Roma vs Milan a clash of close friends big clubs and reversing fortunes

Di Francesco, left, and Montella will put their friendship aside for Sunday’s must-win game at the San Siro.

Eusebio di Francesco and Vincenzo Montella have known each other for years. Most people remember them playing together for Roma’s last title-winning team in 2000-01, but the friendship between the two actually goes back even further to the very start of their careers.

Di Francesco and Montella were apprentices at Empoli. Just two kids, a long way from home, with the same goal of making it as professional footballers. Another teammate from back in the day, Nicola Caccia, is now Montella’s assistant, making Sunday’s game between Milan and Roma a sort of friends reunited. Of course, what goodwill they feel towards one another will not stop Di Francesco stepping over Montella, or vice-versa, in pursuit of their objectives this weekend. The result of this game will leave an echo over the international break and be pored over and picked apart for a fortnight. You might say it pits the underrated against the over-hyped.

If you weren’t downgrading Roma’s chances this year, you were a lonely voice. Many of the papers in Italy forecast them to regress, ruling the Giallorossi out of the battle for the title and even going so far as to argue they might face a scrap to remain in the top four. Talk about harsh.

The grounds for doing so were the loss of their record-breaking manager, Luciano Spalletti, to one of their rivals, the appointment of a candidate without experience of coaching a big club and the sales of Wojciech Szczesny, Antonio Rudiger and Mohamed Salah. Monchi’s first transfer window as Roma’s sporting director also wasn’t considered sexy enough until the signing of Patrik Schick, although even that didn’t completely silence the critics because of the assumption Salah would be replaced by another winger.

It paled in comparison with what Milan were doing around the same time, spending €230 million — three summers’ worth of budget in one –…

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