for Milan, Cesare retired from professional football in 1967 just in time to co-create the greatest left- back the world has ever seen.

Left-back: Paolo Maldini (1984–2009)

Simply put, Paolo embodies Milan’s soul. Born in 1968, Paolo signed on to play for Milan’s youth teams in 1978. That’s 31 years in a Milan shirt — or 16,293,600 minutes — with 25 consecutive Serie A seasons, a record for an individual player.

Having played under Arrigo Sacchi, Fabio Capello and Carlo Ancelotti, Paolo is Milan’s most decorated player with 26 trophies — more than half of the club’s sum total — including 7 Scudetti and 5 UEFA Champions Leagues.

Paolo was named as the best defender ever faced by Zlatan Ibrahimovic, Ronaldo and Roberto Baggio. Now serving as Milan’s technical director of football, he currently holds the club’s appearance record in both Serie A (647) and the Champions League (161).

Centre-back: Franco Baresi (1977–1997)

Another one club wonder that triggers palpitations in every Rossonero heart. Franco Baresi is a twenty-season veteran of the Milan senior side.

Ruthless in defence yet capable of carrying the ball forward, Piscinin (little kid) remained with Milan throughout the turbulent years of demotion to Serie B despite his elite status in the national team — a 1982 FIFA Champion — to provide stability and hope during Milan’s dark period.

After being handed the captaincy at age 22, Baresi excelled as a sweeping central defender and was seen as a tribal leader at the Rossoneri, retiring with a haul of 20 team titles including 6 Scudetti and 3 Champions Leagues.

Centre-back: Alessandro Costacurta (1987–2007)

Inducted into the AC Milan Hall Of Fame, Costacurta captured 24 trophies in 20 years at Milan for an extraordinary average of 1.2 titles per season — more than Maldini or Baresi.

Another disciple of the Capello-Sacchi reigns of the Silvio Berlusconi Empire, Costacurta took the reigns from Baresi in the centre of defence and helped steer the Milan ship as vice-captain until Alessandro Nesta’s arrival in 2002 where he formed part of Carlo Ancelotti’s backline that notched up another 6 pieces of silverware.

With hawklike vision and an amazing ability to launch balls forward, Costacurta made defending cool, refining it into an art form during 663 appearances for Il Diavolo.

Defensive Midfield: Demetrio Albertini (1988–2002)

Edging out Carlo Ancelotti, Frank Rijkaard, Massimo Ambrosini, Gennaro Gattuso and Giovanni Trapattoni for the anchor role in midfield is Demetrio Albertini.

Here we demonstrate how it’s never been more difficult, yet easier, to make the selection.

Exhibiting a world-class ability to read the game and a superb passing range, Il Metronomo (the metronome) emerged as a fantastic set-piece taker and boasted a long-range shooting capacity, contributing 28 goals for Milan and provided competent defensive cover.

Another product of the Milan youth system, Albertini debuted as a 17-year-old under Sacchi before being handed regular game time under Capello to form part of the invincible side that won the 1991–92 Scudetto undefeated.

Albertini served as the heir to Ancelotti and then Pirlo’s predecessor to become Milan’s most successful pivot, collecting 14 trophies along the highway to Rossonero glory.

Mezz’ala: Clarence Seedorf (2002–2012)

Milan is famous for Dutch legends Ruud Gullit and Frank Rijkaard but it’s Clarence Seedorf who flies the Oranje flag in midfield.

Dedicating the best decade of a glittering career to Milan, Il Professore was a multidimensional midfielder with faultless pedigree who offered a physical and intimidating presence on the park which could simultaneously win back possession and create goals from thin air.

Or score them. 62 stunning goals abetted Il Diavolo to feast on 10 trophies including two Scudetti, two Champions Leagues, and a FIFA World Club Cup to boot.

Additionally, Seedorf holds the record for most appearances for Milan by a non-Italian player (432).

Mezz’ala: Gianni Rivera (1960–1979)

The first of the four Ballon D’Or winners in this side, Gianni Rivera was acclaimed for his exceptional football intelligence as a centrocampista that could play in a deep-lying playmaker position, a mezz’ala role, or as a second striker.

Crucial in attaining Milan’s first ever European Cup title in 1963, ‘The Golden Boy’ is also Milan’s top Coppa Italia scorer in history with 28 goals, 7 of which won Milan the 1966–67 title and then subsequently the 1967–68 European Cup Winners Cup.

As the third highest goal scorer in the 123-year history of the club, L’Abatino also won 3 Scudetti, 2 Champions Leagues, 2 Cup winners cups and 4 Italian Cups throughout the sixties and seventies.

No10: Kaká (2003–2009, 2013–14)

The most recent Milanista to win the Ballon d’Or — ahead of Lionel Messi and Cristiano Ronaldo — Kaká was deployed by Ancelotti predominantly as a playmaking trequartista that sat behind the likes of Jon Dahl Tommason and Filippo Inzaghi.

The Brazilian’s impact was immediate with exemplary defence splitting passes, mesmerising runs and sublime goals that were simply out of this world, all which lasted up until his €68m transfer to Real Madrid in 2009.

Hopefully, Kaká’s trademark slalom run and finish against Udinese, his scorcher vs Anderlecht, and his solo goal to beat four Manchester United players will be perpetually exhibited to inspire future generations at the Milanello.

Striker: Andrij Shevchenko (1999–2006)

It takes a confident pair of feet to fill the boots of George Weah. And with the then world-record €25m price tag came pressure from the Italian media and high expectations from the Milan faithful.

Shevchenko let nothing stand in his way and silenced the critics by equalling Gunnar Nordahl’s 1949 heroics to become the Serie A top scorer in his debut season.

The Ukrainian fired in the crucial away goal against Inter in the 2002–03 UEFA Champions League semi-final and then clinched the title with an unerring shootout penalty to sink Juventus.

Shevchenko, who received the Ballon d’Or of 2004, is the second highest goal scorer for the Rossoneri behind Nordahl with 175 goals.

Striker: Marco Van Basten (1987–1993)

There are six Ballon d’Or recipients at Milan but only one of them has won it multiple times.

Three times in fact. 1988, 1989 and 1992. Of van Basten’s 128 goals for the Rossoneri, 87 of them were scored in those respective years.

Prodigious, freakish and so elegant that they dubbed him “The Swan of Utrecht”, van Basten lit up the peninsula to such a degree that Silvio Berlusconi opted to sack Arrigo Sacchi rather than his flying Dutchman after the two fell out.

With 22 goals in just 30 UEFA competition fixtures, van Basten spearheaded Il Diavolo to two European Cups, three Serie A titles and five other pieces of silverware. There is no denying this champion’s place in the Milan best XI.

Final Thoughts

As the Milan theme song says “Conquer another star to shine brightly for us”. I’ve no doubt that this Milan XI, which represents seventy years of decadence and domination, would conquer any Best XI club side you could name.

As I said earlier in the piece, the Milan Best XI is so difficult to pick yet picks itself.

Some of you might be bewildered at how a certain player doesn’t feature, however, apart from hours of research I’ve also consulted plenty of Milan fans that have followed the club for 50 years or more.

With Milan clinching their 19th Scudetto recently, one may feel that it’s harsh to discount the title winning team of 2022. However, considering that every starting Best XI player held a Scudetto AND Champions League trophy, it’s hard to argue that any of Pioli’s champions would feature in those teams of 1991, 2003, and 2007.