Allegri took charge of AC Milan in May 2025, with the club looking like genuine Champions League contenders for much of the campaign that followed. Despite that early promise, Milan finished the season in fifth place, meaning they will play in the Europa League next term rather than Europe's top competition.
Milan confirmed Allegri's departure at the end of May. Around the same time, Antonio Conte left Napoli, opening the door for transfer journalist Fabrizio Romano to report that Allegri is being lined up as his replacement at the Serie A champions.
Before any move to Naples can be finalised, Allegri must first reach an agreement with Milan to terminate his existing contract, which is worth €5m for the season that has just concluded.
Reports from Calciomercato.com suggest Allegri had initially sought €2m in compensation for himself, with a further €3m earmarked for the rest of his coaching staff as part of any settlement with Milan.
The latest reporting indicates Allegri is now considering walking away from any severance payment at all, a move that would allow him to begin work at Napoli without delay.
Allegri stands to earn around €4.5m per season at Napoli. The same report states Milan have offered to cover the difference between that figure and his current Milan contract, amounting to around €500,000.
By waiving his exit package entirely, Allegri would remove the final obstacle standing between Milan and Napoli reaching a swift resolution, allowing him to begin preparing for the new season with his new club without the contractual dispute dragging into the summer.
For Napoli, securing Allegri quickly carries obvious benefits, with pre-season planning, transfer targets and squad organisation all dependent on having a head coach in place as early as possible. For Milan, removing Allegri's contract from the books, even without compensation, allows the club to move forward with their own managerial search following a season that fell short of expectations.
The situation underlines how managerial transitions in Italian football often hinge as much on financial negotiations between clubs as they do on the willingness of the individuals involved, with Allegri's apparent readiness to sacrifice his own payout potentially the difference between a protracted standoff and a swift handover.