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Roma v. Milan: An Insider’s Look at the Rossoneri

Milan Club Philly is back again to talk about all things Milan ahead of Sunday’s match at the Olimpico.

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AC Milan v AS Roma - Serie A Photo by Giuseppe Maffia/NurPhoto via Getty Images

Last year, Milan Club Philadelphia (@MilanClubPhilly) president, David, was nice enough to spend some time giving us an insider’s look at the Rossoneri. David was pressed for time due to work this time around, but his VP, Maurizio, was nice enough to let me pick his brain in David’s stead.

Maurizio provided more great insight on all things Milan ahead of Sunday’s match at the Olimpico. With both teams in “Year Zero” of their respective projects, this interview reminds us that Roma isn’t alone in its struggle to keep up with the Jones’ (aka Juve, Napoli, and Inter).

So, read on to get an insider’s look at all things Milan. And if you’re in the Philadelphia area join both fan clubs for a joint watch party.

1. What were your expectations for Milan heading into the season?

Maurizio: From a sporting perspective, finishing top four and returning back into the Champions League. Stylistically, I wanted to see the team to play with an identity. This season was supposed to be another fresh start with a new leadership team, new manager (Marco Giampaolo), and new young signings (Bennacer, Krunić, Theo, Leão). We opted out of the Europa League to pay FFP repercussions from years prior, so arguably we were the only top four competing team that didn’t have extra midweek Champions League/Europa League matches.

2. What was your initial reaction to the Giampaolo hire? Why do you think it went so wrong?

M: I had mixed feelings on the Giampaolo hire. Optimistically, I was excited that Milan finally hired an actual manager, and not just a former player. A manager that was heralded as a “tactician” by his peers and the media (Arrigo Sacchi went as far as calling him a maestro). Pessimistically, I had some doubts since he never coached a top club prior to Milan, and he didn’t have the greatest win percentage.

After four horrible defeats and three unconvincing wins, I’d say everything went wrong for Giampaolo. What was most telling about his failure was the team looked disoriented and clueless under his “system,” as if they had never played with each other. They never looked dangerous or convincing. Giampaolismo was never to be seen, let alone created. Giampaolo is a system manager who needs system players, and unfortunately, he wasn’t granted enough time to achieve any of this. Personality-wise, he never seemed confident on camera, in press conferences, or sitting on the sideline. Pioli seems to be the polar opposite.

3. What about the squad gives you hope that the squad can reach your original expectations?

M: I’m not fully convinced with Pioli replacing Giampaolo quite yet, but I’ll give leadership the benefit of the doubt for this being a short-term solution. I’d like to see the players truly prove their worth to play for a club like Milan. There are some players who’ve been under scrutiny from fans (Suso, Çalhanoğlu, Conti). If these guys rise to the occasion and prove the doubters wrong, we could still very much make top four. Aside from that, the season is still open and there are many games left to play. Who knows, maybe Atalanta, Roma, Torino, and Lazio may slip up as well. I think it’s safe to say the top three will be Juventus, Napoli, and Inter (in no particular order).

4. Conversely, what do you see as the biggest flaws of this team?

M: Milan is certainly far from being the perfect club. From an ownership perspective, without looking too much into previous seasons, we’ve had organizational instability since the very end of the Berlusconi/Galliani days, through the Fassone/Mirabelli season, and now the Elliott era. Alongside this, we’ve had seven different managers since Allegri was sacked back in 2014, and countless “banter” players joining the team (anyone remember Bakaye Traoré?). All of this has adversely affected the team’s performance on the pitch over the years.

In regard to this season, one of the biggest flaws of this team is a lack of senior leadership. For better or for worse, Milan is a young team—and that is the vision Ivan Gazidis has for the club moving forward. As such, we lack the senatori of previous years on the pitch and in the locker room. Pepe Reina and Lucas Biglia are the oldest (and most experienced) players on our current roster, but they haven’t really shined on the pitch since joining the club. And then there’s Giacomo Bonaventura, who’s a fan favorite, but has been plagued with injuries. Through time, I hope to see players like Alessio Romagnoli and Gigio Donnarumma step up and become leaders at the club.

5. Roma and Milan have both struggled to get their projects truly up and running in recent years. What has caused Milan’s delays?

M: The simple answer is found in your question: delays. The beginning of this season saw delays in confirming Maldini, Boban, and Massara to the leadership team, which led to delays in confirming our participation in Europa League or not. Next, we saw delays in officially hiring Giampaolo, which delayed critical player signings and time for the team to get acquainted under his system. For the last few seasons, we’ve begun at “Year Zero” and things look to be the same for this season. Let’s see what #PadrePioli can do.

6. What do you think the future holds for Milan? Ownership, stadium, management, FFP, etc.

M: I truly believe Milan is making strides—albeit slow ones—to build a better future for the club. Elliott, Ivan Gazidis, and friends really inherited a mess from the previous Silvio Berlusconi and Li Yonghong ownership groups. I hope the leadership team in place stays and builds upon the foundation they create season-to-season. Finishing top four is so important for this club to earn the Champions League revenue and recruit top players (and retain current players). FFP is always a hot topic for a club like Milan, but only time will tell if we need to sell players to balance the books.

The stadium situation is bittersweet. On one hand, you want the San Siro to live forever, but as much as I love the San Siro, I fully support building the new stadium. It’s time to bring the club (and Italian stadiums as a whole) into the 21st century. We recently did an in-depth discussion and analysis with Milan Weekly Podcast (@MilanWeeklyPOD) and other Milan Clubs from Montreal and Australia. You can check that out here.

7. How do you see Sunday’s match playing out?

M: Although we drew against Lecce last weekend, we played better under Pioli in those 90 minutes than we did for Giampaolo’s entire seven match stint at the club. Milan deserved to win that match, but lapses in concentration unfortunately left us with a draw.

Roma will have a lot to play for given the last three disappointing (and controversial) draws against Cagliari, Sampdoria, and Borussia Mönchengladbach, but the team is still coping with crucial injuries. I honestly think it’s a 50/50, but I’m going with a Milan win. Both teams will score goals—let’s see which side scores more.

Regardless of the outcome, I want to shamelessly plug Gran Caffe L’Aquila (@GCaffeLaquila) in Philly for hosting both Milan Club Philly and Roma Club Philadelphia this Sunday. It’s a hot spot for Calcio in Philly—and the food, drinks, and gelato are amazing!