In Dante, the Inferno is not so different from Paradiso. They compare better than they contrast. The line between them is subtler than expected. It is a spectrum of how far the soul has oriented itself toward or away from love. Milan and Roma are level on points in Serie A. The two seem dimensions apart and yet share so many things in common: exasperation with American ownership models, power struggles between coaches, sporting directors and chief executives, Champions League football tantalisingly within reach but agonisingly at risk. Tens of millions at stake.
Having said all that, one move separates them in sentiment.
Both clubs appointed experienced Italian coaches in the summer in the hope that Massimiliano Allegri and Gian Piero Gasperini would restore Milan and Roma to the top four. Both tried to solve the equation, as laid out by one of Italy’s great recruiters, Pantaleo Corvino, behind all competitive teams. You cannot, or so the Corvino theory holds, sign the wrong player in the goalkeeper and striker positions if you are to build a good side. It’s as simple as that. Milan and Roma nailed the first part. They extended Mike Maignan and Mile Svilar’s contracts, retaining a couple of the world’s best No 1s. Neither renewal should be taken for granted.
But the second part of the equation continued to flummox both. Santi Gimenez and Christopher Nkunku on the one hand, Artem Dovbyk and Evan Ferguson on the other, have underwhelmed. When a Gimenez-Dovbyk swap was mooted last summer, you would have been forgiven for thinking the goal was maybe not to score goals. Milan have spent more than €100m trying to replace Olivier Giroud. Roma have not had a regular goalscorer since Tammy Abraham’s knee injury in 2023 and even then, the Englishman was afflicted by second-season syndrome. A year later, Dovbyk replaced Abraham, who left on loan, as fate would have it, to Milan, where, truth be told, he fared no better before being returned to sender and ultimately sold to Besiktas.
At the start of this season, Allegri and Gasperini found workarounds. Rafa Leao and Christian Pulisic were unsustainably clinical in the first half of the season, before regressing to the mean in a side bereft of chance creation in the second half of the campaign. Roma, meanwhile, felt like the opposite of a free-scoring Gasperini team. Accustomed to his Atalanta sides racking up more than 100 goals a season, Roma were an anaemic alter ego. In their early and unexpected title challenge, they were keeping clean sheets and edging games by the narrowest of margins before a paucity of goals at the other end caught up with them.
January was a chance for both to have another go at cracking the Corvino code. Milan signed Niclas Fullkrug on loan from West Ham United. The deal was set up so early that he has largely been forgotten about. The Germany striker, who started a Champions League final less than two years ago, has been a spectator, watching Allegri play wingers as centre-forwards and persist with them through a goal drought. An agreement was also reached for Jean-Philippe Mateta in the final days of the winter, only for Milan to responsibly pull out after a series of scans left them with reservations about his knee. If a solution continued to elude Milan, Roma belatedly found one.
They rectified the issue by breaking Leon Bailey’s loan and taking on his Aston Villa team-mate, Donyell Malen, instead.
The Dutchman has arguably been the best January signing since Fiorentina borrowed Mohamed Salah from Chelsea a little over a decade ago. He is a late contender for Serie A MVP and has a slim chance of ending as Capocannoniere (Serie A’s top scorer) despite being in the league for less than four months. For context, no one has been as prolific as Malen in the history of midwinter transfers: not even Mario Balotelli when he left Manchester City for Milan in 2013. Memes have depicted him as R9, Ronaldo O Fenomeno. Fans encountering him outside the Stadio Olimpico have approached Malen on bended knee.
He is the difference between Inferno and Paradiso at the moment. Malen has scored 13 times in Serie A and his brace at the weekend in a remarkable late 3-2 comeback win away to Parma has made flesh of Roma’s faint chances of Champions League qualification. “I was beginning to think about the Conference League,” Gasperini admitted.
Donyell Malen has scored 14 goals in 18 games in all competitions for Roma (Alessandro Sabattini/Getty Images)
Milan are reluctantly having to contemplate it instead. Malen’s winner in the 101st minute came just as they were preparing to play Atalanta at San Siro in an already hostile environment. A petition and choreography were organised, demanding Milan chief executive Giorgio Furlani leave. Those who signed it have, in some cases, short memories. Furlani handled Milan for former owners Elliott, the hedge fund that saved the club from being wound up and forced to start over at the bottom of the football pyramid.
