Which side was the premier’s best?

Back in February 1986, Milan were a completely different outfit from what they are today.

Giuseppe Farina, the owner at the time, was in dire financial straits and Milan were in crisis.

The last scudetto the Rossoneri had won when Farina was around was in 1979 and their most recent triumph in the European Cup had occurred a decade before. Indeed, the club had fallen on hard times.

Ironically, the best achievements of the early 1980s for Milan was winning the Serie B championship twice in 1980/81 and 1982/83.

But then came the advent of media mogul and future Italy Prime Minister Silvio Berlusconi and the club’s fortunes changed dramatically. In a short span of time, Milan became the benchmark and the envy of all other clubs, even those outside the peninsula.

Berlusconi’s first move was to poach great tactician Arrigo Sacchi from Parma and sign Dutch duo Ruud Gullit and Marco van Basten.

Berlusconi had spotted Sacchi in a Coppa Italia encounter in which unfancied Parma, then in Serie B, had given Milan a torrid time.

At first, most observers of the game were sceptical as to whether Sacchi was the right man to lead Milan out of the doldrums... time proved them wrong.

Milan soon ended a nine-year wait for a Serie A title. The 1988 scudetto was just the beginning of a golden era. Back-to-back European Cup triumphs, at the expense of Steaua Bucharest and Benfica, made of Sacchi’s Milan the team to beat.

During his reign, Milan were far more successful in Europe than at home. Successive triumphs in the Intercontinental Cup, in 1989 and 1990, were the icing on the cake in an era in which the club also lifted the 1988 Italian Super Cup and twice the European Super Cup (1989 and 1990).

After taking the club to such dizzy heights, Sacchi’s time at the San Siro came to an abrupt end in 1990/91 – a season in which the Rossoneri had finished empty-handed. Sacchi had fallen out with super striker Van Basten and Berlusconi showed the coach the back door.

Sacchi went on to replace Azeglio Vicini as Italy coach and his successor at Milan was Fabio Capello, another man chosen solely by Berlusconi.

In 1991, Capello’s track record was modest in having coached Milan’s youths and the senior side for a short interim period before Sacchi’s arrival.

However, with some tactical modifications, Capello transformed Milan into an even more formidable team.

He opted for substance rather than style and went on to lead Italy’s Red Devils to four league triumphs between 1991 and 1996 before leaving to join Real Madrid after a disagreement over the duration of his new contract.

The downside to Capello’s six-year stay on the Milan bench was represented by the upsets the team suffered in the Champions League finals of 1993 (vs Marseille) and 1995 (vs Ajax).

In between, the Rossoneri had hammered four goals past Johann Cruyff’s star-studded Barcelona in the Athens showdown.

With Capello as coach, Milan also lost two Intercontinental Cup finals, in 1993 and 1994, and the 1993 European Super Cup against Parma.

Capello was back to coach Milan in the summer of 1997 after leading Real Madrid to the Primera Liga title.

To his own admittance, that was an ill-timed return as Milan finished 10th in the Serie A.

Like Sacchi and Capello, Alberto Zaccheroni was an instant hit at Milan as he led the Rossoneri to an unexpected league triumph in 1998/99. At the time, the team to beat were Lazio as Milan were in a season of ‘transition’.

Still, Zaccheroni’s men defied the odds and went on to claim the club’s 16th scudetto.

This was merely a false dawning though as Zaccheroni was soon fired. A series of coaching changes – Zaccheroni, Cesare Maldini and Fatih Terim – were the prelude to another golden era for Berlusconi’s Milan.

Carlo Ancelotti was on the verge of making a headline-grabbing return to Parma when he changed itinerary and decided to replace Terim. The prospect of reviving the ambitions of a glorious club the calibre of Milan was too inviting for Ancelotti to turn down.

Sacchi’s influence

A sturdy midfielder in his playing days, Ancelotti had starred for Sacchi’s Milan and was his assistant at the 1994 World Cup in the US before he started professional coaching with Reggiana in Serie B, in 1995.

Like Sacchi, Ancelotti’s Milan reserved their best to the Champions League. As a matter of fact, the Rossoneri reached three finals – in 2003, 2005 and 2007 – and only managed one league success in season 2003/04.

In Manchester, in May 2003, Milan overcame Juventus in a penalty shoot-out.

To this day, this remains the only Champions League final contested by two Italian sides.

In Istanbul, two years later, Milan led Liverpool 3-0 at half-time but finished on the losing side after yet another shoot-out. That was the lowest ebb Milan had reached in Ancelotti’s eight-year reign.

Two years later, Milan made up for throwing away the 2005 final by beating the same Liverpool in Athens by the odd goal in three.

In 2003, Ancelotti also led Milan to the Coppa Italia. To date, this is the club’s only Italian Cup success in Berlusconi’s era. Ancelotti quit Milan to join Chelsea in 2009.

A quarter of a century has now gone since Berlusconi transformed Milan from an almost bankrupt organisation into the most successful club in the world.

It is difficult to choose the best Milan side of the past 25 years, albeit my inclination is to pick Capello’s 1993/94 edition.

Like the Inter teams coached by Helenio Herrera (1964/65) and Jose Mourinho (last season), that Milan team won the scudetto and Champions League in the same season.

To date, only these three sides have achieved this feat in Italy.