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Milan-Roma Preview: The Prodigal Son

Not only did Montella play the best years of his playing career for Roma, but he also started his managerial career there. They gave him so much. Yet he claims to be a lifelong Milanista, and his passion for the red and black is obvious, no matter what criticisms anyone has of him. Speaking of criticism, this match he is like the Prodigal Son in more ways than one. With Milan having spent so much this summer, Montella comes to the San Siro having dropped points in the league twice, while the favorite Champions League brother, Di Francesco, has a game in hand and only lost once (albeit to Inter.) No matter which way you look at it, Montella comes into this one as the Prodigal Son.

All eyes are on the ex-Roma player and coach

Roma are Scudetto dark horses this season. Although we all know that Roma never win. Still, a top three finish is likely expected of the former Sassuolo magician, Di Francesco. So far, they have done well enough in the league, but it remains to be seen what they will be able to accomplish in the Champions League. Having gone to Azerbaijan and almost dropping points agains Qarabag, Di Francesco and his squad have a lot to prove at the San Siro tomorrow. For their Champions League match on Wednesday, he lined up: Alisson; Juan Jesus, Manolas, Kolarov, Pers, Gonalons, Nainggolan, Pellegrini, Dzeko, El Shaarawy, and Defrel. Di Francesco has some new injuries to deal with, as Pellegrini has the flu, and Perotti and Defrel were injured on Wednesday. He will also be without Schick, Karsdorp, and Emerson, with Moreno in doubt as well.

Looking back to Sunday, for Roma's 3-1 win over Udinese, some kid with a paintbrush for hair scored a brace, I think he's called El Shaarawy. He is apparently already planning to score against his former club, informing everyone that he would not celebrate. Gee, thanks. You break our hearts, leave us, and promise not to be a jerk about hurting us more. Whatever with the Prodigal Son, you score against us, you are dead to me.

Speaking of hurting us more, Montella just loves his  dysfunctional 3-5-2 system. Because, you know, against competitive opponents, it works so well. And our defense is so solid. I mean with a four man backline, it was. But those are Trump level delusions to say this three man backline is working out. At least he will have Calabria and Montolivo back. Certainly, we could use the ex-captain's goal scoring prowess. But Montella will still be without Conti, obviously, and Antonelli is yet to clear fitness either.

Playing Roma is always a tough match. Despite playing at the San Siro, Milan are certainly the underdog in this one. But no one is under more scrutiny than Montella. A win would keep his job at least through Christmas and improve the mentality at the club so much. And a loss would put him under even more pressure, further decimate the already struggling mentality, and subject him to criticism and abuse that might be more harsh than deserved. For the Prodigal Son, it's a must win situation.

This post inspired by the music of Patrick Stump's "Who's the (Bat)Man"

Serie A Week 7
Milan vs. Roma
Sunday, October 1 • 18:00 CEST (12noon EDT)
This match will be shown on RAI and BeIN Sports in the U.S.