Working with his predecessor as chief executive, Ivan Gazidis, they won the league together. That and a run to the Champions League semi-finals in RedBird’s first year has been all too quickly forgotten (in part because Inter got to the final at their expense). As for Roma, it is worth pointing out that they have still not replaced Furlani’s equivalent, Lina Souloukou, following her resignation in 2024 amid death threats and other unsavoury scenes in the aftermath of sacking fan favourite Daniele De Rossi.
For all the criticism of Milan’s structure, Roma have largely lacked an obvious CEO figure (and therefore someone to petition) ever since. For all the uncertainty around Igli Tare’s future as Milan’s sporting director, Roma also moved on Florent Ghisolfi after a single season. His replacement, Frederic Massara, who worked for Milan under Elliott, is expected to leave after Gasperini publicly criticised Roma’s recruitment. This prompted Claudio Ranieri to clash with Gasperini and depart as senior advisor to Roma’s owners, The Friedkin Group, less than a year after moving from the dugout to the boardroom. It was not quite on the same level as Paolo Maldini’s dismissal as technical director of Milan a couple of years ago, and Roma have been through this before with James Pallotta and Francesco Totti, but Ranieri is Roman and Romanista through and through.
As such, Milan’s often scrutinised org chart looks relatively stable compared to Roma’s. The restlessness reflects the owners’ ambition to win. Contrary to local reporting, qualifying for the Champions League is not enough for RedBird and The Friedkin Group. It’s the minimum.
Milan fans spell “G. F. OUT” as they protest against CEO Giorgio Furlani (Marco Luzzani/Getty Images)
Protests in Rome have been milder than at Milan, surprisingly so after Ranieri’s exit and especially so for those who remember how much flak the old owner, Pallotta, caught for assembling more competitive teams that regularly finished runners-up to Juventus.
Both experiences serve as a parable that tells us something about Italian football. Roma and Milan’s owners have been portrayed as not culturally assimilating with calcio. If anything, though, they have perhaps been too conformist.
Hiring Jose Mourinho, Gasperini and Allegri was a gesture of understanding, a way of saying: here is a coach you understand, successful in your context, more acceptable than a German or a Spaniard who might bring some novelty; here is a coach used to being the most important person at a club, a totaliser, unused to and disinclined from acting on data and analytics.
The expectation in the media is that you let them run the thing. You acquiesce to everything, irrespective of the changed economic landscape of European football and the need to comply with UEFA’s financial regulations. You sign Paulo Dybala, loan Romelu Lukaku (as Roma did in the past) and supply Luka Modric with a new home.
In overcorrecting towards tradition, it is surely then up to the coach to deliver. Gasperini has been more capable of doing that than Allegri in recent years. Milan have spiralled just as Juventus did in his final season, despite playing only one game a week. Roma have come to life just as Gasperini has found a way to make Roma score like his Atalanta teams.
The momentum is with them, even if Milan’s destiny is in their hands. The principal tie-breaker separating the former in fourth place and Roma in fifth, their head-to-head record, is in Allegri’s favour. But Milan go to Genoa next, a team coached by De Rossi, a Roma icon.
While Allegri and Tare agreed the fans had a right to protest on Sunday, the timing felt like an act of self-harm as it hardly created an environment for underperforming players to perform in. At 3-0 down in a 3-2 defeat to Atalanta, supporters headed for the exits, leaving in droves. The players might not be worthy of it, but if Milan are to get over the line, they need support in the next fortnight. As for Roma, they have the derby coming up and must hope Lazio tire themselves out in Wednesday’s Coppa Italia final. If Lazio were to win it and somehow end a chaotic season with a piece of silverware, it would be as uncomfortable for Roma as Inter winning the league has been for Milan.
For owners still in limbo over what really works in Italy, answering the Corvino conundrum is simultaneously simple and perplexingly hard. The difference between being plunged into the Inferno and an ascent to Paradiso could be Malen over Milan or vice versa.