I can still remember exactly where I was when the dramatic events unfolded. My uncle’s living room, his giant satellite dish trained on the RAI signal as the game was played out. A scoreline still burned in the memory.
Milan 5 - Real Madrid 0.
How long ago it all seems now as that same fixture comes around again. Carlo Ancelotti, who scored the first and went on a clenched-fist run of celebration, has gone on a coaching tour from Parma to Juve to Milan to Chelsea. Ruud Gullit is a TV pundit. Marco Van Basten has flitted in and out of management, and Roberto Donadoni has been thrust into and thrown out of the Italy job.
Since that great day more than 20 years ago, the Rossoneri - like the rest of us - have gone through a lot of changes. They remain one of Europe’s most successful sides, of course, but they don’t strike fear into the hearts of opponents like they did under Arrigo Sacchi or, in a different way, Fabio Capello.
Nowadays, it's hard not to worry that the boys in red and black are facing a potential Waterloo every time they take to the pitch. Their ageing squad and mixture of gifted misfits means a disaster always appears to be just around the corner. Can they defy the odds once more on Wednesday evening? Or will they receive a “hell of a beating”?
The omens from the match in Madrid a couple of weeks ago do not look great. Milan appeared sluggish in comparison to a Real side full of vim and vigour. If they open up, the Spanish team might put them to the sword.
Some followers of the Rossoneri believe their coach, Max Allegri, has been given too rapid a promotion to such an important post. They would rather have seen him test his skills at a middle-tier club instead of making the leap from Sardinia to the San Siro. But they possibly forget that one of their greatest of all time, Mr Sacchi, made an even more speedy rise through the ranks.
There have to be questions, however, about how the Tuscan manager can cope with the enormous egos currently kicking around the Milan dressing room. Even more important is how he handles the club’s biggest personality, owner Silvio Berlusconi. It is an area of diplomacy in which Carlo Ancelotti was an under-appreciated and expert practitioner.
But beyond the strengths and weaknesses of Allegri, there needs to be an independent assessment of the players at his disposal. The addition of Zlatan Ibrahimovic and Robinho late in the day seemed like an 11th hour effort to add some clout. It has raised expectations among the support, but is it really enough to address this side’s deficiencies?
Kevin Prince Boateng seemed a more sensible introduction in many ways. Milan still have a lot of great ball players, but their biggest issue is getting them on the ball. The midfield enforcer seemed like an important addition in terms of building a platform for others to sparkle. But his use has been intermittent as the circus struggles to fit in all its big name acts.
A player like Andrea Pirlo sums up the Rossoneri’s difficulties. He still has great poise, vision and skill but gets snuffed out too easily by sides with a greater physical presence. The same can be said for Ronaldinho, Clarence Seedorf and others too.
What it means is that organised and energetic outfits (like Juventus on Saturday night) can get the better of the Milanese crew. They still have a crop of potential matchwinners, but too often they are unable to impose themselves on an opponent. Attacking players who rarely work back are a luxury few sides can afford.
It leaves the Rossoneri with an underbelly which is softer than a month-old banana unearthed at the bottom of the fruit-bowl. As the excellent Zonal Marking has illustrated, they are particularly vulnerable on the flanks. How they could use a player like Samuel Eto’o, who tracked back to such great effect for Jose Mourinho’s Inter last year.
And yet there remains something endearing about the Milan experiment. In a game which has got faster, stronger and fitter, they still stand for a different approach. A “no-look” pass by Ronaldinho, a skipping run from Pato or perfectly flighted 50-yard ball from Pirlo are joyous to watch. They use the epee where others strike with a sabre.
Will it be sufficient to fend off a Real Madrid side which already has a scent of blood? Or will the wheels fall off just as they did to their Spanish opponents back in the late 1980s? Whatever the outcome, it makes for an unmissable Champions League encounter. There can be few clubs in Europe that have as much to live up to.
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