Firsts, big breaks, friendships and memories: Looking back at 10 years of SempreMilan

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Ten years ago to this very day SempreMilan was born, and it feels like the right time for a bit of reflection and introspection.

Back on January 22 2016, we published our first article on SempreMilan.com. It was the comments from a pre-match press conference that Sinisa Mihajlovic did before a game against Empoli, and to this day we still cover every presser that takes place.

From those humble beginnings, something big came over the next decade. You can read more about how SempreMilan came to be in the origin story series we did on Substack, while earlier today we said our thanks to our amazing community for your support over the past 10 (we still can’t believe it) years.

What have been the high points and the significant moments? We tried to pull out the ‘best bits’ from SempreMilan’s first decade, and hopefully not last.

The first article

As we have already mentioned, article number one was nothing too crazy, rather something that was to become the staple of our coverage: the pre-match press conference.

Milan would frustratingly draw the first game since the site’s creation 2-2 against Empoli at the Stadio Carlo Castellani having led twice, a sign of the rollercoaster that was to come on and off the field.

From that piece came layers and layers of editorial standards that we have imposed both internally and externally (with SEO guidance) to create what we hope is a high floor when it comes to Milan coverage.

What was more exciting about hitting publish for the first time was that something dreamed up among friends just before a trip to San Siro for the derby against Inter (a 3-0 win, too) became reality. More on that in the origin story.

sempremilan first article

The first podcast

Fast-forwarding to June of that year, SempreMilan – more specifically Oli Fisher and Daniel Gutman – sat in front of a microphone for the first time to record a podcast.

Listening back to it almost makes us cringe, given how bad the audio quality is and the lack of chemistry between the two talking, something which we would come to correct over time (or so we hope!).

The subject of episode number one was to recap the 2025-26 season which had been another negative one for Milan, as they finished seventh and saw out the season with caretaker Cristian Brocchi.

To put it in perspective, the most recent episode was number 397, and there have been countless highs and lows between those.

Notable exclusives

One of the very first exclusives that we published back in our first year in 2016 contained some information from Pietro Balzano Prota (a collaborator at the time who is still going strong with his MilanVibes project) about Cesc Fabregas being a Milan target. It has been confirmed since that this was true.

Around that time we also managed to reach out to an agent – more specifically Thiago Maia’s – and get a first exclusive comment regarding a transfer operation. A few months later we would interview Primavera defender Marco Iudica.

In April 2020 came our first major story, as Yonghong Li chose us to break his silence over what went wrong towards the end of his time as Milan’s owner. It was a fascinating discussion conducted by then-collaborator Vito Angele, and one we are still proud to have published.

We have had many other bits of information over the years that we have circulated, but the one story we were well on top of thanks to knowing the right people was the signing of Jens Petter Hauge. We were the first to call his imminent arrival after his showing at San Siro, and Hauge’s name was back in the news recently after his heroics against Manchester City.

Back on 2 June 2023 we published probably our first big exclusive over on Substack (more on that platform to come) by revealing that Gerry Cardinale has scheduled a meeting with Paolo Maldini that could lead to his sacking. Sure enough, less than 48 hours later, Maldini had left the club.

Here we go!

Back in January 2021, the podcast reached a new level as SempreMilan were able to secure an interview with transfer guru Fabrizio Romano, leaving us a bit starstruck.

We asked him a number of questions about the present and future of Milan, the intentions of the ownership and certain players, plus possible targets for that winter window and beyond.

It was a true privilege to speak to somebody who is a huge brand in his own right, and someone who has become known the world over for delivering reliable information on transfers.

As fate would have it, Fabrizio became part of the network that part-owns SempreMilan further down the line, running a column which still stands (albeit not with him part of it anymore) called Daily Briefing.

Those fabled steps

The dream of every football journalist is to cover games live, especially when the team you love and have chosen to write about plays at a venue as iconic as San Siro.

However, the first time SempreMilan were granted press accreditation was actually for a game in a different country. More specifically, it was for a preseason game against Manchester United at the Millennium Stadium in Cardiff, Wales. It would be a 2-2 draw and a loss on penalties in the preseason under Marco Giampaolo.

