A bright red scooter skids by and the evening fireflies take flight. Springtime has spread itself across Milan like an open palm, and by some trick of the light San Siro is bathed in a magical purple glow from every direction. Climb one of the epic spiral walkways at just the right moment and your reward is one of the great sensory overloads in European football, a place that feels closer to heaven than Earth.
In the distance, the Milan skyline blinking and twinkling in the setting sun. In the foreground, the swell of noise and the smell of narcotics and the billow of flags: black and blue, black and red, delete as appropriate. Another night singing hymns. Another night chasing dreams.
Then a whistle blows and what follows is – frankly – not great. Milan, resting half a dozen first-team players, are trying and largely failing to break down Cremonese, who are trying and failing to stave off relegation to Serie B. As Divock Origi runs into dead ends and Charles De Ketelaere keeps tripping over the ball, the Milan faithful begin to grumble.
A man in a Wu-Tang Clan T-shirt swears loudly in between sucks of his vape. An injury-time equaliser from Junior Messias salvages an unlovable 1-1 draw. Two hours up the road, their city rivals, Internazionale, have crushed Verona 6-0 to move ahead in the Serie A table. Napoli are 15 points clear and playing the following night. This is Milan’s last night as champions and nobody quite knows what happens next.
The following morning, a Milan club employee who for obvious reasons must remain nameless is telling me he is desperate for Manchester City to win this season’s Champions League, just so Inter do not. “The final will be Manchester City against Inter,” he declares glumly. “In this moment, Inter are stronger. Only Pep Guardiola can help us.”
Most of the Inter fans I speak to are a little more optimistic about their chances, but make a similar admission: the anticipation of victory is vastly outweighed by the dread of defeat. “I have a sick feeling,” says Alfio, an Inter fan in a distressed leather jacket buying Pall Malls near the canal. “To lose to Milan in the semi-final, after 20 years, will be the most horrible thing.”
Perhaps all derbies are this way to a certain extent. But of course this is no normal derby: a Champions League semi-final, two legs over six days that will subsume an entire city in red-on-blue psychodrama.
It is the biggest Milan derby in two decades: a local soap opera playing out in front of a global audience, a game of old romances and new anxieties.
The stakes are almost unthinkably high. Unlike with City or Real Madrid, there are no guarantees either team will qualify for next season’s competition. To lose would be crushing enough; to do so against their sworn enemies adds a quantum of terror that neither club can fully contemplate. Small wonder Alessandro Nesta, a veteran of the classic 2003 semi-final that Milan won on away goals, is predicting an ugly, conservative game. “The two teams fear each other,” he said.
Neither club is in the best shape. For Milan the draw against Cremonese continued a miserable run of just three wins in 12 games since the start of March. Any remaining fumes of a title defence disappeared after the World Cup break. “After January there was no consistency to fight,” the coach, Stefano Pioli, admitted. And so in a season of strife, the Champions League has thrown them a life raft: a chance to reclaim not only some pride and silverware, but a piece of themselves.
It’s hard to overstate the importance of this competition, and those seven victories between 1963 and 2007, in constructing Milan’s sense of self. At the club museum, visitors are greeted by a giant three-metre replica of the Champions League trophy. “When you join AC Milan you understand that the DNA of the club is the Champions League, the European Cups, the tradition,” says Filippo Inzaghi in a recorded video. The club’s rich and gilded history is lovingly curated and chronicled and brought to life. Until 2011, when the exhibit abruptly stops.
Outside the museum, chatting to a Milan fan from nearby Monza, I make the mistake of suggesting that this semi-final is a good thing for the city as a whole, a welcome boost for Italian football, putting these two toppled giants back on the map. He sniffs in disdain. “It’s good for us,” he says. “Inter can go fuck themselves.”
The Milan/Inter rivalry is a strange one. There is no real ideological, sociological or geographical divide between them. They even share a stadium. Their fans are pretty evenly spread across the city: neighbourhoods and workplaces and schools and often even families divided along tribal lines. For all the fire and fervour of the two clubs’ ultra groups, derbies generally pass off with very little incident.
“There’s no hate in the Milan derby,” Andriy Shevchenko once said and, while Wednesday night will test that statement to breaking point, generally it holds true. Ask fans of both clubs who they genuinely hate and the most popular answer will be Juventus.
“We’re dreamers,” says Luca, a Milanese native who has just moved back to the city after almost a decade helping to organise the London branch of the Inter fanclub. “We want to win, but not at the expense of rules and fair play and style. Go back through the history of Inter and you’ll find big highs and big lows. An Inter fan is never happy. But we’ll still always support the team, no matter what.”
One of Luca’s earliest footballing memories is of Inter signing Ronaldo in 1997. He was about six years old. He clearly remembers his father coming home from work and announcing, as calmly as possible: “We’ve signed the best player in the world.”
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These were the days when Italian football was the envy of Europe and this city felt like the centre of the footballing universe, when the Milan derby was like a roll call of world greats: Ronaldo, Shevchenko, Weah, Seedorf, Pirlo, Vieri, Crespo, Rui Costa, Rivaldo, Maldini. It all culminated in the 2003 semi-final: those heady May days when, as Gazzetta dello Sport put it: “The city has never felt so much electricity for football.”
Nesta remembers the silence before: the way even big personalities such as Massimo Ambrosini and Gennaro Gattuso went sullenly about their business all week, the sheer tension and stress eating away at them. Luigi Di Biagio remembers the silence afterwards: the stillness of the losing Inter dressing room, broken only by sobs. He didn’t sleep for several nights. “I spent four wonderful years in Milan,” he would later remember, “but that was the only time I really felt the derby. Tensions, pressures, expectations. Everything came from outside. It was impossible to turn a blind eye.”
In retrospect, it was something of a high-water mark. The good times would continue to roll for some years: another Champions League crown for Milan in 2007, an unforgettable treble for José Mourinho’s Inter in 2010. But the seeds of decline were already being sown. The Berlusconi and Moratti dynasties who owned the two clubs were beginning to scale down their ambitions just as everyone else in Europe was scaling theirs up.
In 2015-16, for the first time in 60 years, neither side was represented in Europe. A revolving door of owners put Milan on the brink of bankruptcy. Inter struggled and stagnated under the new ownership of the Suning Group. Managers and mediocre players came and went. Inter went six years without Champions League football, Milan seven.
This was once one of Europe’s great footballing cities, the only city to boast two European Cup winners. Yet even now, as you walk the weathered, peeling, majestic, history-soaked concourses and staircases of the Stadio Giuseppe Meazza, it’s tempting to wonder whether it is still true.
The last few years, admittedly, have seen something of a revival. Inter recaptured the scudetto under Antonio Conte in 2021; Milan followed them under Pioli last year.
There are signs that both clubs are beginning to emerge from the financial wilderness: Inter via a possible sale this summer, Milan with a concerted programme of debt reduction under the ownership of the American private equity firm RedBird Capital. And now a two-legged semi-final that will stir the senses and memories, even if it’s hard to envisage it producing a potential champion.
Yet Italian football remains in a precarious place, bearing the scars of underinvestment and neglect, choking on the dust of the Premier League. Neither club is really in a position to sign the world’s best players; on the contrary, Milan will have to fight to keep Rafael Leão this summer, while Inter are already resigned to losing Milan Skriniar to Paris Saint-Germain.
None of what happens over the next couple of weeks will really change any of this. And yet as kick-off approaches on Wednesday night this city will come alive again: still singing, still hoping, still dreaming.
