Donyell Malen has been nothing short of a sensation during his half-season at Roma.
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In Dante’s vision, the Inferno and Paradiso are not opposites but shades of the same journey—a measure of how far the soul has turned toward or away from love. Milan and Roma sit level on points in Serie A, seemingly worlds apart yet bound by shared frustrations: American ownership models, internal power struggles between coaches, sporting directors, and CEOs, and Champions League football dangling just out of reach, with millions at stake. One move, however, now separates them emotionally.
Both clubs hired experienced Italian coaches last summer, hoping Massimiliano Allegri and Gian Piero Gasperini would steer them back into the top four. Both tried to solve the equation laid out by legendary recruiter Pantaleo Corvino: you cannot build a competitive team, he argued, by signing the wrong goalkeeper or striker. Milan and Roma nailed the first part, locking down Mike Maignan and Mile Svilar, two of the world’s best No. 1s. But the second part baffled them. Santi Gimenez and Christopher Nkunku for one, Artem Dovbyk and Evan Ferguson for the other, failed to deliver. When a Gimenez-Dovbyk swap was floated last summer, it seemed almost like a joke about scoring goals. Milan have spent over €100m trying to replace Olivier Giroud. Roma haven’t had a reliable goal scorer since Tammy Abraham’s knee injury in 2023, and even he struggled with second-season syndrome.
Allegri and Gasperini found workarounds early this season. Rafa Leao and Christian Pulisic were unsustainably clinical in the first half, then regressed to the mean as Milan’s chance creation dried up. Roma, meanwhile, seemed the opposite of Gasperini’s high-scoring Atalanta sides. Clean sheets and narrow wins masked a goal shortage that eventually caught up with them. January offered both clubs another chance to crack the Corvino code.
Milan signed Niclas Fullkrug on loan from West Ham, but the deal was completed so early he’s been mostly forgotten. The Germany striker, who started a Champions League final less than two years ago, watched Allegri deploy wingers as center-forwards during a long goal drought. An agreement for Jean-Philippe Mateta also fell through after scans raised concerns about his knee. Milan remained stuck. Roma, however, finally found an answer. They broke Leon Bailey’s loan and brought in his Aston Villa teammate, Donyell Malen.
Malen has arguably been the best January signing since Fiorentina borrowed Mohamed Salah from Chelsea over a decade ago. He’s a late contender for Serie A MVP and has a slim chance of becoming Capocannoniere (the league’s top scorer) despite being in Italy for less than four months. No midwinter signing has been as prolific—not even Mario Balotelli when he left Manchester City for Milan in 2013. Memes compare him to R9 (Ronaldo Nazário), and fans kneel before him outside the Stadio Olimpico. He is the difference between Inferno and Paradiso right now. Malen has scored 13 Serie A goals, and his brace in a stunning 3-2 comeback at Parma has given Roma a faint hope of Champions League qualification. “I was starting to think about the Conference League,” Gasperini admitted.
Milan, meanwhile, are reluctantly eyeing that same competition. Malen’s 101st-minute winner came just as Milan prepared to face Atalanta at San Siro in a hostile atmosphere. Fans organized petitions and choreography demanding CEO Giorgio Furlani leave. Some have short memories: Furlani ran the club under former owners Elliott, the hedge fund that saved Milan from bankruptcy. Under his watch, Milan won the league and reached a Champions League semi-final, though Inter went on to the final at their expense. As for Roma, they still haven’t replaced Lina Souloukou, the CEO who resigned in 2024 after death threats following Daniele De Rossi’s sacking. For all the criticism of Milan’s structure, Roma have lacked a clear CEO figure ever since. Sporting directors have come and gone: Igli Tare’s future at Milan is uncertain, while Roma moved on Florent Ghisolfi after one season. His replacement, Frederic Massara, is expected to leave after Gasperini publicly criticized Roma’s recruitment, prompting Claudio Ranieri to clash with Gasperini and quit as senior advisor to the Friedkin Group. It wasn’t on the same level as Paolo Maldini’s dismissal at Milan, but Ranieri is a Romanista through and through.
Despite the scrutiny, Milan’s org chart looks relatively stable compared to Roma’s. The restlessness reflects both owners’ ambition. Qualifying for the Champions League is the minimum for RedBird and the Friedkin Group. Protests in Rome have been milder, surprisingly so after Ranieri’s exit, given the flak former owner James Pallotta caught for assembling competitive teams that finished runners-up to Juventus.
These stories offer a parable about Italian football. Roma and Milan’s owners have been portrayed as failing to assimilate with calcio culture, but they may have been too conformist. Hiring Mourinho, Gasperini, and Allegri was a gesture of understanding—a coach respected in the Italian context, not a German or Spaniard bringing novelty. These coaches are used to being the most important person at a club, accustomed to running things, and resistant to data and analytics. The media expects owners to let them run the show, acquiescing despite the changed economic landscape and UEFA financial regulations. Sign Paulo Dybala, loan Romelu Lukaku, provide Luka Modric a new home. By overcorrecting toward tradition, the onus falls on the coach to deliver. Gasperini has been more capable than Allegri in recent years. Milan have spiraled much like Juventus did in Allegri’s final season, even playing only once a week. Roma have come alive as Gasperini found a way to make them score like his Atalanta teams.
The momentum is with Roma, even though Milan’s destiny is in their hands. The tie-breaker separating fourth-placed Milan from fifth-placed Roma is their head-to-head record, which favors Allegri. But Milan next face Genoa, coached by Roma icon Daniele De Rossi. While Allegri and Tare agreed fans had a right to protest on Sunday, the timing felt like self-harm, creating a hostile environment for underperforming players. At 3-0 down in a 3-2 defeat to Atalanta, fans headed for the exits. If Milan are to get over the line, they need support in the final fortnight. Roma have the derby against Lazio, who could tire themselves out in Wednesday’s Coppa Italia final. If Lazio win a trophy and