Sunday, November 02, 2025

Milan-Roma Preview: For the Money

Just a month ago, Milan had defeated Napoli to go top of the table. Since then, they have had three draws, dropping six valuable points. Now, they are fighting just to stay in the top four as they host Roma, who come into this weekend joint top of the table themselves. For Milan fans, this match is a tough sporting challenge, complicated by the numerous injuries the squad have been dealing with. However, for Cardinale, Sunday is a marketing opportunity. A chance for his €1.3 billion marquee investment to help promote a product of his 1.8 billion investment in a struggling media and entertainment company. For Gerald, this one is for the money.

It's not about the football, it's about the billionaire getting more money.

Poor Roma are probably under the delusion that they are traveling to the San Siro for a football match. Their new manager, Gasperini, spent nine years at Atalanta, with everyone questioning if he could ever make it at a bigger club. Now, having been chosen by last year's manager, Claudio Ranieri, who has stayed on as a Senior Advisor to the Roma owners for sporting matters, Gasperini is answering those people. Yes. He can make it at a bigger club. In fact, even Roma, who are always second at best, are better off with him. Which is terrible news for those of us who hate Roma.

Hey, I remember that guy on the left... wasn't he in a lot of pictures with Maldini or something?

Of course, we just met Gasperini's old team on Tuesday, who are managed by the guy who Claudio Ranieri replaced last year at Roma... you can't make this stuff up. Also, Roma's Sporting Director (again) is our former Frederic "Ricky" Massara, from the good old days. Massara is back for his third spell at Roma, and Gasperini has them flying, with their most recent win being a 2-1 win over Parma on Wednesday. For that match, Gasperini lined up a 3-4-2-1 with: Svilar; Mancini, Ndicka, Hermoso; Çelik, former Milan wantaway Cristante, Koné, França; Soulé, Dybala; and Ferguson. Gasperini will be missing Angeliño and Ferguson, who was injured in Wednesday's match.

Allegri got some great news this week as Jashari finally returned to training after his long injury. Estupiñan also returned after his injury sustained while on national team duty last month. While Jashari is unlikely to actually play, and even Esuptiñan's participation will be limited at best due to their time off, it is always great to welcome players back from injury. It would be even better if we were not also sending more players to the training table at the same time.

Look who's back in training! Our favorite Swiss Milanista!

Leão, Santi Gimenez, and Tomori all came off the pitch with issues during Tuesday's match. Leão returned to training and is cleared to start. Miraculously, Tomori has been called up for the Roma match, although how much he participates is unknown, as he trained little or not at all with the group this week. However, Santi Gimenez is definitely out for this match with an ankle issue. He joins Pulisic and Rabiot as the three last players Allegri is missing completely to injury. (And also Balentien, I believe as well.)

To cover for the missing players, De Winter will almost undoubtedly start in place of Tomori, while it is expected that Bartesaghi will at least start in place of Estupiñan, particularly with how well he has played in his absence. It is reported that Allegri has also called up 17 year-old Sala once again and also 19 year-old Diego Sia from Milan Futuro, as well as 18 year-old Castiello from the Primavera (he also played for and scored for Futuro midweek.) They have all been training with the team, but Castiello seems to be the only one actually called up for the match, which is good news for Oddo, who is already facing so many missing players.

An in-form Primavera striker, Castiello, is the one Allegri has apparently called up for this one.

But I digress. I have only talked about the sporting merits of this match, and Gerald Cardinale has made it very clear that competition "isn't rewarded financially." I suppose that's why he bought a team in first place in Serie A, took them down to eighth place, and brags about having spent more than any other team in the league in the summer transfer window. 

He also takes credit for the positive balance sheets that have been handed to him by the sporting sector of the previous management: first, the deep run into the Champions League that led to Milan's first positive balance sheet in decades. Then, selling off the players that management had invested in and developed for big profits to maintain a positive balance sheet once again. But obviously, Gerald knows everything about sport, football, and Milan. That's why he knew that Milan was so decorated in the Champions League nine months after buying the club. Oh wait, he didn't. My bad.

I wonder if Gerald even knows this guy's name? (Welcome back, Estupiñan!)

So, in his quest to reward himself financially instead of make Milan competitive, Gerald coordinated this match with the promotion of a new Paramount movie that is being released next week. (Nevermind that it's a violent rated R movie based on a Stephen King novel being promoted in a stadium promoting family attendance from a "family club.") And, with RedBird as a major investor in the recent merger of Skydance and Paramount, and a board member of both Paramount and AC Milan, this benefits both of his investments. 

He literally said, "you have to be able to pay yourself." And he is narcissistic enough to believe that he is the one with the knowledge to take 125 years of Milan history and 113 years of Paramount history and "rewrite" these brands. Even though he hasn't even attended a Milan match in over a year and has no knowledge of or even interest in the sport. (And let's not talk about the fact that his experience in the entertainment industry is highlighted by attending JLo's Birthday party.) Basically, he is using the Milan brand to promote a new movie from his other company. That's not genius, that's just a lack of morals.

They're already running for the survival of their careers, they play for Gerald Cardinale.

So, while on the pitch, 22 players will be battling it out in a clash of what should be two top four teams this season, the real purpose of this match is to drive income for two of Gerald's investments. Gasperini is looking to establish himself as a winning manager at a club that never actually wins, and Allegri desperately needs a career reboot after leaving his last job so badly. Both teams have players hungry to score and to win. Certainly, their level of competition is rewarded financially. And the fans only reward the clubs financially based on the clubs' ability to compete, because that is what sport is actually about. But clearly, like a bad Paramount movie where people are hunted and killed for sport, none of the stakeholders actually involved understand what this match is really all about, it is clearly only for the money.


This post inspired by the music of The Math Club's "Gimme That Money (Main Title Theme)"


Our next match is:
Campionato Primavera 1 Week 10
Lazio Primavera vs. Milan Primavera
Sunday, November 2, 2025 • 11:00 CET 5am EST*
This match is not being televised in the U.S.
* Note the end of U.S. Daylight Savings Time




Serie D Week 10
Milan Futuro vs. Oltrepò
Sunday, November 2, 2025 • 14:30 CET 8:30am EST*
This match is not being televised in the U.S.
*Note the end of U.S. Daylight Savings Time




Serie A Week 9
Milan vs. Roma
Sunday, November 2, 2025 • 20:45 CET 2:45pm EST*
In the U.S., this match can be streamed for free on DAZN (in Spanish,) or on Paramount+,
or use a VPN to access better coverage
*Note the end of U.S. Daylight Savings Time