CM: Gasperini at Milan, Allegri at Roma – the background on what might have been

AC Milan and Roma face each other tonight at San Siro, with Massimiliano Allegri and Gian Piero Gasperini in opposite dugouts.

Allegri will take charge of Milan, with whom he is enjoying a second spell. Gasperini meanwhile is on the Roma hot seat, the club that he joined from Atalanta in the summer where he had been for many years. However, as Calciomercato.com recall, things could have been very different.

Max is red and yellow?

Allegri could have easily have been the Roma boss. In fact, he was close to becoming their manager last March, with Claudio Ranieri himself having worked to convince him to take over, before they eventually turned to Gasperini.

The Friedkins would have been happy with Allegri: a winner, with a strong personality, knowledgeable about Roma (thanks in part to friendships like that with Ubaldo Righetti), and ready to relaunch himself at a demanding club, accepting a two-year plan and a careful transfer window.

Allegri could have been Roma’s coach even earlier, when the Friedkins decided to focus their attention on José Mourinho in the 2020-21 season. Roma had just lost 2-0 at home to Napoli with a brace from Dries Mertens.

Photos: Marco Luzzani + Paolo Bruno/Getty Images

The Americans decided the time had come to part ways with Fonseca and, through an agent, contacted the Tuscan, who at the time had been sidelined for a year and a half after his successful stint at Juventus.

The appointment was scheduled but then postponed, and the situation made Allegri nervous, so much so that the deal ultimately fell through. At the time he would have gone back there, but wanted a €7m net salary, even if there was room to negotiate.

A few years ago, Walter Sabatini explained that Allegri had been close to taking over the Roma job on another occasion. In fact, on that occasion, there was a contract signed that the coach later failed to honour.

“I advised Allegri to leave Milan and join Roma. Then he didn’t come, he went to Juventus, and Roma reorganised with other coaches like Garcia and Spalletti. Did Allegri sign a contract? He didn’t honour it,” he said.

Gasp at Milan?

Gian Piero Gasperini was also linked with becoming Milan’s head coach. The first time was after Stefano Pioli’s departure, and the second after Sergio Conceicao’s spell.

It was beginning to appear that the Grugliasco-born coach would not renew his contract with Atalanta, following Luca Percassi’s comments, and this saw the Rossoneri spring into life.

Given his splendid work with the Nerazzurri, Furlani believed he was a good fit for the project, with a manager capable of turning everything he touches into gold. However, things turned out differently.