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The Milan Derby – How I Fell In Love with European Football and Out of Love with a Woman

Updated: Apr 21, 2023

On a muggy spring night in Milan in 2001, my love for a woman waned just as I began a lifelong love affair with football. Like most of my fellow Americans, I knew it as soccer, which was way below the radar of the four other major American sports of baseball, football (the other kind), basketball and hockey. Sure, I had been soccer curious for a while.

Like dozens of other Chicagoans, I marveled when my hometown Chicago Sting of the now-defunct NASL won the “Soccer Bowl” in 1981 and 1984. I also closely monitored the World Cup in the USA in 1994 when the upstart Alexi Lalas-led American team shocked the football establishment by making it out of the Group Stage. Yet, I had never witnessed a “real” football match in person until the night I attended a historic Derby della Madonnina at the San Siro in Milan, Italy. That match changed the trajectory of my life on both a sporting and romantic level.

The Duomo of Milan dominates the center of the City. Look closely in the bottom right photo for a view of Milan’s other cathedral punctuating the horizon – the San Siro stadium.

My long-time girlfriend and I were at the end of a European journey on the rails to usher in my 30th birthday. Throughout that trip, I wrestled with the notion that leaving my 20s behind meant that I was scheduled to become an adult. This trip was meant to ease my self-pitying pain and included stops in Prague, Budapest, Vienna and Venice. For airline logistical reasons, we ended our trip with a brief stay in Milan.

Left to Right: Prague, Czech Republic; Budapest, Hungary; Vienna, Austria; and Venice, Italy

The Milan leg of the journey was a mere stopover that would include great food and, per my companion’s not-so-secret plan, intense shopping in one of the fashion capitals of Europe. When we arrived at our hotel, I glanced through an Italian newspaper and discovered that Inter Milan and AC Milan would play their Derby (a rivalry game and pronounced “dar-bee”) the next day.

Before the days of global football teams having glitzy websites in 6 languages, trying to decipher an Italian sports section was the only way for me to learn of my fixture fortune (a “fixture” is a scheduled match in soccerese). My dream of seeing real football would finally come true, with a MAJOR match at the San Siro stadium as an added bonus, Turning 30 was looking better. Through the hotel’s helpful staff, I waaaay overpaid for 2 nosebleed tickets from a broker and convinced my girlfriend that we MUST attend this match. She never really understood my sports fandom, but reluctantly agreed to accompany me on account of…ya know…the big “whoa is me” birthday.

As I was reminded many times, central Milan is a major fashion and shopping destination.

As the hours before the game ticked away, I tingled with excitement. The city center of Milan was overflowing with humanity both with anxious football partisans and supports of Silvio Berlusconi (AC’s then-owner) rallying before the pending election. With the intense buzz overtaking the Piazza del Duomo, I itched to get to the San Siro asap to absorb the pregame atmosphere.

Yet, as a “compromise”, I reluctantly agreed to join my girlfriend for a “quick” shopping (her pastime) in the Via Montenapoleone fashion district before the match. Little did I know, she would spend over TWO flipping hours looking at fancy bedding at Frette and Anichini while I slowly realized that our ample pregame time was disappearing. In the days before smart phone distraction, I paced back and forth wondering how the F&#@ the Italian snazzy sheets would even properly fit an American-sized bed. After wasting almost two hours closely scrutinizing fabric patterns, the compulsive super shopper inconceivably reversed course at checkout and decided she no longer “needed” the 25,000 thread count sheets.

But I digress… Although I could not dig out any photos of the Frette and Anichini linen shops from my old negatives, the above pics are of the exquisite Galleria Vittorio Emanuele II shopping arcade next to the Duomo. I must admit that this shopping venue is well worth the visit to admire the stunning architecture that dates back to 1865. Because I am often a sophomoric child, my favorite quirk of the so-called “Drawing Room of Milan” is the bull mosaic on the floor beneath the central dome. It is purportedly good luck to spin on one’s heel on its testicles (more often “bull’s balls”) three times counterclockwise. As a result of millions of heel spin castrations, the divot in the Bull’s groin is as deep as a post-winter Minnesota pothole.

The Galleria Vittorio Emanuele II shopping arcade has amazing architecture, top fashion brands and the lucky “bull’s balls”.

We then raced from Milan’s “Golden Quadrilateral” and dodged rallying Berlusconi thugs to board a bursting Metro train. Once we exited the Metro station, we a packed ourselves into a shuttle bus that dropped us off a long walk away from the San Siro. We were finally on the stadium’s grounds and were… VERY F’ING LATE!!!! As we scrambled to our gate, the crowd noise bursting from stadium was practically mocking me for foolishly missing the start of this huge match for fricking sheets!!! To make the wound salty, I later learned that we missed amazing pregame TIFO displays by both Ultras and the match’s first goal too. While I was thrilled to be at this match, I still seethed that my girlfriend’s selfishness caused us to miss some of the coolest parts of the experience. In the big scheme of things, of course it was not super important, but still stung in the moment.

Left: Before the days of digital smartphone entry, ticket stubs were works of art.

Right: The walk to San Siro past loads of future treasures at souvenir stands.

After I got over my clinging-to-my-20s petty anger, I was totally and completely BLOWN away by the match at the San Siro. The official name of the 80,112 seat stadium is Stadio Giuseppe Meazza (opened 1926) and is home to both A.C. Milan (officially Associazione Calcio Milan) and Inter Milan (officially Football Club Internazionale Milano). It has hosted the FIFA World Cup in 1934 and then was expanded for the 1990 World Cup. Like the old Cowboy’s Texas Stadium in Irving, TX it has a hole in its roof making it a semi-enclosed caldron of noise. The intensity of the sound was unlike anything I had ever heard.

