The winds of change may be sweeping through the San Siro once again, as multiple Italian sources report that the futures of AC Milan head coach Massimiliano Allegri and sporting director Igli Tare are hanging in the balance—and Champions League qualification might not be enough to save them.

According to Milan insider Carlo Pellegatti, Allegri's relationship with club CEO Giorgio Furlani has become increasingly strained in recent weeks. While the veteran coach's contract runs through June 2027—with an automatic extension to 2028 if the Rossoneri secure a top-four finish—that clause may prove irrelevant if the tension between the two key figures continues to simmer.

Calciomercato.com adds that Allegri and Furlani have held several meetings to discuss the club's long-term vision, but sources suggest they are far from aligned on the path forward. The disconnect has fueled speculation that Allegri could walk away regardless of where Milan finishes in the Serie A table.

Meanwhile, Tare's position is also under the microscope. Tuttomercatoweb reports that the club's major summer investments—particularly big-money signings Christopher Nkunku and Ardon Jashari—have yet to deliver the expected returns, placing the sporting director's track record under scrutiny. With pressure mounting, Milan may look to shake up their front office as well.

Interestingly, Atalanta's highly regarded sporting director, Tony D'Amico, remains a target for the Rossoneri after last summer's interest. However, La Dea is reportedly reluctant to part ways with their key executive, making any potential move a complicated negotiation.

For Milan fans, this uncertainty adds another layer of drama to an already pivotal season. Whether the club can stabilize its leadership or faces another summer of upheaval could define their trajectory for years to come.