The 25-year-old has become one of Stuttgart’s most influential players since joining from Hoffenheim in 2023, earning nine senior caps for Germany and attracting attention from several major European clubs.
According to Tuttosport, AC Milan are assessing Stiller as they plan for the eventual departure of Modric, whose contract at San Siro runs until June 2027. The Croatian remains an important figure for the Italian side, but the club are already considering options for the future of their midfield.
Stiller is an established name on AC Milan’s recruitment list, having been monitored since late 2024. The report suggests that the expected arrival of Markus Krösche as the club’s new head of football could help revive their interest.
Krösche, formerly sporting director at Eintracht Frankfurt, is expected to begin his Milan role on 1 January 2027. His knowledge of the German market and contacts in the Bundesliga could prove useful if the Italian club decide to pursue Stiller.
The midfielder has a reported €40 million release clause in his Stuttgart contract, which runs until June 2028. However, his future at the Bundesliga club is uncertain. Sky Germany reported in October that there had been little progress in discussions over an extension and that Stiller could be considering a departure.
He is currently sidelined with an adductor injury, which has also affected his availability for Germany.
Milan are considering other midfield options, including Brighton’s Yasin Ayari and Bournemouth’s Alex Scott, so Stiller is not the only candidate under consideration. Nevertheless, his technical qualities and experience at the highest level make him an attractive option as the club plan their next major recruitment drive.
Any move remains at an early stage, with no reported negotiations between Milan and VfB Stuttgart. The coming months will determine whether Krösche’s arrival turns the club’s longstanding interest into a concrete pursuit.