AC Milan is poised to hand Ruben Amorim a second chance on one of Europe’s biggest stages, and the move raises a fascinating question: Can a coach who flamed out spectacularly at Manchester United rediscover the touch that made him a two-time Portuguese champion?
The Rossoneri have agreed to a two-year contract with an option for the Portuguese manager, according to reports from Fabrizio Romano and Matteo Moretto. He will earn approximately €3 million per season, plus performance-based bonuses. The deal ends a coaching search that dragged on for weeks and saw the club circle multiple high-profile names.
A Coaching Carousel in the Background
Milan initially targeted Bournemouth’s Andoni Iraola, but Iraola opted to wait for a potential opening at Liverpool. The club then explored a range of candidates tied to the Red Bull ecosystem—Oliver Glasner and Matthias Jaissle among them—before eventually pivoting to Amorim. Along the way, Mauricio Pochettino and Arne Slot were also discussed internally.
Now that the coaching piece is in place, the club is expected to turn its attention to the front office. Milan has reportedly reached an agreement in principle with Eintracht Frankfurt to bring in director Markus Krosche and technical director Timmo Hardung. The catch? Both are still under contract in Germany, and Frankfurt may demand compensation to let them leave early.
The Amorim Rollercoaster
Amorim’s reputation took a serious hit during his brief stint at Manchester United. He was fired in January after just 47 games at the helm, with only 15 wins, 13 draws, and 19 losses on his record. When he took over in November 2025, the club was already struggling—but by the time he was shown the door, United had sunk to 15th in the Premier League table.
That ugly chapter stands in stark contrast to his time at Sporting CP, where he won back-to-back Primeira Liga titles and built a team that played fearless, aggressive football. The question for Milan is whether that Amorim still exists.
On paper, the stylistic fit is intriguing. Milan’s squad doesn’t require major overhauls to match his preferred high-pressing, vertical system. The Rossoneri have historically thrived when they play with pace and intensity—traits that defined Amorim’s best teams in Lisbon.
Still, there are real risks. The line between Amorim’s ultra-aggressive approach and outright chaos is thin. His Manchester United side often looked disorganized and vulnerable in transition, and critics wondered whether his system was sustainable at a club with higher expectations. Moreover, it’s a head-scratcher that Milan chose a coach and front-office executives who have never worked together before, especially when they had a rare opportunity to align a manager with a handpicked sporting structure.
Only time will tell if Amorim can recapture the magic at San Siro—or if his Old Trafford failure was a warning sign that this bet is riskier than it seems.
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