Even without the distraction of European football, Massimiliano Allegri failed to steer AC Milan back to the UEFA Champions League on his return to San Siro in the 2025/26 season. The campaign ended in crushing fashion with a heartbreaking home loss to perennial strugglers Cagliari on the final weekend, a result that underscored the gulf between the club’s ambitions and its current reality. Allegri, who had been brought back to restore the Rossoneri’s status among Europe’s elite, instead delivered a season defined by inconsistency and missed opportunities, leaving the hierarchy to question whether their faith in the former Juventus boss was misplaced.
The defeat to Cagliari was emblematic of Milan’s broader struggles—an inability to break down determined defenses and a lack of cutting edge in decisive moments. Without the midweek demands of continental competition, Allegri had no excuse for the disjointed performances that plagued the squad. The board’s patience, already tested by a mid-season slide, now appears to be wearing thin as the club faces another summer of reconstruction rather than the Champions League windfall needed to accelerate its rebuild.
As Milan weigh their options, the stark reality is that Allegri’s second spell has yielded neither the style nor the substance that was promised. The pursuit of a former Manchester United manager—reports have linked the club with an approach for Erik ten Hag—raises the question of whether the Rossoneri are chasing a dream that no longer fits their financial and