Sure, I had been to big rivalry games in the States. I live in Boston and had witnessed bitter Red Sox battles against the Yankees at Fenway. I was the Photo Editor for the Michigan Daily student newspaper in college and have experienced Michigan vs Ohio State football at that cesspool in Columbus. As well as seeing the Fab Five vs Duke in the NCAA Final. Nothing compared to the total bombardment on my senses that resulted from the Milanese civil war at this aging arena. Deafening singing and chanting continued unabated throughout the match. Despite not knowing what they were saying, you could feel the intensity.

San Siro was a non-stop cauldron of sound, color and fury, with non-stop singing and chanting.

Left: Texas Stadium in Irving, TX, home of the Dallas Cowboys from 1971 to 2009, which was reminiscent of the San Siro with its open roof.

The noise was constant. The stadium shook with jumping fans. Despite being the “home” team, Inter feebly defended that status against A.C. The match turned into a famous 0-6 drubbing of Inter by A.C Milan, including two goals by the Ukrainian legend Andriy Shevchenko at the peak of his footballing powers. This A.C Milan team was loaded with star players. Gianni Comandini, Serginho , Paolo Maldini, Gennaro Gattuso to name a few. This game was so huge that it was refereed by star official Pierluigi Collina.

The stadium’s air reeked of sulfur from all the flares following each A.C. Milan goal, which started to obscure the pitch with smoke. The singing and chanting never stopped. It was menacing, operatic and exhilarating. Given the scoring barrage, I could only imagine how loud the San Siro would have been had it been an A.C. Milan “home” game instead. It was nominally a home game for Inter, with seventy percent of the supporters being Inter fans glued to their seats in misery. Despite being the minority, the A.C. Milan fans created more noise than a packed concert and NFL stadium combined.

Six A.C. Milan goals delighting their supporters, with the hardcore ultras lighting flares after each score. The smoky arena reminded me of the infamous 1988 Fog Bowl NFL Playoff game betweeen the Eagles and Bears at old Solider Field in Chicago (bottom).

When the smoked had cleared, I was hooked for life. I determined then and there that I would see as many live football matches as I could. After seeing how passionate the fans in Milan were, I could not believe that I wasted so much of my life thinking that American sport rivalries were “intense”. I also resolved that I would not let something like a pampered girlfriend’s sheet shopping stop me from my football quest.

Author’s Note: For what it is worth, there were a slew of other non-sporting issues plaguing the relationship, but work with me here for the sake of football.

The shopping-obsessed woman would soon be out of my world, but my football love has continued unabated. Shortly after attending the Milan Derby, I became an Arsenal supporter after (1) reading the book “Fever Pitch” by Nick Hornby, (2) becoming infatuated with Highbury Stadium (Arsenal’s former historic ground in North London) and (3) when I realized that Gunner’s striker Thierry Henry was Michael Jordan in football boots (cleats for the uninitiated). I also have come to admire and follow a few other teams such as FC Barcelona (before Messi arrived), Portsmouth F.C. on the South Coast of England (Pompey for short) and the Portland Timbers of the MLS.

Counterclockwise from Top Left: Arsenal’s star-studded squad from 2002 (who would form the backbone of their undefeated “Invincibles” season in 2003-4); Arsenal Stadium (more commonly known as Highbury), the Gunner’s ground from 1913- until 2006); Opening Night Tifo at the Portland Timber’s Providence Park in Portland, Oregon created by the incomparable Timbers Army.; Portsmouth FC (aka Pompey) during a Premier League match against Man City in 2004 at aging Fratton Park; Camp Nou stadium, Home of FC Barcelona, during a tour in 2010 FC Barcelona defensive legend Carles Puyol takes on Juventus’ Edgar Davids in a 2003 Friendly at Gillette Stadium in Foxboro, MA.

Like me, the States has evolved and football has become MUCH bigger since 2001. With the advent of streaming, I can now watch every English Premier League game live. Additionally, supporters groups have flourished across the U.S. and my local Boston Gooners supporters group packs hundreds of fans into pubs for big matches. When Arsenal broke their long silverware (trophy) drought in 2014, jubilant Gooners stopped traffic on Boylston Street in the Back Bay as we celebrated winning the FA Cup.

I now am married to a wonderful woman who does not exactly love footy, but gladly will join me for a match every time we go on a trip overseas. We always get there early enough for kickoff and a pre-match pint or two or three. I also have made some great football loving friends along the way. We have made various pilgrimages to Europe and around the States for football trips. These include a cold rainy Friday night on the Kop at Notts County; Arsenal’s Carling Cup debacle at Wembley; Oktoberfest in Munich combined with two Bundesliga matches; and the US Men’s Soccer team’s Copa America triumph in Philly.

I even travel hours on Amtrak to watch live recordings of the suboptimal “soccah” podcasters known as the Men in Blazers. Best yet, I now have two sons that have become soccer curious and joined me for matches at London Stadium, Vicarage Road Stadium, Brammall Lane, and Camp Nou just to name a few. Photos from those trips and many others from the last two decades are below. Who knew that a historic blowout AC Milan victory, and a doomed Italian linens shopping trip, could be so life transformative?

All photographs and text by Ken Smoller. ©1986-2023 Stadium Vagabond – All Rights Reserved.

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