The first game covered at San Siro was in the Scudetto-winning 2021-22 campaign as Isak Möller went to see that famous 3-2 comeback win over Hellas Verona. You could say that we brought a bit of good luck, but Covid had curtailed plans to get to a game in the media section earlier.

From there, we are fortunate to have seen many games from the gantry at the Meazza, from famous Champions League nights like Napoli at home to some more understated fixtures. It has also cultivated a positive relationship with the club, one we are very happy to still have.

The job has taken us away from Italy too, to places like Rome for the Coppa Italia final, as well as to England for Champions League games versus Chelsea, Spurs and Newcastle United between 2020 and 2024.

The middle of those three was the most enthralling, as Oli was part of a delegation of Milan employees and journalists who toured Tottenham’s new £1bn+ stadium, before then returning to cover the 0-0 draw which set up a quarter-final with Napoli.

The privilege of walking up the steps to the media gallery each time to cover our beloved team is something that we absolutely do not take for granted, and we thank Milan and other clubs along the way for being so accommodating.

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Glory at last

The only trophy that had come in the first few years of operations was the Supercoppa Italiana in 2016-17. While that triumph over Juventus was still something to celebrate, it didn’t quite have the feeling of being a major honour.

In 2021-22, everything changed as we covered the first title-winning season since SempreMilan’s inception. It feels like we all collectively aged 20 years in those months, but in the end it was worth it.

The celebrations that took place at Milan Club London – the pub from which Oli covered the 3-0 win over Sassuolo surrounded by hundreds of Milanisti – were unforgettable.

The podcast that the lads sat down to record after clinching Scudetto number 19 is also something we regularly look back on to lift our moods. It felt like a culmination in many ways, and that hard work across the board had finally led to being able to cover something truly special, as that team was.

Another string to our bow

Back on 1 February 2022, SempreMilan published its first ever article on Substack, which became the platform on which the vast majority of our bonus content would be published in the coming years up to the present day. It was a newsletter recapping the business done in the 2021-22 winter window.

Since then, the SempreMilan Substack has gone from strength to strength thanks largely to the work of Isak. His bonus articles each week take a deep and analytical dive into the hot topics of the moment, while the newsletter is something we have continued.

We have also made it a hub for additional video content too, such as bi-weekly episodes of Pub Chat featuring Stefano and Lorenzo, as well as the weekly Bonus Podcast episodes that Oli and Anthony record.

We are well aware that consumers of football content and media more generally are fed up of being told they have to access something. That is why we must first of all say a heartfelt thank you to those who have signed up for the Substack, and secondly we must strive to make it as good value as possible.

Things like the aforementioned Maldini exclusive is a good example of the priority and behind-the-scenes access that we offer there. You can try a week for free before deciding to join our amazing paying subscribers. Sorry for the ad, but you’ll forgive us, after all it is our birthday.

Social media growth

Starting from zero can be quite daunting, and nowhere is that more true than on social media. From the establishment of SempreMilan on various platforms like Twitter, Facebook, YouTube and Instagram, we realised how many giants of Milan coverage are out there.

Nevertheless, over the past 10 years we have grown and grown across these different fronts, and now we are immensely privileged to speak of followers in the hundreds of thousands.

We recently passed 150,000 followers on X (formerly Twitter) which feels gigantic. On Facebook we will soon hit 100k, YouTube is now over 11k and Instagram will soon pass 20k.

We’ve never really cared for social media counts too much nor the concept of ‘going viral’, but seeing numbers like these makes us feel truly humbled because it reminds us of the sheer size and scale of the community we have welcomed.

Friends along the way

An important closing point is to remember that this project and labour of love all started because of some friends who had a shared passion for AC Milan. Those friendships haven’t changed or faded – if anything they have only gotten stronger.

At various points in the past few years members of the SempreMilan team have gotten together to watch games, share a few beers and reminisce over times good and bad. We all speak every day, and these are bonds that wouldn’t have come about otherwise, while they will last for life.

Also, if you are one of the many people who has stopped one of us for a chat at a club or at a game, thank you too. SempreMilan was formed to create these connections and unite us all under the red and black, so thank you. Here’s to another 10 years, and possibly many more.

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