David Moyes has bounced around the Premier League, but hasn’t landed a job as big as the United one since leaving. Ole Gunnar Solskjær spent nearly four years out of management before returning to manage Beşiktaş, where he was sacked after just eight months.
Erik ten Hag’s first gig post-United career went even worse. The Dutchman was appointed as the successor to Xabi Alonso at Bayer Leverkusen in the summer of 2025. But the hierarchy appeared to recognise that they had made a significant mistake straight away, dismissing Ten Hag three games into the Bundesliga season.
Can Ruben Amorim break the curse? Upon his appointment as United head coach in November 2024, the former Sporting boss had the world at his feet and the future looked bright.
Like so many before him, though, Amorim’s time at Old Trafford ended prematurely – but it didn’t take him too long to find an equally daunting new role.
Indeed, AC Milan unveiled Amorim as their new manager in June. For both parties, this appointment must work.
Milan require a reboot
In no uncertain terms, the previous two campaigns have been miserable experiences for the Rossoneri. A dismal eighth place finish during the 2024/25 season ensured Milan wouldn’t take part in any European competition last season.
Things didn’t exactly get much better last year. There may have been brief hope of a title challenge during the first half of the campaign, with Milan still sitting second as late on as Matchday 33, but seven defeats in their final 13 games ended the charge.
European football returns then, in the guise of the Europa League, with this being the fifth time Milan are set to feature in UEFA’s secondary club competition since 2017.
As such, a reboot is required, one that can take the club back to the summit of Serie A and secure a return to the Champions League in the process.
Amorim once stepped into the Old Trafford dugout with the same mission he now faces at San Siro: To restore a fallen giant.
In theory, Amorim’s appointment makes perfect sense for Milan. Turning this once great club back into serial winners is a passion project, something that the Portuguese is familiar with.
Sporting hadn’t won a league title since 2002 when Amorim, less than 18 months into his embryonic managerial career, made the move to the Estádio José Alvalade in March 2020.
When he departed two years later, Amorim had led Sporting to two league titles, two Portuguese League Cups and a Super Cup victory, the club’s greatest era since the early years of the 21st century.
Milan have been starved of success recently. A tally of three league titles in 22 years is a dreadful return for a club of this size. A European trophy hasn’t been won since 2007, while the Rossoneri’s last Coppa Italia triumph came in 2003.
Amorim will relish the challenge of taking Milan back to where they belong.
One thing is certain, however, Amorim must get a tune out of players who struggled during the second half of last season, notably Rafael Leão and Christian Pulisic.
Leão and Pulisic hold the keys to Milan’s revival
Although Milan finished eighth in 2024/25, Leão and Pulisic combined for 29 goals and 25 assists throughout the campaign.
That output collapsed to 20 goals and just seven assists last term as both players largely struggled to replicate the form of the previous season.
Leão only played 31 times in all competitions, while Pulisic made 34 appearances as both wingers suffered various injuries that disrupted their rhythm. Under Maxi Allegri, the duo were often shoehorned out of position in his 3-5-2 system, regularly playing as part of a front two rather than in their natural positions out wide.
Amorim is more likely to deploy a 3-4-3 system at Milan, which could see Leão and Pulisic feature as part of a front free, playing higher and wider, and more crucially, to their respective strengths. Of course, as is customary with Milan’s best players, there is speculation that the Portuguese will leave on a transfer but that has yet to pass (at the time of writing).
At Sporting, wingers Pote and Trincão were regularly used to support Viktor Gyökeres to devastating effect, forming one of the most effective front threes in European football.
Gonçalo Ramos will be Amorim’s main centre forward this season after arriving from PSG in a transfer worth £60m. Should Leão and Pulisic stay, and return to form under the former United boss, that front three could play havoc with Serie A defences.
If this budding relationship between Amorim and Milan is going to work, a positive start is essential. Matches against Torino and Venezia offer an ideal opportunity to seal six points, building some early momentum heading into September.
Given how poor the club ended last season, Amorim should be given time by the Milan hierarchy to bed in his ideas and get them playing to his own particular style.
Perfection isn’t required immediately, but signs of life must be on show in the opening few weeks of the campaign.
If the front three clicks and Milan get off to a fast start, the Rossoneri’s revival may arrive sooner than expected.
(Cover image from IMAGO)
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